JPS646171B2 - - Google Patents

Info

Publication number: JPS646171B2
Authority: JP; Japan
Prior art keywords: active ingredient; mammals; toxic; acid addition; addition salt
Prior art date: 1979-08-11
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.): Expired

Application number

JP10271779A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5626883A (en

Inventor

Imuraa Rorufu

Burubado Hansu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

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.)

1979-08-11

Filing date

1979-08-11

Publication date

1989-02-02

1979-08-11 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1979-08-11 Priority to JP10271779A priority Critical patent/JPS5626883A/ja

1981-03-16 Publication of JPS5626883A publication Critical patent/JPS5626883A/ja

1989-02-02 Publication of JPS646171B2 publication Critical patent/JPS646171B2/ja

Status Granted legal-status Critical Current

Links

239000004480 active ingredient Substances 0.000 claims description 42
241001465754 Metazoa Species 0.000 claims description 31
239000000203 mixture Substances 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 21
238000000034 method Methods 0.000 claims description 19
241000255925 Diptera Species 0.000 claims description 16
241000124008 Mammalia Species 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 15
231100000252 nontoxic Toxicity 0.000 claims description 13
230000003000 nontoxic effect Effects 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 7
LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical group NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
244000144972 livestock Species 0.000 claims description 3
241000238631 Hexapoda Species 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
230000009885 systemic effect Effects 0.000 claims description 2
238000003672 processing method Methods 0.000 claims 2
239000000243 solution Substances 0.000 description 15
239000000843 powder Substances 0.000 description 14
-1 2-cyclopropylamino-4,6-diamino-s-triazine 2-cyclopropylamino-4-amino-6 -Chlor-s-triazine Chemical compound 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000969 carrier Substances 0.000 description 8
239000004540 pour-on Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
239000002270 dispersing agent Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000006072 paste Substances 0.000 description 5
239000007921 spray Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
238000009472 formulation Methods 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
239000007943 implant Substances 0.000 description 4
244000045947 parasite Species 0.000 description 4
150000003335 secondary amines Chemical class 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
241000283690 Bos taurus Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241000736227 Lucilia sericata Species 0.000 description 3
241001494479 Pecora Species 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
235000013601 eggs Nutrition 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 3
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
VPGSXIKVUASQIY-UHFFFAOYSA-N 1,2-dibutylnaphthalene Chemical class C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 VPGSXIKVUASQIY-UHFFFAOYSA-N 0.000 description 2
YBXAUCWDTLINED-UHFFFAOYSA-N 2-n-cyclopropyl-4-n-methyl-1,3,5-triazine-2,4,6-triamine Chemical compound CNC1=NC(N)=NC(NC2CC2)=N1 YBXAUCWDTLINED-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000692095 Cuterebra Species 0.000 description 2
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
241000202813 Dermatobia Species 0.000 description 2
241000202828 Dermatobia hominis Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000257176 Hypoderma <fly> Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000257162 Lucilia <blowfly> Species 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
241001414987 Strepsiptera Species 0.000 description 2
206010052428 Wound Diseases 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
239000008272 agar Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
229960002903 benzyl benzoate Drugs 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
230000037396 body weight Effects 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000007654 immersion Methods 0.000 description 2
210000004731 jugular vein Anatomy 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
230000000974 larvacidal effect Effects 0.000 description 2
230000001418 larval effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012669 liquid formulation Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
230000003071 parasitic effect Effects 0.000 description 2
230000024241 parasitism Effects 0.000 description 2
229940068886 polyethylene glycol 300 Drugs 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
PSUUJJDPUSEFPD-UHFFFAOYSA-N 2-n,4-n,6-n-tricyclopropyl-1,3,5-triazine-2,4,6-triamine Chemical compound C1CC1NC1=NC(NC2CC2)=NC(NC2CC2)=N1 PSUUJJDPUSEFPD-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241001524424 Andrena sericata Species 0.000 description 1
241001425390 Aphis fabae Species 0.000 description 1
241000257161 Calliphoridae Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
241000531134 Cuterebrinae Species 0.000 description 1
DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
241000283086 Equidae Species 0.000 description 1
241000283074 Equus asinus Species 0.000 description 1
241001331845 Equus asinus x caballus Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
241001660203 Gasterophilus Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241001194722 Hypoderma tarandi Species 0.000 description 1
241000159699 Hypodermatinae 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
239000005909 Kieselgur Substances 0.000 description 1
235000019738 Limestone Nutrition 0.000 description 1
208000006123 Myiasis Diseases 0.000 description 1
241000257191 Oestridae Species 0.000 description 1
241000543819 Oestrus ovis Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
241000282941 Rangifer tarandus Species 0.000 description 1
235000019484 Rapeseed oil Nutrition 0.000 description 1
208000035415 Reinfection Diseases 0.000 description 1
241001194723 Rhinoestrus Species 0.000 description 1
241000282887 Suidae Species 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
241000609107 Wohlfahrtia vigil Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052915 alkaline earth metal silicate Inorganic materials 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000000889 atomisation Methods 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
SWWQNNDPJXYCNJ-UHFFFAOYSA-N didodecylazanium;chloride Chemical compound Cl.CCCCCCCCCCCCNCCCCCCCCCCCC SWWQNNDPJXYCNJ-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000010433 feldspar Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
210000001214 frontal sinus Anatomy 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000006028 limestone Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
210000003928 nasal cavity Anatomy 0.000 description 1
210000001331 nose Anatomy 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000017448 oviposition Effects 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
238000009304 pastoral farming Methods 0.000 description 1
230000037368 penetrate the skin Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
210000003800 pharynx Anatomy 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000007781 pre-processing Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000004544 spot-on Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP10271779A 1979-08-11 1979-08-11 Compound and composition for treating mammal to expel parasite Granted JPS5626883A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP10271779A JPS5626883A (en)	1979-08-11	1979-08-11	Compound and composition for treating mammal to expel parasite

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP10271779A JPS5626883A (en)	1979-08-11	1979-08-11	Compound and composition for treating mammal to expel parasite

Publications (2)

Publication Number	Publication Date
JPS5626883A JPS5626883A (en)	1981-03-16
JPS646171B2 true JPS646171B2 (de)	1989-02-02

Family

ID=14335008

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP10271779A Granted JPS5626883A (en)	1979-08-11	1979-08-11	Compound and composition for treating mammal to expel parasite

Country Status (1)

Country	Link
JP (1)	JPS5626883A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57143430A (en) *	1981-02-27	1982-09-04	Nippon Kokan Kk <Nkk>	Manufacture of high tensile steel with weldability and >=50kg/mm2 strength
US8722674B2 (en) *	2007-08-31	2014-05-13	Hanall Biopharma Co., Ltd.	1,3,5-triazine-2,4,6-triamine compound or pharmaceutical acceptable salt thereof, and pharmaceutical composition comprising the same

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH609835A5 (en) *	1976-08-19	1979-03-30	Ciba Geigy Ag	Pesticide

1979
- 1979-08-11 JP JP10271779A patent/JPS5626883A/ja active Granted

Also Published As

Publication number	Publication date
JPS5626883A (en)	1981-03-16

Publication	Publication Date	Title
DE2815621C2 (de)	1990-08-09
TWI383748B (zh)	2013-02-01	有機化合物
EP0573883A1 (de)	1993-12-15	Verwendung von 3-arylsubstituierten 5-Alkyl-isoxazol-4-carbonsäurederivaten zur Bekämpfung von Endoparasiten, neue 3-arylsubstituierte-5-Alkyl-isoxazol-4-carbonsäurederivate und Verfahren zu ihrer Herstellung
KR101926281B1 (ko)	2018-12-06	신규 술포닐아미노벤즈아미드 화합물
US4187304A (en)	1980-02-05	Procedure for treating mammals to control parasitic diptera larvae
US5416102A (en)	1995-05-16	Method of preventing the reinfestation of dogs and cats by fleas
JPS646171B2 (de)	1989-02-02
JPS6054314B2 (ja)	1985-11-29	新規チアゾリン、その製造方法及び該化合物を含むダニ類防除用組成物
JPH02164873A (ja)	1990-06-25	置換１，３，５―トリアジントリオン類、それらの製造方法及び寄生性原生動物に対する用途
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DK156196B (da)	1989-07-10	Fremgangsmaade til fremstilling af et tetramisol eller lavamisol paahaeldningspraeparat
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JPH0347250B2 (de)	1991-07-18
GB2057262A (en)	1981-04-01	Veterinary depot preparation with prolonged release of insecticide
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JPS6126762B2 (de)	1986-06-21