JPH0579647B2 - - Google Patents
Info
- Publication number
- JPH0579647B2 JPH0579647B2 JP16098983A JP16098983A JPH0579647B2 JP H0579647 B2 JPH0579647 B2 JP H0579647B2 JP 16098983 A JP16098983 A JP 16098983A JP 16098983 A JP16098983 A JP 16098983A JP H0579647 B2 JPH0579647 B2 JP H0579647B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- atom
- alkyl group
- animal
- 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.)
- Expired - Lifetime
Links
- 241001465754 Metazoa Species 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 11
- 241000238876 Acari Species 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 8
- 244000078703 ectoparasite Species 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000013057 ectoparasiticide Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- RFEJUZJILGIRHQ-XRIOVQLTSA-N 2,3-dihydroxybutanedioic acid;3-[(2s)-1-methylpyrrolidin-2-yl]pyridine Chemical compound OC(=O)C(O)C(O)C(O)=O.OC(=O)C(O)C(O)C(O)=O.CN1CCC[C@H]1C1=CC=CN=C1 RFEJUZJILGIRHQ-XRIOVQLTSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 244000144972 livestock Species 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 27
- 239000000203 mixture Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 241001674048 Phthiraptera Species 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 241001480803 Hyalomma Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001191175 Hyalomma detritum Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000238680 Rhipicephalus microplus Species 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 150000002903 organophosphorus compounds Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 241000238679 Amblyomma Species 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241001251778 Hyalomma truncatum Species 0.000 description 2
- 241000801118 Lepidium Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241001480755 Otobius Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- -1 phosphate ester Chemical class 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002728 pyrethroid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CVOBIOVONMMYGZ-UHFFFAOYSA-N 1-tert-butyl-4-(1-chloroethyl)benzene Chemical compound CC(Cl)C1=CC=C(C(C)(C)C)C=C1 CVOBIOVONMMYGZ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GLGQMFICPMIOHO-UHFFFAOYSA-N 2-tert-butyl-4-chloro-5-sulfanylpyridazin-3-one Chemical compound CC(C)(C)N1N=CC(S)=C(Cl)C1=O GLGQMFICPMIOHO-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000238682 Amblyomma americanum Species 0.000 description 1
- 241000565156 Amblyomma gemma Species 0.000 description 1
- 241000238888 Argasidae Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241001307956 Chorioptes bovis Species 0.000 description 1
- 241000202814 Cochliomyia hominivorax Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241001128002 Demodex canis Species 0.000 description 1
- 241001481695 Dermanyssus gallinae Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241001660201 Gasterophilus intestinalis Species 0.000 description 1
- 241000726221 Gemma Species 0.000 description 1
- 241001480796 Haemaphysalis Species 0.000 description 1
- 241000179420 Haemaphysalis longicornis Species 0.000 description 1
- 241000894055 Haematopinus eurysternus Species 0.000 description 1
- 241000670091 Haematopinus suis Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241001480805 Hyalomma dromedarii Species 0.000 description 1
- 241001480807 Hyalomma marginatum Species 0.000 description 1
- 241000238681 Ixodes Species 0.000 description 1
- 241000238889 Ixodidae Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001113970 Linognathus Species 0.000 description 1
- 241000322738 Menacanthus Species 0.000 description 1
- 241000543819 Oestrus ovis Species 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- 241000273374 Ornithonyssus sylviarum Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241001480756 Otobius megnini Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 241001481703 Rhipicephalus <genus> Species 0.000 description 1
- 241001378684 Rhipicephalus <subgenus> Species 0.000 description 1
- 241001481704 Rhipicephalus appendiculatus Species 0.000 description 1
- 241000864246 Rhipicephalus decoloratus Species 0.000 description 1
- 241001481696 Rhipicephalus sanguineus Species 0.000 description 1
- 241000257190 Sarcophaga <genus> Species 0.000 description 1
- 241000509427 Sarcoptes scabiei Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241001259048 Trichodectes canis Species 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 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 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 230000001776 parthenogenetic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002743 phosphorus functional group Chemical group 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
本発明はピリダジノン誘導体を有効成分として
含有する動物の外部寄生虫駆除剤に関するもので
ある。動物、例えば牛、馬、羊、豚などの家畜
類、家禽類、犬、猫などの動物の飼育において、
これらの動物に寄生する各種ダニ類、シラミ類、
ハエ類などの外部寄生虫が病原菌の運搬害虫とな
り、しばしば、これらの動物に悪影響を及ぼして
いる。
従来、動物の外部寄生虫駆除剤としては、ピレ
スロイド系化合物、カーバメート系化合物、有機
燐系化合物などの薬剤が知られているが、近年、
多種のダニ類がこれらの薬剤に対して、耐性を示
すに至り、新たな薬剤の開発が望まれており、特
に、上記のピレスロイド系、カーバメート系およ
び有機燐系に属しない新規な骨格構造を有する優
れた駆除剤の出現が強く望まれている現状にあ
る。
本発明は、新規ピリダジノン誘導体を含有する
動物の外部寄生虫の駆除剤に関するものである
が、従来数多くのピリダジノン系化合物の中で動
物の外部寄生虫に対して殺虫あるいは殺ダニ活性
を有するのとして例えば下記の式()で表され
る化合物が知られており、また農園芸用殺虫、殺
ダニ活性を有するものとして、例えば下記の式
()および式()で表される化合物が知られ
ている。
しかしながら、式()、式()および式
()で表される化合物はいずれも分子内に燐酸
エステルを含有している従来の有機燐系に属する
化合物群である。
式():
The present invention relates to an animal ectoparasiticide containing a pyridazinone derivative as an active ingredient. When raising animals, such as livestock such as cows, horses, sheep, and pigs, poultry, dogs, and cats,
Various mites and lice that parasitize these animals,
Ectoparasites such as flies serve as carriers of pathogens and often have negative effects on these animals. Conventionally, drugs such as pyrethroid compounds, carbamate compounds, and organophosphorus compounds have been known as ectoparasiticides for animals, but in recent years,
Many species of mites have become resistant to these drugs, and there is a desire to develop new drugs.In particular, drugs with new skeletal structures that do not belong to the above-mentioned pyrethroid, carbamate, and organophosphorus compounds are desired. At present, there is a strong desire for the emergence of an excellent insecticide that has the following properties. The present invention relates to an agent for killing animal ectoparasites containing a novel pyridazinone derivative, which is known to have insecticidal or acaricidal activity against animal ectoparasites among the many pyridazinone compounds. For example, compounds represented by the following formula () are known, and compounds represented by the following formula () and formula () are known as having insecticidal and acaricidal activity for agricultural and horticultural purposes. There is. However, the compounds represented by formula (), formula (), and formula () are all a group of compounds belonging to the conventional organic phosphorus group containing a phosphoric acid ester in the molecule. formula():
【式】ピリダフエンチ オン(商品名:オフナツク) 式():[Formula] Pyrida Huenchi On (Product name: Off Natsuku) formula():
【式】(西独特許第
2732101号公報参照)
(式中、R3,R4は低級アルキル基を、Zは酸
素原子または硫黄原子を表す。)
式():[Formula] (See West German Patent No. 2732101) (In the formula, R 3 and R 4 represent a lower alkyl group, and Z represents an oxygen atom or a sulfur atom.) Formula ():
一方、分子内に燐酸エステルを含有しないピリ
ダジノン系化合物としては、例えば下記の式
()、式()および式()で表される化合物
が知られている。
式()および式()で表される化合物は除
草剤、植物生長調節剤として有用であることが記
載されており、式()で表わされる化合物は農
園芸用殺菌剤として有用であること記載されてい
るだけで、殺虫活性および殺ダニ活性を有するこ
とは全く知られていないもので、まして、動物の
外部寄生虫に対して活性を有することは全く記載
されていない。
式():
On the other hand, as pyridazinone compounds that do not contain a phosphate ester in the molecule, compounds represented by the following formulas (), (), and () are known, for example. It is stated that the compounds represented by formula () and formula () are useful as herbicides and plant growth regulators, and that the compound represented by formula () is useful as agricultural and horticultural fungicides. However, it is not known at all that it has insecticidal or acaricidal activity, and furthermore, it has not been described at all that it has activity against animal ectoparasites. formula():
【式】(特公昭38−7998号公報
参照)
(式中、R1はアルキル基またはフエニル残基
を、R2は水素原子、メトキシ基、(中略)を表
す。)
式():[Formula] (Refer to Japanese Patent Publication No. 38-7998) (In the formula, R 1 represents an alkyl group or a phenyl residue, and R 2 represents a hydrogen atom, a methoxy group, (omitted).) Formula ():
【式】(特公昭40−3798号公報
参照)
(式中、R1は水素原子またはフエニル残基を、
R2はアルキル基、(中略)を表す。)
式():[Formula] (Refer to Japanese Patent Publication No. 40-3798) (In the formula, R 1 is a hydrogen atom or a phenyl residue,
R 2 represents an alkyl group (omitted). ) Formula ():
【式】(特開昭58−85869号公
報参照)
(式中、R1はアルキル基、(中略)、R2は塩素
原子、(中略)、R3は水素原子、アルキル基、(中
略)、XはSOまたはSO2を表す。)
本発明者らは、従来の有機燐系化合物に属しな
い化合物、例えば燐酸エステルを分子内に含有し
ないピリダジノン系化合物について種々探索研究
した結果、動物の外部寄生虫駆除剤として非常に
優れた新規ピリダジノン誘導体を見い出し、本発
明を完成したものである。
本発明は、一般式():[Formula] (Refer to JP-A-58-85869) (In the formula, R 1 is an alkyl group, (omitted), R 2 is a chlorine atom, (omitted), R 3 is a hydrogen atom, an alkyl group, (omitted) , X represents SO or SO 2. ) The present inventors have conducted various exploratory research on compounds that do not belong to conventional organophosphorus compounds, such as pyridazinone compounds that do not contain phosphoric acid esters in their molecules. The present invention was completed by discovering a new pyridazinone derivative that is extremely effective as a parasitic agent. The present invention is based on the general formula ():
【化】
〔式中、Rは直鎖または分岐を有するアルキル
基を、R1,R2はそれぞれ独立に水素原子または
低級アルキル基を示し、R3はハロゲン原子、低
級アルキル基、シクロアルキル基、低級アルコキ
シ基、低級ハロアルキル基、低級ハロアルコキシ
基、シアノ基、トリメチルシリル基、ニトロ基、
[In the formula, R represents a linear or branched alkyl group, R 1 and R 2 each independently represent a hydrogen atom or a lower alkyl group, and R 3 represents a halogen atom, a lower alkyl group, or a cycloalkyl group. , lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, cyano group, trimethylsilyl group, nitro group,
【式】【formula】
【式】また は[Formula] Also teeth
【式】(ただし、Xはハロゲン
原子、低級アルキル基、シクロアルキル基、低級
アルコキシ基、低級ハロアルキル基、低級ハロア
ルキル基、シアノ基またはニトロ基を、mは0ま
たは1〜5の整数を示し、mが2〜5の場合はX
は同一でも互いに異なつてもよい。)を示し、n
は0または1〜5の整数を示し、nが2〜5の場
合はR3は同一でも互いに異なつてもよい。R4は
ハロゲン原子を示し、Zは酸素原子または硫黄原
子を示す。〕で表されるピリダジノ誘導体(以下、
本発明化合物という。)の1種または2種以上を
有効成分として含有する動物用外部寄生虫駆除剤
に関するものである。
本発明の新規ピリダジノンの構造上の特徴点と
しては、ピリダジノン環の2−位のRがアルキル
基であつて、かつ5−位が置換されていてもよい
アラアルキルオキシ基またはアラアルキルチオ基
である点である。
特にRがターシヤリー・ブチル基が好ましく、
R4が塩素原子でR1が水素原子である場合がよい。
次に、本発明化合物は反応式()に示す方法
により製造することができる。すなわち、一般式
()で表される3(2H)−ピリダジノン誘導体と
一般式()で表されるベンジルハライド類を適
当な溶媒中、ハロゲン化水素吸収剤の存在下で反
応させて、製造することができる。[Formula] (where, If m is 2 to 5, then
may be the same or different. ), n
represents 0 or an integer of 1 to 5, and when n is 2 to 5, R 3 may be the same or different. R 4 represents a halogen atom, and Z represents an oxygen atom or a sulfur atom. ] Pyridazino derivatives (hereinafter referred to as
It is called a compound of the present invention. This invention relates to an animal ectoparasiticide containing one or more of the following as active ingredients. The structural features of the novel pyridazinone of the present invention include that R at the 2-position of the pyridazinone ring is an alkyl group, and the 5-position is an optionally substituted aralkyloxy group or an aralkylthio group. It is a point. In particular, R is preferably a tertiary butyl group,
It is preferable that R 4 is a chlorine atom and R 1 is a hydrogen atom. Next, the compound of the present invention can be produced by the method shown in reaction formula (). That is, it is produced by reacting a 3(2H)-pyridazinone derivative represented by the general formula () with a benzyl halide represented by the general formula () in an appropriate solvent in the presence of a hydrogen halide absorbent. be able to.
【化】
(ただし、反応式()においてR,R1,R2,
R3,R4,Zおよびnは前記と同じ意味を示し、
halはハロゲン原子を示す。)
反応溶媒としては低級アルコール(メタノー
ル、エタノール等)、ケトン類(アセトン、メチ
ルエチルケトン等)、炭化水素(ベンゼン、トル
エン等)、エーテル類(イソプロピルエーテル、
テトラヒドロフラン、1,4−ジオキサン等)お
よびアミド類(N,N−ジメチルホルムアミド
等)を使用することができる。しかし、溶解度、
副反応の可能性を考慮すると、N,N−ジメチル
ホルムアミド、芳香族炭化水素が好ましい。ハロ
ゲン化水素吸収剤としては無機塩基(例えば水酸
化ナトリウム、水酸化カリウム、炭酸ナトリウ
ム、炭酸カリウム、炭酸水素ナトリウム等)およ
び有機塩基(例えばトリエチルアミン、ピリジン
等)を用いることができる。反応温度は室温か
ら、使用する溶媒の沸点までの範囲をとることが
できるが、60℃〜150℃の範囲が望ましい。()
と()の比率は任意に設定できるが、等モルま
たはそれに近い比率で反応を行うのが有利であ
る。
本発明化合物は反応式(2)に示す方法によつても
製造することができる。[Chemical formula] (However, in reaction formula (), R, R 1 , R 2 ,
R 3 , R 4 , Z and n have the same meanings as above,
hal indicates a halogen atom. ) Reaction solvents include lower alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), hydrocarbons (benzene, toluene, etc.), ethers (isopropyl ether,
Tetrahydrofuran, 1,4-dioxane, etc.) and amides (N,N-dimethylformamide, etc.) can be used. However, solubility,
Considering the possibility of side reactions, N,N-dimethylformamide and aromatic hydrocarbons are preferred. Inorganic bases (eg, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, etc.) and organic bases (eg, triethylamine, pyridine, etc.) can be used as the hydrogen halide absorbent. The reaction temperature can range from room temperature to the boiling point of the solvent used, but is preferably in the range of 60°C to 150°C. ()
Although the ratio of () and () can be set arbitrarily, it is advantageous to carry out the reaction at an equimolar ratio or a ratio close to it. The compound of the present invention can also be produced by the method shown in reaction formula (2).
【化】
ただし、反応式(2)においてR,R1,R2,R3,
R4,Z,halおよびnは前記と同じ意味を示す。
次に本発明化合物の製造法を合成例を挙げて具
体的に説明するがこれらのみに限定されるもので
はない。
合成例 1
2−t−ブチル−4−クロロ−5−(4−t−
ブチル−α−メチルベンジルチオ)−3(2H)−ピ
リダジノン(化合物番号5)の製造
2−t−ブチル−4−クロロ−5−メルカプト
−3(2H)−ピリダジノン1.5gをN,N−ジメチ
ルホルムアミド10mlに溶解し、無水炭酸ナトリウ
ム10gおよび4−t−ブチル−α−メチル−ベン
ジルクロライド1.4gを加えて80〜110℃で2時間
加熱撹拌した。室温に冷却し、水100mlをくわえ
て撹拌した。析出した固体を濾取、水洗、乾燥
し、エタノールから再結晶して白色針状結晶を得
た(収率72.7%)。
mp:100〜106℃
1H−NMR(CDCl3),δ(ppm)4.58(t,1)
合成例1と同様にして第1表の本発明化合物を製
造した。[Chemical formula] However, in reaction formula (2), R, R 1 , R 2 , R 3 ,
R 4 , Z, hal and n have the same meanings as above. Next, the method for producing the compound of the present invention will be specifically explained with reference to synthesis examples, but the method is not limited thereto. Synthesis example 1 2-t-butyl-4-chloro-5-(4-t-
Production of butyl-α-methylbenzylthio)-3(2H)-pyridazinone (compound number 5) 1.5 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone was added to N,N-dimethyl The mixture was dissolved in 10 ml of formamide, 10 g of anhydrous sodium carbonate and 1.4 g of 4-t-butyl-α-methyl-benzyl chloride were added, and the mixture was heated and stirred at 80 to 110°C for 2 hours. The mixture was cooled to room temperature, added with 100 ml of water, and stirred. The precipitated solid was collected by filtration, washed with water, dried, and recrystallized from ethanol to obtain white needle crystals (yield 72.7%). mp: 100-106°C 1H-NMR (CDCl 3 ), δ (ppm) 4.58 (t, 1) The compounds of the present invention shown in Table 1 were produced in the same manner as in Synthesis Example 1.
【表】【table】
【表】
本発明化合物を動物の外部寄生虫の駆除に使用
するための施用方法は、特に限定されるものでは
ないが、局所的投与方法が好ましい。局所的投与
方法とは、例えば本発明化合物を含有する粉末も
しくは、本発明化合物をそのまま動物に直接振り
かけたり、動物の部分的または全体的に塗布した
り、また水和剤、乳剤形態のものを水で希釈し、
スプレーで噴霧したり、プールに薬剤を投与し、
動物を薬浴させたりする方法である。
本発明の駆除剤の形態としては、本発明化合物
をそのまま使用してもよいし、適当な補助剤、例
えば担体および添加剤と一緒に使用してもよい。
この担体および添加剤は、固体でも液体でもよ
く、調剤技術上で通常使用される物質例えば天然
物質、再生物質、有機溶媒および分散剤などが挙
げられる。
固体担体としては、例えばクレー、タルク、ベ
ントナイト、珪藻土等が挙げられ、液体担体とし
ては、水、アルコール類(メタノール、エタノー
ル等)、芳香族炭化水素類(ベンゼン、トルエン、
キシレン等)、塩素化炭化水素類、エーテル類、
ケトン類、エステル類(酢酸エチル等)、酸アミ
ド類(ジメチルホルムアミド等)などが挙げら
れ、必要に応じて、乳化剤、分散剤、懸濁剤、浸
透剤、展着剤、安定剤などを添加し、溶液、乳
剤、水和剤、粉剤等任意の剤型にて実用に供する
ことができる。
上記の溶液とは、例えば塗布方法に使用するた
めに、パラフイン油、トウモロコシ油またはナタ
ネ油中に有効成分を加えたものを意味する。また
必要に応じて、製剤または処理時に、他の動物
薬、共力剤などと混合させた組成物を使用しても
よい。
本発明化合物の使用量は、処理すべき対象の動
物の状態、種属、環境並びに所望する結果によつ
て、種々変わるが、一般的には、例えば水で希釈
して、有効成分濃度が0.002〜5重量%(20〜
50000ppm)、特に0.01〜0.1重量%(100〜
1000ppm)の希釈液を使用するのが好ましい。
次に本発明の駆除剤の配合例の若干を具体的に
挙げて示すが、これらのみに限定されるものでは
ない。なお、以下の配合例において「部」は重量
部を意味する。
配合例1 乳剤
有効成分(本発明化合物) 50部
キシレン 25部
N,N−ジメチルホルムアミド 20部
ソルポール2680 5部
(非イオン性界面活性剤とアニオン性界面活
性剤との混合物:東邦化学工業(株)商品名)
以上を均一に混合して乳剤とする。
配合例2 水和剤
有効成分(本発明化合物) 25部
ジークライトPFP 69部
(カオリン系クレー:ジークライト工業(株)商
品名)
ソルポール5039 3部
(非イオン性界面活性剤とアニオン性界面活
性剤との混合物:東邦化学工業(株)商品名)
カープレツクス(固結防止剤) 3部
界面活性剤とホワイトカーボンの混合物:塩
野義製薬(株)商品名)
以上を均一に混合粉砕して水和剤とする。
配合例3 粉剤
有効成分(本発明化合物) 3部
カープレツクス(固結防止剤) 0.5部
(界面活性剤とホワイトカーボンの混合物:
塩野義製薬(株)商品名)
クレー(群馬産) 95部
リン酸ジイソプロピル 1.5部
以上を均一に混合粉砕して粉剤とする。
次に、本発明化合物が卓効を示す動物の外部寄
生虫としては、マダニ類、ヒゼンダニ類、シラミ
類、双翅目害虫、半翅目害虫などが挙げられる。
具体的に以下に例示する。
マダニ類としては、
(1) マダニ科(Ixodidae)
ウシマダニ属(Boophilus)
オウシマダニ(Boophilus microplus)
ブーフイラス・デコロレイタス(Boophilus
decoloratus)
ブーフイラス・アニユレイタス(Boophilus
annulatus)
キララマダニ属(Amblyomma)
アンブリオンマ・バリエゲイタム
(Amblyomma variegatum)
アンブリオンマ・ハーブロイム
(Amblyomma herbraeum)
アンブリオンマ・ポンポサム(Amblyomma
pomposum)
アンブリオンマ・アメリカナム
(Amblyomma americanum)
アンブリオンマ・マクレイタム
(Amblyomma maculatum)
アンブリオンマ・ジエンマ(Amblyomma
gemma)
アンブリオンマ・レピジウム(Amblyomma
lepidium)
コイタマダニ属(Rhipicephalus)
クリイロコイタマダニ(Rhipicephalus
sanguineus)
リピセフアラス・アペンデイクラータス
(Rhipicephalus appendiculatus)
リピセフアラス・パルケラス(Rhipicephalus
pulchellus)
リピセフアラス・エベルチ(Rhipicephalus
everti)
ヒアロンマ属(Hyalomma)
ヒアロンマ・トランケイタム(Hyalomma
truncatum)
ヒアロンマ・ルフイペス(Hyalomma
rufipes)
ヒアロンマ・デトリタム(Hyalomma
detritum)
ヒアロンマ・マルギネイタム(Hyalomma
marginatum)
ヒアロンマ・ドロメダリイ(Hyalomma
dromedarii)
チマダニ属(Haemaphysalis)
フタトゲチマダニ(Haemaphysalis
longicornis)。
(2) ヒメダニ科(Argasidae)
カズキダニ属(Ornithodoros)
オルニソドロス・サビグニーイ
(Ornithodoros savignyi)
オルニソドロス・ラホレンシス
(Ornithodoros lahorensis)
オルニソドロス・トロザニ(Ornithodoros
tholozani)。
オトビウス属(Otobius)
オトビウス・メグニニ(Otobius megnini)
ヒセンダニ類として、
(1) ヒゼンダニ科(Sarcohtidae)
ヒゼンダニ(Sarcoptes scabiei)
シヨクヒヒゼンダニ(Chorioptes bovis)
(2) ニキビダニ科(Demodecidae)
イヌニキビダニ(Demodex canis)
(3) ワクモ科(Dermanyssidae)
ワクモ(Dermanyssus gallinae)
トリサシダニ(Ornithonyssus sylviarum)
シラミ類としては、
ニワトリオオハジラミ(Menacanthus
styamineus)
イヌハジラミ(Trichodectes canis)
ウシジラミ(Haematopinus eurysternus)
ブタジラミ(Haematopinus suis)
イヌジラミ(Linognathus setosus)
双翅目害虫としては、
(1) ウマバエ科(Gasterophilidae)
ウマバエ(Gasterophilus intestinalis)
(2) ヒツジバエ科(Oestridae)
ウシバエ(Hypoderma bovis)
キスジウシバエ(Hypoderma lineatum)
ヒツジバエ(Oestrus ovis)
(3) クロバエ科(Calliphoridae)
ルシリア・セリカータ(Lucilia sericata)
ラセンウジバエ(Cochliomyia hominivorax)
(4) ニクバエ科(Sarcophagidae)
サルコフアーガ・ハエマトデス(Sarcophaga
haematodes)
次に本発明の化合物の効果について、具体的に
試験例を挙げて説明する。但し、これのみに限定
されるものではない。
試験例1 フタトゲチマダニ(Haemaphysalis
eongicornis)に対する効果試験
アセトンを用いて、本発明化合物の1000ppm濃
度の溶液を作成し、コントロールとして、アセト
ンのみの溶液を作成した。試験容器は、ガラス管
ビン(径2.8cm、高さ10.5cm)を用い、その内側
に紙(これは円筒型で、内表面積142.9cm2、側
面130.6cm2、底と蓋24.6cm2)をセツトした。紙
は、あらかじめ上記の各種溶液に浸し、充分乾燥
させたものを用い、上記容器にセツトする。この
容器に幼ダニ20匹を放し、蓋(紙)をし、綿栓
でとめ、一定時間後に、各々ガラス管ビンより
紙を取り出し、実体双眼顕微鏡下で顕微鏡集光器
で光を放射し、体の移動、脚の可動をみて、体及
び脚を動かすものを生存しているものとして、生
死の判別をした。
なお、供試のダニは、単為生殖系の岡山株雌成
ダニ(フタトゲチマダニ)を家兎に吸血させ産卵
させ、その卵を孵化させた未吸血の幼ダニを用い
た。
試験の結果を第2表に示す。[Table] The application method for using the compound of the present invention to exterminate ectoparasites in animals is not particularly limited, but a local administration method is preferred. Local administration methods include, for example, directly sprinkling the powder containing the compound of the present invention or the compound of the present invention as it is on the animal, applying it partially or completely to the animal, or administering a powder containing the compound of the present invention in the form of a wettable powder or an emulsion. dilute with water,
By spraying or administering chemicals to the pool,
This method involves giving the animal a medicated bath. In the form of the pesticidal agent of the present invention, the compound of the present invention may be used as it is, or may be used together with appropriate auxiliaries such as carriers and additives.
The carriers and additives may be solid or liquid and include materials commonly used in pharmaceutical technology, such as natural substances, recycled substances, organic solvents and dispersants. Examples of solid carriers include clay, talc, bentonite, diatomaceous earth, etc., and examples of liquid carriers include water, alcohols (methanol, ethanol, etc.), aromatic hydrocarbons (benzene, toluene, etc.).
xylene, etc.), chlorinated hydrocarbons, ethers,
Examples include ketones, esters (ethyl acetate, etc.), acid amides (dimethylformamide, etc.), and if necessary, emulsifiers, dispersants, suspending agents, penetrating agents, spreading agents, stabilizers, etc. are added. However, it can be put to practical use in any form such as a solution, emulsion, wettable powder, powder, etc. By solution is meant, for example, the active ingredient in paraffin oil, corn oil or rapeseed oil for use in application methods. Furthermore, if necessary, a composition mixed with other veterinary drugs, synergists, etc. may be used during formulation or treatment. The amount of the compound of the present invention to be used varies depending on the condition of the animal to be treated, the species, the environment, and the desired result, but in general, it is diluted with water, for example, to reach an active ingredient concentration of 0.002. ~5% by weight (20~
50000ppm), especially 0.01~0.1% by weight (100~
It is preferable to use a dilute solution of 1000 ppm). Next, some specific formulation examples of the pesticidal agent of the present invention will be shown, but the invention is not limited to these. In addition, in the following formulation examples, "parts" mean parts by weight. Formulation Example 1 Emulsion Active ingredient (compound of the present invention) 50 parts Xylene 25 parts N,N-dimethylformamide 20 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Co., Ltd. )Product name) Mix the above ingredients uniformly to make an emulsion. Formulation example 2 Wettable powder Active ingredient (compound of the present invention) 25 parts Sieglite PFP 69 parts (kaolin clay: Sieglite Industries Co., Ltd. trade name) Solpol 5039 3 parts (nonionic surfactant and anionic surfactant) Mixture with agent: Toho Chemical Industries Co., Ltd. (trade name) Carplex (anti-caking agent) Mixture of 3-part surfactant and white carbon: Shionogi & Co., Ltd. (trade name) It is used as a Japanese medicine. Formulation Example 3 Powder Active ingredient (compound of the present invention) 3 parts Carplex (anti-caking agent) 0.5 part (mixture of surfactant and white carbon:
Shionogi & Co., Ltd. (trade name) Clay (produced in Gunma) 95 parts Diisopropyl phosphate 1.5 parts Mix and grind the above ingredients uniformly to make a powder. Next, examples of animal ectoparasites for which the compound of the present invention is highly effective include ticks, mites, lice, Diptera pests, Hemiptera pests, and the like.
Specific examples are given below. The ticks include (1) Ixodidae, Boophilus, Boophilus microplus, Boophilus microplus, and Boophilus microplus.
Boophilus decoloratus
annulatus) Amblyomma Amblyomma variegatum Amblyomma herbraeum Amblyomma
pomposum) Amblyomma americanum Amblyomma maculatum Amblyomma ziemma
gemma) Amblyomma lepidium (Amblyomma gemma)
lepidium) Rhipicephalus Rhipicephalus
sanguineus) Rhipicephalus appendiculatus Rhipicephalus appendiculatus Rhipicephalus parcellus
Rhipicephalus (Rhipicephalus)
everti) Hyalomma (Hyalomma) Hyalomma truncateum (Hyalomma
truncatum) Hyalomma rufuipes (Hyalomma truncatum)
rufipes) Hyalomma detritum (Hyalomma detritum)
detritum) Hyalomma marginatum (Hyalomma detritum)
marginatum) Hyalomma dromedaryi (Hyalomma dromedarii)
dromedarii) Haemaphysalis
longicornis). (2) Argasidae Genus Ornithodoros Ornithodoros savignyi Ornithodoros lahorensis Ornithodoros torozani
tholozani). Otobius (Otobius) Otobius megnini (1) Sarcoptes scabiei Chorioptes bovis (2) Demodecidae Demodex canis (3) Dermanyssidae Dermanyssus gallinae Ornithonyssus sylviarum Lice include Menacanthus
styamineus) Dog lice (Trichodectes canis) Cow lice (Haematopinus eurysternus) Pig lice (Haematopinus suis) Dog lice (Linognathus setosus) Diptera pests include: (1) Gasterophilidae Gasterophilus intestinalis (2) Oestridae Hypoderma bovis Hypoderma lineatum Oestrus ovis (3) Calliphoridae Lucilia sericata Cochliomyia hominivorax (4) Sarcophagidae Sarcophaga
haematodes) Next, the effects of the compounds of the present invention will be specifically explained by giving test examples. However, it is not limited to this only. Test Example 1 Haemaphysalis
Acetone was used to prepare a solution of the compound of the present invention at a concentration of 1000 ppm, and as a control, a solution containing only acetone was prepared. The test container used was a glass tube bottle (diameter 2.8 cm, height 10.5 cm) with paper (cylindrical shape, inner surface area 142.9 cm 2 , side surface 130.6 cm 2 , bottom and lid 24.6 cm 2 ) inside. It was set. Use paper that has been soaked in the various solutions mentioned above and dried thoroughly, and then set in the container. 20 young mites were released into this container, covered with a lid (paper), and secured with a cotton plug. After a certain period of time, the paper was removed from each glass tube bottle, and light was emitted using a microscope condenser under a stereoscopic binocular microscope. By looking at the movements of the body and legs, those who move their bodies and legs were considered to be alive, and we determined whether they were alive or dead. The test mite used was a parthenogenetic female adult mite of the Okayama strain (Ixodes vulgaris) that was sucked by a rabbit to lay eggs, and the eggs were hatched to form unfed young ticks. The test results are shown in Table 2.
【表】【table】
【表】【table】
Claims (1)
基を、R1,R2はそれぞれ独立に水素原子または
低級アルキル基を示し、R3はハロゲン原子、低
級アルキル基、シクロアルキル基、低級アルコキ
シ基、低級ハロアルキル基、低級ハロアルコキシ
基、シアノ基、トリメチルシリル基、ニトロ基、
【式】【式】 【式】【式】また は【式】(ただし、Xはハロゲン 原子、低級アルキル基、シクロアルキル基、低級
アルコキシ基、低級ハロアルキル基、低級ハロア
ルコキシ基、シアノ基またはニトロ基を、mは0
または1〜5の整数を示し、mが2〜5の場合は
Xは同一でも互いに異なつてもよい。)を示し、
nは0または1〜5の整数を示し、nが2〜5の
場合はR3は同一でも互いに異なつてもよい。R4
はハロゲン原子を示し、Zは酸素原子または硫黄
原子を示す。〕で表されるピリダジノン誘導体の
1種または2種以上を有効成分として含有する動
物用外部寄生虫駆除剤。 2 一般式()で表されるピリダジノン誘導体
において、Rが炭素数4の分岐を有するアルキル
基で、R4が塩素原子で、R1が水素原子である特
許請求の範囲第1項記載の動物の外部寄生虫駆除
剤。 3 外部寄生虫が家畜のダニ類である特許請求の
範囲第1項または第2項記載の動物の外部寄生虫
駆除剤。[Claims] 1 General formula (): [In the formula, R represents a linear or branched alkyl group, R 1 and R 2 each independently represent a hydrogen atom or a lower alkyl group, and R 3 is a halogen atom, lower alkyl group, cycloalkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, cyano group, trimethylsilyl group, nitro group,
[Formula] [Formula] [Formula] [Formula] or [Formula] (where X is a halogen atom, lower alkyl group, cycloalkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, cyano group, or nitro group , m is 0
Alternatively, it represents an integer of 1 to 5, and when m is 2 to 5, X may be the same or different. ),
n represents 0 or an integer of 1 to 5, and when n is 2 to 5, R 3 may be the same or different. R4
represents a halogen atom, and Z represents an oxygen atom or a sulfur atom. ] An animal ectoparasiticide containing one or more pyridazinone derivatives as an active ingredient. 2. The animal according to claim 1, wherein in the pyridazinone derivative represented by the general formula (), R is a branched alkyl group having 4 carbon atoms, R 4 is a chlorine atom, and R 1 is a hydrogen atom. ectoparasiticide. 3. The animal ectoparasiticide according to claim 1 or 2, wherein the ectoparasites are livestock mites.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16098983A JPS6054319A (en) | 1983-09-01 | 1983-09-01 | Repellant for external parasite of animal |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16098983A JPS6054319A (en) | 1983-09-01 | 1983-09-01 | Repellant for external parasite of animal |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6054319A JPS6054319A (en) | 1985-03-28 |
JPH0579647B2 true JPH0579647B2 (en) | 1993-11-04 |
Family
ID=15726454
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16098983A Granted JPS6054319A (en) | 1983-09-01 | 1983-09-01 | Repellant for external parasite of animal |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6054319A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07116161B2 (en) * | 1984-07-04 | 1995-12-13 | 日産化学工業株式会社 | Pyridazinone derivative |
EP0183212B1 (en) * | 1984-11-29 | 1990-06-20 | Nissan Chemical Industries Ltd. | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
-
1983
- 1983-09-01 JP JP16098983A patent/JPS6054319A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS6054319A (en) | 1985-03-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE69104071T2 (en) | Uracil derivatives and pesticides containing them as effective substances. | |
RU2037488C1 (en) | Derivatives of 3-cyano-5-alkoxy-1-arylpyrazole and composition on their basis | |
JP3250825B2 (en) | Substituted nitroguanidine derivatives, their production and insecticides | |
JP2583429B2 (en) | Imidazolines and insecticides | |
JPH07121909B2 (en) | Novel heterocyclic compound and insecticide | |
SK283823B6 (en) | Pesticidal 1-arylpyrazoles, method for their production, pesticidal composition containing them and use thereof | |
JPS62207266A (en) | Novel heterocyclic compound | |
BG61813B1 (en) | Pesticide 1-(2-pyridyl(pyrazoles), method for their preparation, pesticide formulations and methods for their usage for pest control | |
CZ286232B6 (en) | 1-Aryl-5-alkylideneiminopyrazole, process of its preparation pesticidal composition in which said pyrazole is comprised and method of fighting articulates, nematodes, flat- and roundworms and protozoa | |
JP2004359633A (en) | Utilization of isoindolinone derivative as insecticide | |
KR900000566B1 (en) | Photoactive azole pesticides | |
JPS63190880A (en) | Novel n-benzothiazolyl-amides and insecticide | |
JPS6033391B2 (en) | Novel phenylcarbamoyl-2-pyrazoline, its preparation process and arthropod killer compositions containing it as an active ingredient | |
JPH0579647B2 (en) | ||
JPS63159373A (en) | Pyridazinones and insecticide, acaricide and nematocide | |
JPH10168064A (en) | Insecticidal 1-arylpyrazole-5-sulfilimine derivative | |
JPS63159374A (en) | Pyridazinone derivative and insecticide, acaricide and nematocide | |
JP3711581B2 (en) | Semicarbazone derivatives and pest control agents | |
CA2009301A1 (en) | Pyrimidinetrione derivatives, processes for their preparation, agents containing them and their use as agents for combating pests | |
KR100289470B1 (en) | 2-(5-isoxazolinemethyloxyphenyl)-4,5,6,7-tetrahydro-2H-indazole derivatives with herbicidal activity | |
JPH0796481B2 (en) | Insecticide, acaricide | |
JPS63215673A (en) | Pyridazinone compound and controlling agent against disease and insect pest | |
JPH01224305A (en) | Anthelminthic of animal ectoprasite | |
JP2674102B2 (en) | Pyridazinone derivatives and pest control agents | |
JPH03176479A (en) | Quinoxalines and insect pest controlling agent |