CH580077A5 - Isothiocyanato-pyridine anthelmintics and defoliants - prepd from corresp amino-pyridines and eg isothiocyanate in presence of gaseous HCl - Google Patents

Isothiocyanato-pyridine anthelmintics and defoliants - prepd from corresp amino-pyridines and eg isothiocyanate in presence of gaseous HCl

Info

Publication number: CH580077A5
Authority: CH; Switzerland
Prior art keywords: isothiocyanopyridine; carbon atoms; opt; alkyl; halogen
Prior art date: 1972-08-10

Application number

CH1188672A

Other languages

German (de)

English (en)

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1972-08-10

Filing date

1972-08-10

Publication date

1976-09-30

1972-08-10 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1972-08-10 Priority to CH1188672A priority Critical patent/CH580077A5/de

1973-01-01 Priority to AR249494A priority patent/AR207744A1/es

1973-07-31 Priority to NL7310591A priority patent/NL7310591A/xx

1973-08-03 Priority to IL42902A priority patent/IL42902A/en

1973-08-07 Priority to DE19732339993 priority patent/DE2339993A1/de

1973-08-08 Priority to AU59045/73A priority patent/AU485463B2/en

1973-08-08 Priority to CA178,284A priority patent/CA1019738A/en

1973-08-08 Priority to US386796A priority patent/US3929806A/en

1973-08-09 Priority to AT700773A priority patent/AT334128B/de

1973-08-09 Priority to IT27725/73A priority patent/IT1003120B/it

1973-08-09 Priority to HUCI1400A priority patent/HU170391B/hu

1973-08-09 Priority to ES417715A priority patent/ES417715A1/es

1973-08-09 Priority to ZA735439A priority patent/ZA735439B/xx

1973-08-09 Priority to FR7329142A priority patent/FR2195443B1/fr

1973-08-09 Priority to BR6112/73A priority patent/BR7306112D0/pt

1973-08-09 Priority to BE134398A priority patent/BE803406A/fr

1973-08-09 Priority to GB3780773A priority patent/GB1440099A/en

1973-08-10 Priority to JP48089934A priority patent/JPS4962478A/ja

1975-10-10 Priority to US05/621,443 priority patent/US4001254A/en

1976-09-30 Publication of CH580077A5 publication Critical patent/CH580077A5/de

Links

150000003927 aminopyridines Chemical class 0.000 title claims description 3
230000000507 anthelmentic effect Effects 0.000 title abstract description 9
239000002837 defoliant Substances 0.000 title abstract description 4
WFJPRCMYUOOTNS-UHFFFAOYSA-N 2-isothiocyanatopyridine Chemical compound S=C=NC1=CC=CC=N1 WFJPRCMYUOOTNS-UHFFFAOYSA-N 0.000 title description 7
239000000921 anthelmintic agent Substances 0.000 title description 5
229940124339 anthelmintic agent Drugs 0.000 title description 4
150000002540 isothiocyanates Chemical class 0.000 title 1
241001465754 Metazoa Species 0.000 claims abstract description 31
239000002253 acid Substances 0.000 claims abstract description 22
150000003839 salts Chemical group 0.000 claims abstract description 19
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
229910052736 halogen Inorganic materials 0.000 claims abstract description 11
150000002367 halogens Chemical class 0.000 claims abstract description 11
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 8
125000001589 carboacyl group Chemical group 0.000 claims abstract description 7
231100000252 nontoxic Toxicity 0.000 claims abstract description 7
230000003000 nontoxic effect Effects 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
125000005110 aryl thio group Chemical group 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
125000001691 aryl alkyl amino group Chemical group 0.000 claims abstract description 4
125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
125000004104 aryloxy group Chemical group 0.000 claims abstract 4
125000001769 aryl amino group Chemical group 0.000 claims abstract 3
-1 cyano, hydroxy Chemical group 0.000 claims description 68
125000004432 carbon atom Chemical group C* 0.000 claims description 29
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 13
238000000034 method Methods 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 7
150000003222 pyridines Chemical class 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims description 3
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
150000008065 acid anhydrides Chemical class 0.000 claims description 2
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 claims description 2
150000001718 carbodiimides Chemical class 0.000 claims description 2
HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
125000004385 trihaloalkyl group Chemical group 0.000 claims description 2
241000196324 Embryophyta Species 0.000 abstract description 9
230000000694 effects Effects 0.000 abstract description 7
241000244206 Nematoda Species 0.000 abstract description 6
241000869417 Trematodes Species 0.000 abstract description 5
229910052757 nitrogen Inorganic materials 0.000 abstract description 3
235000010469 Glycine max Nutrition 0.000 abstract description 2
244000061456 Solanum tuberosum Species 0.000 abstract description 2
235000002595 Solanum tuberosum Nutrition 0.000 abstract description 2
240000006394 Sorghum bicolor Species 0.000 abstract description 2
235000011684 Sorghum saccharatum Nutrition 0.000 abstract description 2
235000021374 legumes Nutrition 0.000 abstract description 2
235000012015 potatoes Nutrition 0.000 abstract description 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 2
229920000742 Cotton Polymers 0.000 abstract 1
244000068988 Glycine max Species 0.000 abstract 1
244000299507 Gossypium hirsutum Species 0.000 abstract 1
241000244174 Strongyloides Species 0.000 abstract 1
125000003282 alkyl amino group Chemical group 0.000 abstract 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
239000002274 desiccant Substances 0.000 abstract 1
125000000623 heterocyclic group Chemical group 0.000 abstract 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
239000004480 active ingredient Substances 0.000 description 46
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
235000002639 sodium chloride Nutrition 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
125000001424 substituent group Chemical group 0.000 description 14
241000699670 Mus sp. Species 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
238000002474 experimental method Methods 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 10
239000000969 carrier Substances 0.000 description 9
239000012141 concentrate Substances 0.000 description 9
235000008504 concentrate Nutrition 0.000 description 9
239000006072 paste Substances 0.000 description 9
239000000843 powder Substances 0.000 description 9
239000011734 sodium Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
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 8
238000006243 chemical reaction Methods 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 7
229910000564 Raney nickel Inorganic materials 0.000 description 7
239000013543 active substance Substances 0.000 description 7
239000003513 alkali Substances 0.000 description 7
239000008187 granular material Substances 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
239000000126 substance Substances 0.000 description 7
241000242711 Fasciola hepatica Species 0.000 description 6
239000007868 Raney catalyst Substances 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002270 dispersing agent Substances 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
239000005457 ice water Substances 0.000 description 6
235000012054 meals Nutrition 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
239000000155 melt Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
241000204725 Ascaridia galli Species 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000000853 adhesive Substances 0.000 description 4
230000001070 adhesive effect Effects 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000007859 condensation product Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
238000011156 evaluation Methods 0.000 description 4
208000006275 fascioliasis Diseases 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
244000000013 helminth Species 0.000 description 4
210000000936 intestine Anatomy 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
238000012545 processing Methods 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241000287828 Gallus gallus Species 0.000 description 3
241001464384 Hymenolepis nana Species 0.000 description 3
206010061217 Infestation Diseases 0.000 description 3
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical class [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003674 animal food additive Substances 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
235000013330 chicken meat Nutrition 0.000 description 3
230000035613 defoliation Effects 0.000 description 3
229960003887 dichlorophen Drugs 0.000 description 3
ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 3
229960004068 hexachlorophene Drugs 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
229960001614 levamisole Drugs 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
XULACPAEUUWKFX-UHFFFAOYSA-N niclofolan Chemical compound C1=C(Cl)C=C([N+]([O-])=O)C(O)=C1C1=CC(Cl)=CC([N+]([O-])=O)=C1O XULACPAEUUWKFX-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000002245 particle Substances 0.000 description 3
229950000688 phenothiazine Drugs 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
239000000047 product Substances 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
ZLXHXXWFYGXTEP-UHFFFAOYSA-N 2-n-(4-methoxyphenyl)pyridine-2,5-diamine Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(N)C=N1 ZLXHXXWFYGXTEP-UHFFFAOYSA-N 0.000 description 2
DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 description 2
GQLIWFZGAFHTOH-UHFFFAOYSA-N 5-isothiocyanato-2-(4-methylphenyl)sulfonylpyridine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CC=C(N=C=S)C=N1 GQLIWFZGAFHTOH-UHFFFAOYSA-N 0.000 description 2
YGSFMZIJHMEICM-UHFFFAOYSA-N 5-isothiocyanato-2-phenoxypyridine Chemical compound N1=CC(N=C=S)=CC=C1OC1=CC=CC=C1 YGSFMZIJHMEICM-UHFFFAOYSA-N 0.000 description 2
WZUQSUVTMZICSF-UHFFFAOYSA-N 5-isothiocyanato-n-(4-methoxyphenyl)pyridin-2-amine Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(N=C=S)C=N1 WZUQSUVTMZICSF-UHFFFAOYSA-N 0.000 description 2
ZOCZPMIRVLOPBS-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonylpyridin-3-amine Chemical compound N1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 ZOCZPMIRVLOPBS-UHFFFAOYSA-N 0.000 description 2
LPJBBUAQGOGMAE-UHFFFAOYSA-N 6-benzylsulfanylpyridin-3-amine Chemical compound N1=CC(N)=CC=C1SCC1=CC=CC=C1 LPJBBUAQGOGMAE-UHFFFAOYSA-N 0.000 description 2
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QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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240000002024 Gossypium herbaceum Species 0.000 description 2
235000004341 Gossypium herbaceum Nutrition 0.000 description 2
241000243780 Heligmosomoides polygyrus Species 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
229920000168 Microcrystalline cellulose Polymers 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
239000002518 antifoaming agent Substances 0.000 description 2
HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
239000002585 base Substances 0.000 description 2
JFIOVJDNOJYLKP-UHFFFAOYSA-N bithionol Chemical compound OC1=C(Cl)C=C(Cl)C=C1SC1=CC(Cl)=CC(Cl)=C1O JFIOVJDNOJYLKP-UHFFFAOYSA-N 0.000 description 2
229960002326 bithionol Drugs 0.000 description 2
229960003475 cambendazole Drugs 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
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125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000011133 lead Substances 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000006028 limestone Substances 0.000 description 1
235000011477 liquorice Nutrition 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
229960003439 mebendazole Drugs 0.000 description 1
BAXLBXFAUKGCDY-UHFFFAOYSA-N mebendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CC=C1 BAXLBXFAUKGCDY-UHFFFAOYSA-N 0.000 description 1
229960000901 mepacrine Drugs 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
WPYAUWHHBNJZOJ-UHFFFAOYSA-N methyl n-[4-(3-isothiocyanatopyridin-2-yl)sulfanylphenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1SC1=NC=CC=C1N=C=S WPYAUWHHBNJZOJ-UHFFFAOYSA-N 0.000 description 1
XHCCHUNHYUMEAA-UHFFFAOYSA-N methyl n-[4-[(5-isothiocyanatopyridin-2-yl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1NC1=CC=C(N=C=S)C=N1 XHCCHUNHYUMEAA-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229960001952 metrifonate Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
FGGFIMIICGZCCJ-UHFFFAOYSA-N n,n-dibutyl-4-hexoxynaphthalene-1-carboximidamide Chemical compound C1=CC=C2C(OCCCCCC)=CC=C(C(=N)N(CCCC)CCCC)C2=C1 FGGFIMIICGZCCJ-UHFFFAOYSA-N 0.000 description 1
KDDZJYXJRLIQRC-UHFFFAOYSA-N n,n-diethyl-3-isothiocyanato-6-phenylmethoxypyridin-2-amine Chemical compound C1=C(N=C=S)C(N(CC)CC)=NC(OCC=2C=CC=CC=2)=C1 KDDZJYXJRLIQRC-UHFFFAOYSA-N 0.000 description 1
IVDFNMKQOLNNCF-UHFFFAOYSA-N n,n-diethyl-6-(4-isothiocyanatophenoxy)pyridin-2-amine Chemical compound CCN(CC)C1=CC=CC(OC=2C=CC(=CC=2)N=C=S)=N1 IVDFNMKQOLNNCF-UHFFFAOYSA-N 0.000 description 1
GSGQINQHLZFWMF-UHFFFAOYSA-N n-(3-isothiocyanatophenyl)pyridin-2-amine Chemical compound S=C=NC1=CC=CC(NC=2N=CC=CC=2)=C1 GSGQINQHLZFWMF-UHFFFAOYSA-N 0.000 description 1
IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 description 1
XIXLJZUEQLKOHU-UHFFFAOYSA-N n-(4-bromophenyl)-5-isothiocyanatopyridin-2-amine Chemical compound C1=CC(Br)=CC=C1NC1=CC=C(N=C=S)C=N1 XIXLJZUEQLKOHU-UHFFFAOYSA-N 0.000 description 1
NBSCIUKWKCYBPQ-UHFFFAOYSA-N n-(4-chlorophenyl)-5-isothiocyanatopyridin-2-amine Chemical compound C1=CC(Cl)=CC=C1NC1=CC=C(N=C=S)C=N1 NBSCIUKWKCYBPQ-UHFFFAOYSA-N 0.000 description 1
FGUQWQDEBGZVAD-UHFFFAOYSA-N n-(4-ethoxyphenyl)-5-isothiocyanatopyridin-2-amine Chemical compound C1=CC(OCC)=CC=C1NC1=CC=C(N=C=S)C=N1 FGUQWQDEBGZVAD-UHFFFAOYSA-N 0.000 description 1
HEKJVYBKLJPGNI-UHFFFAOYSA-N n-(4-fluorophenyl)-5-isothiocyanatopyridin-2-amine Chemical compound C1=CC(F)=CC=C1NC1=CC=C(N=C=S)C=N1 HEKJVYBKLJPGNI-UHFFFAOYSA-N 0.000 description 1
JOTCXRZXAMAECN-UHFFFAOYSA-N n-(4-iodophenyl)-5-isothiocyanatopyridin-2-amine Chemical compound C1=CC(I)=CC=C1NC1=CC=C(N=C=S)C=N1 JOTCXRZXAMAECN-UHFFFAOYSA-N 0.000 description 1
AURZZCNDQAILHQ-UHFFFAOYSA-N n-(4-isothiocyanatophenyl)-3-nitropyridin-2-amine Chemical compound [O-][N+](=O)C1=CC=CN=C1NC1=CC=C(N=C=S)C=C1 AURZZCNDQAILHQ-UHFFFAOYSA-N 0.000 description 1
ALMCAWRWLNNORP-UHFFFAOYSA-N n-(4-isothiocyanatophenyl)-4-methylpyridin-2-amine Chemical compound CC1=CC=NC(NC=2C=CC(=CC=2)N=C=S)=C1 ALMCAWRWLNNORP-UHFFFAOYSA-N 0.000 description 1
XQCXFAKTXBLVRA-UHFFFAOYSA-N n-(4-isothiocyanatophenyl)-5-nitropyridin-2-amine Chemical compound N1=CC([N+](=O)[O-])=CC=C1NC1=CC=C(N=C=S)C=C1 XQCXFAKTXBLVRA-UHFFFAOYSA-N 0.000 description 1
WWSCHNVDCTUGGK-UHFFFAOYSA-N n-(4-isothiocyanatophenyl)pyridin-2-amine Chemical compound C1=CC(N=C=S)=CC=C1NC1=CC=CC=N1 WWSCHNVDCTUGGK-UHFFFAOYSA-N 0.000 description 1
AZIAZCVTAHFXGH-UHFFFAOYSA-N n-(4-isothiocyanatophenyl)pyridin-4-amine Chemical compound C1=CC(N=C=S)=CC=C1NC1=CC=NC=C1 AZIAZCVTAHFXGH-UHFFFAOYSA-N 0.000 description 1
VXJRMJJSBXEAAW-UHFFFAOYSA-N n-[4-[(5-isothiocyanatopyridin-2-yl)amino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC1=CC=C(N=C=S)C=N1 VXJRMJJSBXEAAW-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
QNSIFYWAPWSAIJ-UHFFFAOYSA-N naftalofos Chemical compound C1=CC(C(N(OP(=O)(OCC)OCC)C2=O)=O)=C3C2=CC=CC3=C1 QNSIFYWAPWSAIJ-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
SGKGVABHDAQAJO-UHFFFAOYSA-N nitroxynil Chemical compound OC1=C(I)C=C(C#N)C=C1[N+]([O-])=O SGKGVABHDAQAJO-UHFFFAOYSA-N 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
210000000056 organ Anatomy 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
239000012074 organic phase Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
244000045947 parasite Species 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
KJKJUXGEMYCCJN-UHFFFAOYSA-N parathiazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CCN1CCCC1 KJKJUXGEMYCCJN-UHFFFAOYSA-N 0.000 description 1
229950011293 parathiazine Drugs 0.000 description 1
229950007337 parbendazole Drugs 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
NQQWFVUVBGSGQN-UHFFFAOYSA-N phosphoric acid;piperazine Chemical compound OP(O)(O)=O.C1CNCCN1 NQQWFVUVBGSGQN-UHFFFAOYSA-N 0.000 description 1
229960003506 piperazine hexahydrate Drugs 0.000 description 1
229960001954 piperazine phosphate Drugs 0.000 description 1
AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920001993 poloxamer 188 Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
244000144977 poultry Species 0.000 description 1
235000013594 poultry meat Nutrition 0.000 description 1
235000014483 powder concentrate Nutrition 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
229960003910 promethazine Drugs 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
229960005134 pyrantel Drugs 0.000 description 1
YSAUAVHXTIETRK-AATRIKPKSA-N pyrantel Chemical compound CN1CCCN=C1\C=C\C1=CC=CS1 YSAUAVHXTIETRK-AATRIKPKSA-N 0.000 description 1
229960002778 pyrvinium Drugs 0.000 description 1
GPKJTRJOBQGKQK-UHFFFAOYSA-N quinacrine Chemical compound C1=C(OC)C=C2C(NC(C)CCCN(CC)CC)=C(C=CC(Cl)=C3)C3=NC2=C1 GPKJTRJOBQGKQK-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
NEMNPWINWMHUMR-UHFFFAOYSA-N rafoxanide Chemical compound OC1=C(I)C=C(I)C=C1C(=O)NC(C=C1Cl)=CC=C1OC1=CC=C(Cl)C=C1 NEMNPWINWMHUMR-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000005070 ripening Effects 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
229940074353 santonin Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
239000000243 solution Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 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
125000005270 trialkylamine group Chemical group 0.000 description 1
KVSKGMLNBAPGKH-UHFFFAOYSA-N tribromosalicylanilide Chemical compound OC1=C(Br)C=C(Br)C=C1C(=O)NC1=CC=C(Br)C=C1 KVSKGMLNBAPGKH-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyridine Compounds (AREA)

CH1188672A 1972-08-10 1972-08-10 Isothiocyanato-pyridine anthelmintics and defoliants - prepd from corresp amino-pyridines and eg isothiocyanate in presence of gaseous HCl CH580077A5 (en)

Priority Applications (19)

Application Number	Priority Date	Filing Date	Title
CH1188672A CH580077A5 (en)	1972-08-10	1972-08-10	Isothiocyanato-pyridine anthelmintics and defoliants - prepd from corresp amino-pyridines and eg isothiocyanate in presence of gaseous HCl
AR249494A AR207744A1 (es)	1972-08-10	1973-01-01	Procedimiento para la preparacion de nuevos derivados de isotiocianopiridinas
NL7310591A NL7310591A (fr)	1972-08-10	1973-07-31
IL42902A IL42902A (en)	1972-08-10	1973-08-03	History of isothiocyanopyridine, preparation and veterinary preparations containing herbicides
DE19732339993 DE2339993A1 (de)	1972-08-10	1973-08-07	Kondensationsprodukte und ihre anwendung
AU59045/73A AU485463B2 (en)	1972-08-10	1973-08-08	New isothiocyanopyridine derivatives
CA178,284A CA1019738A (en)	1972-08-10	1973-08-08	Isothiocyanopyridine derivatives
US386796A US3929806A (en)	1972-08-10	1973-08-08	Isothiocyanopyridine derivatives
AT700773A AT334128B (de)	1972-08-10	1973-08-09	Verfahren zur bekampfung von parasitaren helminthen
IT27725/73A IT1003120B (it)	1972-08-10	1973-08-09	Iso tio cian piridine procedimen to per la loro preparazione e pro dotti antielmintici o per la de fogliazione e l essiccamento
HUCI1400A HU170391B (fr)	1972-08-10	1973-08-09
ES417715A ES417715A1 (es)	1972-08-10	1973-08-09	Procedimiento para la preparacion de isotiocianopiridinas.
ZA735439A ZA735439B (en)	1972-08-10	1973-08-09	New isothiocyanopyridine derivatives
FR7329142A FR2195443B1 (fr)	1972-08-10	1973-08-09
BR6112/73A BR7306112D0 (pt)	1972-08-10	1973-08-09	Osicoes antihelminticas e para o desfolhamento e dissecacao a base destas
BE134398A BE803406A (fr)	1972-08-10	1973-08-09	Isothiocyanato-pyridine, leur preparation et leurs applications
GB3780773A GB1440099A (en)	1972-08-10	1973-08-09	Isothiocyanopyridine derivatives
JP48089934A JPS4962478A (fr)	1972-08-10	1973-08-10
US05/621,443 US4001254A (en)	1972-08-10	1975-10-10	Isothiocyanopyridine derivatives

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1188672A CH580077A5 (en)	1972-08-10	1972-08-10	Isothiocyanato-pyridine anthelmintics and defoliants - prepd from corresp amino-pyridines and eg isothiocyanate in presence of gaseous HCl

Publications (1)

Publication Number	Publication Date
CH580077A5 true CH580077A5 (en)	1976-09-30

Family

ID=4377836

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1188672A CH580077A5 (en)	1972-08-10	1972-08-10	Isothiocyanato-pyridine anthelmintics and defoliants - prepd from corresp amino-pyridines and eg isothiocyanate in presence of gaseous HCl

Country Status (4)

Country	Link
BE (1)	BE803406A (fr)
BR (1)	BR7306112D0 (fr)
CH (1)	CH580077A5 (fr)
ZA (1)	ZA735439B (fr)

1972
- 1972-08-10 CH CH1188672A patent/CH580077A5/de not_active IP Right Cessation
1973
- 1973-08-09 BE BE134398A patent/BE803406A/fr unknown
- 1973-08-09 ZA ZA735439A patent/ZA735439B/xx unknown
- 1973-08-09 BR BR6112/73A patent/BR7306112D0/pt unknown

Also Published As

Publication number	Publication date
BR7306112D0 (pt)	1974-08-29
ZA735439B (en)	1974-07-31
BE803406A (fr)	1974-02-11

Legal Events

Date	Code	Title	Description
1979-05-15	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2815621C2 (fr)	1990-08-09
DE2259220A1 (de)	1973-06-14	Kondensationsprodukte und ihre anwendung
EP0230400A2 (fr)	1987-07-29	N-3-(5-Trifluorométhyl-pyridyl-2-oxy)phényl-N'-benzoylureds pour combattre des helminths chez le bétail
EP0167491A2 (fr)	1986-01-08	Dérivés d'acide thiobarbiturique
US4001254A (en)	1977-01-04	Isothiocyanopyridine derivatives
EP0135155B1 (fr)	1990-09-26	Dérivés d'acide barbiturique
DE2815675A1 (de)	1978-10-19	Anthelmintika
DE2129960A1 (de)	1971-12-30	Benzolderivate
DE2434183C2 (de)	1982-07-01	Substituierte Phenylisothioharnstoffe, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
EP0191474A1 (fr)	1986-08-20	Dérivés de l'acide barbiturique
CH580077A5 (en)	1976-09-30	Isothiocyanato-pyridine anthelmintics and defoliants - prepd from corresp amino-pyridines and eg isothiocyanate in presence of gaseous HCl
DE2800740A1 (de)	1978-07-13	Anthelmintika
CH642359A5 (en)	1984-04-13	Benzimidazole derivatives
DE2140496A1 (de)	1972-02-17	Sulfonyl benzimidazole und ihre Saure additionssalze, Verfahren zu ihrer Her stellung und Arzneipraparate
CH580078A5 (en)	1976-09-30	Isothiocyanato-pyridine anthelmintics and defoliants - prepd from corresp amino-pyridines and eg isothiocyanate in presence of gaseous HCl
DE2609574C3 (de)	1978-06-22	1 -^-Fluor-S-trifluormethylthiophenyD-piperazin, dessen Salze, Verfahren zu dessen Herstellung und Arzneimittel
DE1935338C2 (de)	1982-05-13	Isothiocyano-diphenylamine, Verfahren zu deren Herstellung und ein diese Verbindungen enthaltendes anthelminthisches Mittel
EP0102327A2 (fr)	1984-03-07	Dérivés de l'acide barbiturique comme anthelmintique
DE2325036C3 (de)	1980-11-06	Arylenverbindungen sowie diese enthaltende Wurmmittel
DE1568021C3 (de)	1973-09-20	Neue Isothiocyano diphenylather und diphenylthioather, deren Herstel lung und Mittel zur Bekämpfung parsi tarer Helminthen und zur Verhütung von Helminthiasen bei Mensch und Tier
CH565164A5 (en)	1975-08-15	Isocyanato-benzoxazoles-benzothiazoles and benimidazoles - as anthelmintics and antimicrobials
DE2720290A1 (de)	1977-11-17	Anthelmintische und fungizide verbindungen
DE2711945A1 (de)	1977-09-29	Neue benzimidazol-2-carbamat-derivate, verfahren zu deren herstellung und diese enthaltende zusammensetzungen
DE2147857A1 (de)	1973-05-30	Substituierte 6-phenyl-imidazo eckige klammer auf 2,1-b eckige klammer zu -thiazole
DE2410237A1 (de)	1974-09-12	Imidazo eckige klammer auf 4,5-b eckige klammer zu pyridine, verfahren zu ihrer herstellung und ihre verwendung