JPS60255775A - Imidazole derivative and fungicide for non-medical purposes - Google Patents
Imidazole derivative and fungicide for non-medical purposesInfo
- Publication number
- JPS60255775A JPS60255775A JP59109824A JP10982484A JPS60255775A JP S60255775 A JPS60255775 A JP S60255775A JP 59109824 A JP59109824 A JP 59109824A JP 10982484 A JP10982484 A JP 10982484A JP S60255775 A JPS60255775 A JP S60255775A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- imidazole
- wood
- test
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002460 imidazoles Chemical class 0.000 title claims abstract description 9
- 239000000417 fungicide Substances 0.000 title abstract description 23
- 230000000855 fungicidal effect Effects 0.000 title abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 4
- 125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract 2
- 239000004480 active ingredient Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 239000000645 desinfectant Substances 0.000 claims description 2
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- 125000004429 atom Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 51
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract description 32
- 239000000463 material Substances 0.000 abstract description 3
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- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- BIWJNBZANLAXMG-YQELWRJZSA-N chloordaan Chemical compound ClC1=C(Cl)[C@@]2(Cl)C3CC(Cl)C(Cl)C3[C@]1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-YQELWRJZSA-N 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- 239000011035 citrine Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 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
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000010881 fly ash Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 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
- 229920005610 lignin Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000002424 termiticide Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- ZOKXUAHZSKEQSS-UHFFFAOYSA-N tribufos Chemical compound CCCCSP(=O)(SCCCC)SCCCC ZOKXUAHZSKEQSS-UHFFFAOYSA-N 0.000 description 1
- 238000010267 two-fold dilution method Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000003171 wood protecting agent Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は一般式(1)
(但し式中Rは炭素原子数1ないし8のアルキル基;シ
アノアルキル基;アルケニル基;)\ロアルケニル基;
アルキニル基:アルコキシアルキル基;アルコキシカル
ボニルアルキル基;アシルオキシアルキル基及びノ%ロ
ゲンfil子fit換されても良いフェノキシアルキル
基を示し、Xけ低級ハロアルキル基;低級アルコキシ基
;低級アルキルチオ基;低級ハロアA、 :I −e
シ基;低級ハロアルキルチオ基;アルケニルオキシ基;
アルキニルオキシ基;アルコキシカルボニル基;フェノ
キシ基及びベンジルオキシ基を示し、Yは同一でも異な
っても良く、水素原子;ノ・ロゲン原子;低級アルキル
基;低級アルコキシ基を示しnは1又は2の整数を示す
。又X及びYFi−緒になってアルキレンジオキシ基を
iわすこともできる。)
で表わされるイミダゾール誘導体、及び非医療用殺菌剤
に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the general formula (1) (wherein R is an alkyl group having 1 to 8 carbon atoms; a cyanoalkyl group; an alkenyl group;)\roalkenyl group;
Alkynyl group: alkoxyalkyl group; alkoxycarbonylalkyl group; acyloxyalkyl group and phenoxyalkyl group which may be substituted with X, lower haloalkyl group; lower alkoxy group; lower alkylthio group; lower halo A , :I-e
cy group; lower haloalkylthio group; alkenyloxy group;
Alkynyloxy group; alkoxycarbonyl group; phenoxy group and benzyloxy group, Y may be the same or different, hydrogen atom; shows. Moreover, X and YFi can also be used together to form an alkylenedioxy group. ) and non-medical disinfectants.
本発明者等は新規で有用な化合物を創出すべく研究を重
ねた結果一般式(1)で表わされるイミダゾール誘導体
が文献未記載の新規化合物であり、しかも該誘導体が農
業用殺菌剤及び木材防腐防カビ剤として有用であること
を見出し本発明を完成させたものである。又本発明のイ
ミダゾール誘導体には除草剤又は植物生長調節剤として
有用な化合物もある。As a result of repeated research to create new and useful compounds, the present inventors discovered that the imidazole derivative represented by the general formula (1) is a new compound that has not been described in the literature. The present invention was completed by discovering that it is useful as a fungicidal agent. The imidazole derivatives of the present invention also include compounds useful as herbicides or plant growth regulators.
本発明の一般弐山で表わされる化合物の製造方法として
は例えば下記に図示する方法を挙げることができる。Examples of the method for producing the compound represented by Nisan of the present invention include the method illustrated below.
(IV) (Ill)
+1)
(式中R,X、Y及びnは前記に同じ。)即ち一般式t
lV)で表わされる化合物とイミダゾールとを塩基の存
在下に反応させ一般式(IIIJで表わされる化合物と
し、さらに該化合物単離し、又は単離せずに一般式(1
1で表わされる化合物を塩基の存在下に反応させること
により一般式(1)で表わされるイミダゾール誘導体を
得ることができる。(IV) (Ill) +1) (In the formula, R, X, Y and n are the same as above.) That is, the general formula t
A compound represented by the general formula (IIIJ) is reacted with imidazole in the presence of a base, and the compound is then isolated or not isolated to form a compound represented by the general formula (1
The imidazole derivative represented by general formula (1) can be obtained by reacting the compound represented by 1 in the presence of a base.
本反応で使用できる溶媒としては本反応の進行を阻害し
ないものであれは艮く、ベンゼン、トルエン、キシレン
等の芳香族炭化水素類−四塩化炭素、塩化メチレン、り
aロホルム等の塩素化炭化水素類;酢酸エチル等のエス
テル類;アセトン、ジエチルケトン、メチルエチルケト
ン等のケトン類;ジエチルエーテル、テトラヒドロフラ
ン、ジオキサン等のエーテル類;又はこれらの混合物を
挙げることができる。Solvents that can be used in this reaction include those that do not inhibit the progress of this reaction, such as aromatic hydrocarbons such as benzene, toluene, and xylene, and chlorinated carbons such as carbon tetrachloride, methylene chloride, and lya-roform. Hydrogens; esters such as ethyl acetate; ketones such as acetone, diethyl ketone, and methyl ethyl ketone; ethers such as diethyl ether, tetrahydrofuran, and dioxane; and mixtures thereof.
反応温度は0℃乃至100℃の範囲から適宜選択される
。The reaction temperature is appropriately selected from the range of 0°C to 100°C.
塩基としてはトリメチルアミン、トリエチルアミン、ピ
リジン、ピコリン等の有機塩基類;水酸化ナトリウム、
水酸化カリウム、ナトリウムメチラート等の無機塩基又
はアルコラード等を使用することができる。Examples of bases include organic bases such as trimethylamine, triethylamine, pyridine, and picoline; sodium hydroxide;
Inorganic bases such as potassium hydroxide, sodium methylate, alcoholades, etc. can be used.
本反応は等モル反応であるので各々の試剤を等モル使用
すれば良いがいずれか一方の試剤を過剰に使用しても良
い。Since this reaction is an equimolar reaction, each reagent may be used in equimolar amounts, but one of the reagents may be used in excess.
B法 1ll (但し式中RXXXY及びnq前記に同じ。B method 1ll (However, in the formula, RXXXY and nq are the same as above.
Halはハロゲン原子を示す。)
即ち一般式(ロ)で表わされる化合物を適当な溶媒中で
塩基の存在下イミダゾールと反応させ一般式+vbで表
わされる化合物とし、該化合物を単離することなく一般
式(■で表わされる)・ライド類とを反応させることK
より一般式flJで表わされるイミダゾール誘導体を得
ることができる。Hal represents a halogen atom. ) That is, the compound represented by the general formula (b) is reacted with imidazole in the presence of a base in a suitable solvent to form a compound represented by the general formula +vb, and without isolating the compound, the compound represented by the general formula (represented by・Reacting with rides K
From this, an imidazole derivative represented by the general formula flJ can be obtained.
又一般式(至)で表わされる化合物にイミダゾール、一
般式tV)で表わされるノ・ライド類及び塩基とを同時
に添〃Oしても一般式(11で表わされるイミダゾール
類を得ることもできる。Further, imidazoles represented by the general formula (11) can also be obtained by simultaneously adding imidazole, a no-ride represented by the general formula tV), and a base to the compound represented by the general formula (tV).
本反応で使用できる溶媒としては本反応の進行を阻害し
ないものであれば良く、例えばメタノール、エタノール
、イソプロパツール等のアルコール類;ジメチルスルホ
ギシド、ジメチルホルムアミド、ヘキサメチレンホスホ
ロアミド、水等を挙げることができる。これらの溶媒は
単独でも使用されるが混合しても使用することができる
。Solvents that can be used in this reaction may be those that do not inhibit the progress of this reaction, such as alcohols such as methanol, ethanol, and isopropanol; dimethyl sulfogide, dimethyl formamide, hexamethylene phosphoramide, water, etc. can be mentioned. These solvents can be used alone or in combination.
本反応で使用できる塩基としては炭酸ナトリウム、炭酸
カリウム、炭酸水素ナトリウム、炭酸水素カリウム、水
酸化ナトリウム、水酸化カリウム等を挙げることができ
、これらは固体のオま使用することもできる。Examples of the base that can be used in this reaction include sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydroxide, and potassium hydroxide, and these can also be used in solid form.
反応温度は0乃至100℃の範囲から選択すれば良いが
特に室温附近で反応を行うのが好ましい。The reaction temperature may be selected from the range of 0 to 100°C, but it is particularly preferable to carry out the reaction around room temperature.
反応時間はO,S乃至24時間の範囲から適宜選択すれ
ば良い。The reaction time may be appropriately selected from the range of 0, S to 24 hours.
本反応に等モルであるので各試剤を等モル使用すれば艮
いがいずれかの試剤を過剰に使用しても良い。Since equimolar amounts are used in this reaction, it is possible to use an excess of any one of the reagents as long as equimolar amounts of each reagent are used.
又塩基の使用量も一般式(至)で表わされる化合物と等
モル又は若干過剰に使用すれば良い。Further, the amount of the base to be used may be equimolar to the compound represented by the general formula (2) or slightly in excess.
反応終了後反応液を常法どおり処理すれば良く、例えば
適当な溶媒で抽出分離し、更に再結晶又はカラムクロマ
トグラフィー法により精製することができる。After completion of the reaction, the reaction solution may be treated in a conventional manner, for example, extracted and separated with an appropriate solvent, and further purified by recrystallization or column chromatography.
一般式(1)で表わされる化合物の代表例を第1表に挙
げるが本発明はこれらに限定されるものではない。Representative examples of the compound represented by the general formula (1) are listed in Table 1, but the present invention is not limited thereto.
一般弐山 第 1 表 ? 以下に本発明の代表的な実施例を挙げる。General Niyama Table 1 ? Typical examples of the present invention are listed below.
区m例1 1−[1−(2−ジン口口メトキシフェニル
イミノ)−1−メチルチオメチルクー1H−イミタゾー
ルの合成(化合物番号6)2−シフ0ロメトキシフエニ
ルイソチオシアナート060り(α003モル)とイミ
ダゾールα20g (αθassモル)をジメチルホル
ムアミド15dlCWg解し、この溶液に粉末水酸化カ
リウムα22F(α0035モル)を加え攪拌下室源で
50分反応を行った。反応後更にヨウ化メチルα64F
(0,0045モル)を滴下し55時間室温で反応を行
った。反応終了後、反応液に多量の水を加え、目的物を
酢酸エチルで抽出した。Example 1 Synthesis of 1-[1-(2-Methoxyphenylimino)-1-methylthiomethyl-1H-imitazole (Compound No. 6) 2-Shiflomethoxyphenylisothiocyanate 060 (α003 mol) and imidazole α (αθass mol) were dissolved in 15 dlCWg of dimethylformamide, powdered potassium hydroxide α22F (α0035 mol) was added to this solution, and the reaction was carried out in a room under stirring for 50 minutes. After the reaction, methyl iodide α64F
(0,0045 mol) was added dropwise and the reaction was carried out at room temperature for 55 hours. After the reaction was completed, a large amount of water was added to the reaction solution, and the target product was extracted with ethyl acetate.
抽出液を水洗した後無水硫酸マグネシウムで乾燥後溶媒
を留去して油状物を得た。得られた油状物をシリカゲル
クロマトグラフィーによって精製し目的物を油状物とし
てα46y得た。The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain an oil. The obtained oil was purified by silica gel chromatography to obtain the desired product α46y as an oil.
nド15800 収率 54.1%
NMRδ値(TMS/CC14) ppm2.3y (
B、5H)、640(t、IH)、&4〜z5(m、6
H)、7.70(s、IH)
実施例2 1−[1−(2,4−ジクロロ−5−イソプ
ロポキシフェニルイミノ)−1−イソプロピルチオメチ
ル)−1H−イミダゾールの合成(化合物番号12)
2.4−ジクロロ−5−イソプロポキシフェニルインチ
オシアナートαBay (α0053モル)、イミダゾ
ールα28jE (α004モル)をジメチルスルホキ
シド10sdに溶解し、水酸化ナトリウム粉末α15f
([10037モル)を加えて室温で1時間攪拌反応
させた。この反応混合物に沃化イソプロピルα6y(α
0055モル)を室温下で加えさらに2時間反応を行な
った。反応混合物に水を加えて酢酸エチルで抽出し、酢
酸エチル層は水洗後無水硫酸ナトリウムで脱水してから
濃縮した。得られた粗生成物はシリカゲルカラムクロマ
トグラフィーによって精製した。ndo 15800 Yield 54.1% NMR δ value (TMS/CC14) ppm2.3y (
B, 5H), 640 (t, IH), &4~z5 (m, 6
H), 7.70 (s, IH) Example 2 Synthesis of 1-[1-(2,4-dichloro-5-isopropoxyphenylimino)-1-isopropylthiomethyl)-1H-imidazole (Compound No. 12 ) 2.4-dichloro-5-isopropoxyphenylinthiocyanate αBay (α0053 mol) and imidazole α28jE (α004 mol) were dissolved in dimethyl sulfoxide 10sd, and sodium hydroxide powder α15f was dissolved.
([10037 mol)] was added, and the mixture was stirred and reacted at room temperature for 1 hour. Isopropyl iodide α6y (α
0055 mol) was added at room temperature, and the reaction was further carried out for 2 hours. Water was added to the reaction mixture and extracted with ethyl acetate, and the ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated. The obtained crude product was purified by silica gel column chromatography.
nテ 1.5952 収率 51%
NMRδ値 (7MS/CCl4) ppm1.27
(d、 6)1)、1.52(d、6H)、it5(m
。nte 1.5952 Yield 51% NMR δ value (7MS/CCl4) ppm 1.27
(d, 6) 1), 1.52 (d, 6H), it5 (m
.
IH)、4.42(m、IB)、&45〜a08(m、
5H)実施例3 1−(1−(5−りaロー2−イソプ
ロポキシフェニルイミノ)−1−(シアノメチルチオ)
メチル)−1H−イミダゾールの合成(化合物第号59
)
5−クロロ−2−イソプロポキシフェニルインチオシア
ナート(L6BjF (α003モル)とイミダゾール
α22F(α0053モル)をジメチルホルムアミド1
511tに溶解し、さらに水酸化カリウム粉末o、zz
p (α0033モル)を加え室温で1時間攪拌した。IH), 4.42 (m, IB), &45~a08 (m,
5H) Example 3 1-(1-(5-ria-2-isopropoxyphenylimino)-1-(cyanomethylthio)
Synthesis of methyl)-1H-imidazole (Compound No. 59
) 5-chloro-2-isopropoxyphenylinthiocyanate (L6BjF (α003 mol) and imidazole α22F (α0053 mol) were dissolved in dimethylformamide 1
511t and further potassium hydroxide powder o, zz
p (α0033 mol) was added and stirred at room temperature for 1 hour.
その後クロルアセトニトリルα27P(α0036モル
)を水冷下部下し、室温で4時間攪拌した。そして、実
施例1と同様に処理、精製して、目的物α78りを得た
。Thereafter, chloroacetonitrile α27P (α0036 mol) was added to the mixture under water cooling, and the mixture was stirred at room temperature for 4 hours. Then, the product was treated and purified in the same manner as in Example 1 to obtain the target product α78.
n 1.5873 収率 7&Oチ
NMRδ値(TMS/CCIa ) I)Pm1.11
(d、6H)、5.80(s、2H)、4.26(m
。n 1.5873 Yield 7&OtiNMRδ value (TMS/CCIa) I) Pm1.11
(d, 6H), 5.80 (s, 2H), 4.26 (m
.
18)、6.5〜7.1 (m、5H)、7.55(s
、IH1実施例4 1−(1−アリルチオ−1−(2−
イングロボキシフiニルイミノ)メチル〕−1H−イミ
ダゾールの合成(化合物番号43)9−インプロポキシ
フェニルインチオシアナート2.32F(α012IR
1)とイミダゾールα90y(10152モル) をジ
メチルホルムアミド301KM解し、さらに水酸化カリ
ウム粉末cL87j+(10132モル)を加え室温で
1時間攪拌した。18), 6.5-7.1 (m, 5H), 7.55 (s
, IH1 Example 4 1-(1-allylthio-1-(2-
Synthesis of ingloboxifinylimino)methyl]-1H-imidazole (compound number 43) 9-inpropoxyphenylinthiocyanate 2.32F (α012IR
1) and imidazole α90y (10,152 mol) were dissolved in 301 KM of dimethylformamide, potassium hydroxide powder cL87j+ (10,132 mol) was added, and the mixture was stirred at room temperature for 1 hour.
その後アリルブロマイド1.74F (0,0144モ
ル)を滴下し室温下4時間攪拌した。多量の水を加え、
酢酸エチルで抽出し、水で3回洗浄し、無水硫酸マグネ
シウムで乾燥したのち、酢酸エチルを留去して、油状物
を得た。これをシリカゲルカラムクロマトグラフィーに
よって精製し、目的物!h55Fを得た。Thereafter, 1.74 F (0,0144 mol) of allyl bromide was added dropwise and stirred at room temperature for 4 hours. Add lots of water,
After extraction with ethyl acetate, washing three times with water, and drying over anhydrous magnesium sulfate, ethyl acetate was distilled off to obtain an oil. This was purified by silica gel column chromatography and the desired product was obtained! h55F was obtained.
ル
np i−5640収率 92.0%
NMRδ値(7MS/CCl4) ppm1.20(d
、 6H)、3.4s(d、2H)、4.35(m。np i-5640 yield 92.0% NMR δ value (7MS/CCl4) ppm1.20 (d
, 6H), 3.4s (d, 2H), 4.35 (m.
11()、a、a 〜5.3(m、 2H)、5.4〜
6.2(m、 IH)、6.6−7.5 (m、 6H
)、7.75(s、IH)実施例5 1−(1アリルチ
オ−1−(2−(2−グロビニルオキシ)フェニルイミ
ノ)メチル〕−1H−イミダゾールの合成(化合物番号
52)
2− (2−フロビニルオキシ)フτニルイソチオシア
ナー)0.95jE(α005モル)とイミダゾールl
14151(α006モル)ヲジメチルスルホキシド1
5Mに溶解し、さらに水酸化カリウム粉末0.569
(α0055モル)を加え室温で50分攪拌した。その
後アリルブロマイド0.915E(α0075モル)を
滴下し室温で4時間攪拌した。11 (), a, a ~5.3 (m, 2H), 5.4 ~
6.2 (m, IH), 6.6-7.5 (m, 6H
), 7.75(s, IH) Example 5 Synthesis of 1-(1allylthio-1-(2-(2-glovinyloxy)phenylimino)methyl]-1H-imidazole (Compound No. 52) 2-( 0.95jE (α005 mol) and imidazole l
14151 (α006 mol) Odimethyl sulfoxide 1
Dissolved in 5M and further added potassium hydroxide powder 0.569
(α0055 mol) was added and stirred at room temperature for 50 minutes. Thereafter, 0.915E (α0075 mol) of allyl bromide was added dropwise and stirred at room temperature for 4 hours.
セして、実施例1と同様に処理、精製して目的物119
りを得た。The target product 119 was treated and purified in the same manner as in Example 1.
I got it.
nD 1.6Q80 収率 79.9%本発明化合物は
以下に示す如く、非医療用殺菌剤として有用で、例えば
植物の保験剤としてまた木材、木質加工物の保護剤とし
てとシわけ有用であり、本発明の範囲に槁する。nD 1.6Q80 Yield 79.9% As shown below, the compound of the present invention is useful as a non-medical fungicide, for example, as a preservative for plants and as a protectant for wood and wood products. Yes, within the scope of the present invention.
本発明化合物は農園芸用殺菌剤として有用である。例え
ば郡イモチ病(Piricularia oryzae
);大麦、小麦のウトンコ病(Erysiphe gr
aminis )並びにキュウリのウドノコ病(Sph
aerothecafulginea l、リンゴのウ
ドノコ病(PodosphaeraIeucotric
ba l 及びブドウのウドノコ病[Jncinula
necator )等の種々の宿主植物についてのウ
ドンコ病;小麦のサビ病(Pucciniav6con
dita ) :エンバクの冠サビ病(Pucc 1n
iacoronate )及び他の宿主植物のサビ病;
トマトの灰色疫病(Phytophthora cap
sici )及び他の宿主植物の疫病;キュウリの灰色
カビ病等の病害、及び芝のさび病(Puccinia
spp、 ) 7ラウンパンチ(Rh1zoctoni
a 5olani K11hn )等の病害の防除の防
除にきわめて有効である。又本発明化合物は例えば水稲
、麦の倒伏防止、芝の生育抑制等の植物生長調節剤とし
ても有用である。The compounds of the present invention are useful as agricultural and horticultural fungicides. For example, Piricularia oryzae
); downy mildew of barley and wheat (Erysiphe gr
aminis) and cucumber powdery mildew (Sph
aerothecafulgineal, apple powdery mildew (PodosphaeraIeucotric)
ba l and powdery mildew of grapes [Jncinula
powdery mildew on various host plants such as P. necator; wheat rust (Pucciniav6con);
dita): Oat crown rust (Pucc 1n
iacoronate ) and other rust diseases of host plants;
Gray late blight of tomatoes (Phytophthora cap)
sici) and other host plant diseases; diseases such as botrytis blight of cucumbers, and turf rust (Puccinia
spp, ) 7 round punch (Rh1zoctoni
It is extremely effective in controlling diseases such as A. a.5olani.K11hn). The compounds of the present invention are also useful as plant growth regulators, for example, for preventing the lodging of paddy rice and wheat, and for suppressing the growth of grass.
又本発明化合物は木材防腐防カビ剤としても有用である
。The compounds of the present invention are also useful as wood preservatives and fungicides.
木材を腐朽させたり、汚染して製品の価(iFiを著し
く低下させる菌は木材の伐採から製材加工し最終製品の
段階に至る寸で種々の条件によって発生する。例えば木
材を腐朽させる菌としてはカワラタケ(Coriolu
s versicolor ) 、ヒイロタケ(Pyc
noporus coccineus )、ポシゲタヶ
(Asterostroma apalum )等の白
色腐朽菌:イドタケ(Coniophora pute
ana )、ナミダタケ(Serpula Iacry
mans ) 、オオウズラタケfTyromyces
palustria )等の褐色腐朽菌;ケトミウム
フロボーサム(Chaetomium globos
um )等の軟腐朽菌;木材の表面を汚染する菌として
はベニシリヌム シトリラム(Penicillium
citrinum ) 、アスペルギルス ニガー(A
sper−g目1us niger )、トリコデルマ
ビリディ(Trichoderma viridea
)等の子嚢菌類に対して有効である。又本発明化合物
は立木を侵す菌に対しても有効である。Bacteria that rot or contaminate wood and significantly reduce the value of the product (iFi) occur under various conditions during the stages from logging to sawing to final products.For example, fungi that rot wood include Coriolu
s versicolor), Pyc
White rot fungi such as Coniophora pute (Noporus coccineus) and Asterostroma apalum.
ana), Serpula Iacry
mans), Tyromyces fTyromyces
brown rot fungi such as Chaetomium globos (Palustria); Chaetomium globos
Soft-rotting fungi such as Benicillium um); fungi that contaminate wood surfaces include Penicillium
citrinum), Aspergillus niger (A
super-g order 1us niger), Trichoderma viridea (Trichoderma viridea)
) and other ascomycetes. The compounds of the present invention are also effective against fungi that attack standing trees.
本発明化合物を有効成分として農園芸用殺菌剤として使
用する場合、農薬製剤上の常法により、使用に都合のよ
い剤型に調製される。例えば粉剤、粒剤、微粒剤、水利
剤、乳剤、油剤、エアゾール、フローダスト、燻煙剤、
蒸散剤、錠剤等の形に補助剤と共に混合して調製され、
野菜、花弁、特用作物、果樹、樹木類等の茎葉部にその
寸ま、又は水で適量に希釈して適用される。本発明にお
いて、有効成分の適用量は、化合物の種類、対象、使用
方法等によって必ずしも一定しないが、有効成分として
10アール当り5〜500yの範囲から選ぶことができ
る。When the compound of the present invention is used as an agricultural and horticultural fungicide as an active ingredient, it is prepared into a dosage form convenient for use by conventional methods for agricultural chemical formulations. For example, powders, granules, fine granules, irrigation agents, emulsions, oils, aerosols, flow dust, smoke agents,
It is prepared by mixing with adjuvants in the form of transpiration agents, tablets, etc.
It can be applied to the stems and leaves of vegetables, flower petals, specialty crops, fruit trees, trees, etc., or diluted with an appropriate amount of water. In the present invention, the amount of the active ingredient to be applied is not necessarily constant depending on the type of compound, target, method of use, etc., but can be selected from the range of 5 to 500 Y per 10 A of the active ingredient.
本発明薬剤は、それが適用される時に同様に使用されう
る農薬、肥料、植物栄養素等と混合組成して又は併用し
て使用することもできる。The agent of the present invention can also be used in a mixed composition or in combination with agricultural chemicals, fertilizers, plant nutrients, etc. that can be used in the same way when the agent is applied.
例えば本発明化合物を有効成分とする農園芸用殺菌剤を
もって病害を防除する場合、この病害の発生と時期を同
じくする他の病害虫の防除剤を混合することによって多
目的防除剤とすることもできる。For example, when a disease is controlled using an agricultural and horticultural fungicide containing the compound of the present invention as an active ingredient, it can be made into a multipurpose control agent by mixing it with a control agent for other pests that occur at the same time as the disease outbreak.
又本発明化合物を木材防腐防カビ剤として使用する場合
、常法により、使用に都合のよい剤型に調製すれは艮く
、例えば油剤、乳剤、液剤、水和剤、粉剤、粒剤、塗料
等の形に補助剤と共に調製され、伐採後、最終製品に至
る各段階の木材及び家屋の土台、外壁回り、浴室、台j
lr、屋根等(二処理される。又立木等に寄生し、樹幹
や枝を変質枯死させる菌類に対しても茎葉又は根部上1
11に処理することができる。In addition, when the compound of the present invention is used as a wood preservative and fungicidal agent, it may be prepared in a form convenient for use by conventional methods, such as oil, emulsion, liquid, wettable powder, powder, granule, or paint. It is prepared with auxiliary agents in the form of wood, etc., and after felling, it is used at each stage until the final product, as well as the foundations of houses, around external walls, bathrooms, and stands.
lr, roofs, etc. (2 treatments. Also, for fungi that parasitize standing trees, etc. and cause deterioration and death of tree trunks and branches, 1
11.
有効成分の配合割合は必要に応じて加減し得る。例えば
粉剤、粒剤或は油剤の場合通常α1〜20%(重量部)
、又乳剤或いは水和剤の場合10〜50%(重量部)が
適当である。The blending ratio of active ingredients can be adjusted as necessary. For example, in the case of powders, granules, or oils, α is usually 1 to 20% (parts by weight).
In the case of emulsions or wettable powders, 10 to 50% (parts by weight) is suitable.
処理方法は公知の防腐防カビ剤の処理方法を適用すれば
良く、例えば伐採後の木材及び木材の加工時に薬剤を塗
布、噴霧、散布、浸漬等の常圧での処理、加圧注入法、
減圧処理法、拡散法又は合板やパーティクルボードに於
ける接着削混入法、家屋においては保護すべき木質部分
やカビの発生する場所例えば床下、壁面等に吹付は処理
、塗布処理、穿孔処理又は泡沫散布処理等が可能である
。又これらの処理方法を併用することにより一層確実な
効果が期待できるものである。As for the treatment method, it is sufficient to apply a known treatment method for a preservative and fungicidal agent, such as applying a chemical during the processing of wood and wood after felling, treatment under normal pressure such as spraying, scattering, and dipping, pressurized injection method,
Decompression treatment method, diffusion method, adhesion mixing method for plywood or particle board, spraying treatment, coating treatment, perforation treatment, or foam treatment on wooden parts that need to be protected and places where mold occurs in houses, such as under floors, walls, etc. Spraying treatment, etc. is possible. Moreover, even more reliable effects can be expected by using these treatment methods in combination.
有効成分の適用量は必ずしも一定しないが有効成分とし
て木材1イ当りα1ノ乃至5y又は木材1−当りαI
Kg乃至10KPの範囲から適宜選択すれば良い。The amount of the active ingredient applied is not necessarily constant, but the active ingredient may be α1 to 5y per 1 piece of wood or αI per 1 piece of wood.
It may be selected appropriately from the range of Kg to 10KP.
本発明化合物を農園芸用殺菌剤及び防腐防カビ剤として
使用するために製剤する場合、不活性担体及び必要に応
じて補助剤等と共に製剤化すれば良く、例えば本発明で
使用できる不活性担体としては固体、液体のいずれであ
ってもよく、固体の担体となりうる材料としては、例え
ばダイズ粉、穀物粉、木粉、樹皮粉、鋸粉、タバコ茎粉
、クルミ穀粉、ふすま、繊維素粉末、植物エキス抽出後
の残渣等の植物性粉末;紙、ダンボール類、ふるぎれ等
の繊維製品;粉砕合成樹脂等の合成重合体;粘土類(例
えばカオリン、ベントナイト、酸性白土)、タルク類(
例えばタルク、ヒロフイライト)、シリカ類(例えば珪
藻土、砕砂、雲母、ホワイトカーボン〔含水微粉硅素、
含水硅酸ともいわれる合成高分散硅酸で、製品により硅
酸カルシウムを主成分として含むものもある〕)、活性
炭、イオウ粉末、軽石、焼成硅藻土、レンガ粉砕物、フ
ライアッシュ、砂、炭酸カルシウム、燐酌カルシウム等
の無機鉱物性粉末;硫安、燐安、硝安、尿素、塩安等の
化学肥料、堆肥等を挙げることができる。これらは単独
で若しくは2種以上の混合物の形で使用される。液体の
担体となシうる材料としては、それ自体溶媒能を有する
もののほか、溶媒能を有さすとも補助剤の助けKより有
効成分化合物を分散させうろこととなるものから選ばれ
、例えば次のものがあるが、これらは単独で若しくF′
i2種以上の混合物の形で使用される;水、アルコール
類(例えばメタノール、エタノール、イングロバノール
、ブタノール、エチレングライコール)、ケトンa(例
えばアセトン、メチルエチルケトン、メチルイソブチル
ケトン、ジイソブチルケトン、シクロヘキサノン)、エ
ーテル類(例えばエチルエーテル、ジオキサン、セロソ
ルブ、シクロビルエーテル、テトラハイドロフラン)、
脂肪族炭化水素類(例えばガソリン、ケロシン、鉱油)
、芳香族炭化水素類(例えばベンゼン、トルエン、キシ
レン、ソルベントナフサ、アルキルナフタレン)、ハロ
ゲン化炭化水素類(例えばジクロロエタン、塩素化ベン
ゼン、クロロポルム、四塩化炭素)、エステル類(例え
ば酢酸エチル、ジブチルツクレート、ジイソプロピルフ
タレート、ジオクチルフタレート)、酸アミド類(例え
ばジメチルホルムアミド、ジエチルホルムアミド、ジメ
チルアセタマイド)、ニトリル類(例えばアセトニトリ
ル)、ジメチルスルホキサイド等。When formulating the compound of the present invention for use as an agricultural and horticultural fungicide and antiseptic fungicide, it may be formulated together with an inert carrier and, if necessary, an auxiliary agent, etc. For example, an inert carrier that can be used in the present invention The carrier may be either solid or liquid, and examples of materials that can serve as solid carriers include soybean flour, grain flour, wood flour, bark powder, saw flour, tobacco stem flour, walnut flour, bran, and cellulose powder. , plant powders such as residues after extracting plant extracts; textile products such as paper, cardboard, and furugiri; synthetic polymers such as crushed synthetic resins; clays (e.g. kaolin, bentonite, acid clay), talc (
For example, talc, hyrofluorite), silicas (for example, diatomaceous earth, crushed sand, mica, white carbon [hydrous fine powder silicon,
Synthetic highly dispersed silicic acid, also called hydrated silicic acid; some products contain calcium silicate as a main component]), activated carbon, sulfur powder, pumice, calcined diatomaceous earth, crushed bricks, fly ash, sand, carbonic acid. Examples include inorganic mineral powders such as calcium and phosphorous-diluted calcium; chemical fertilizers such as ammonium sulfate, ammonium phosphorus, ammonium nitrate, urea, and ammonium chloride; compost; and the like. These may be used alone or in the form of a mixture of two or more. Materials that can serve as liquid carriers are selected from those that themselves have solvent ability, as well as those that have solvent ability but can disperse the active ingredient compound with the help of adjuvants, such as the following: There are some things, but these can be used alone or as F'
iUsed in the form of a mixture of two or more; water, alcohols (e.g. methanol, ethanol, inglobanol, butanol, ethylene glycol), ketones a (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone), ethers (e.g. ethyl ether, dioxane, cellosolve, cyclobyl ether, tetrahydrofuran),
Aliphatic hydrocarbons (e.g. gasoline, kerosene, mineral oil)
, aromatic hydrocarbons (e.g. benzene, toluene, xylene, solvent naphtha, alkylnaphthalene), halogenated hydrocarbons (e.g. dichloroethane, chlorinated benzene, chloroporum, carbon tetrachloride), esters (e.g. ethyl acetate, dibutyl chloride), acid amides (e.g. dimethylformamide, diethylformamide, dimethylacetamide), nitriles (e.g. acetonitrile), dimethyl sulfoxide, etc.
補助剤としては次のものを挙げることができる。The following may be mentioned as adjuvants.
これらの補助剤は目的に応じて使用される。These adjuvants are used depending on the purpose.
ある場合には2種以上の補助剤を併用する。またある場
合には、全く補助剤を使用しないこともある。有効成分
化合物の乳化、分散、可溶化または及び湿潤の目的のた
めに界面活性剤が使用される。例えば次のものが挙げら
れる:ポリオキシエチレン、アルキルアリールエーテル
、ポリオキシエチレン、アルキルエーテル、ポリオキシ
エチレン、高級脂肪酸エステル、ポリオキシエチレン、
樹脂酸エステル、ポリオキシエチレン、ゾルビタンモノ
ラウレート、ポリオキジエチレン、ソルビタンモノオレ
エート、アルキルアリール、スルホン酸塩、ナフタレン
スルホン酸縮合物、フグニンスルホン酸塩、高級アルコ
ール(j!酸エステル等、有効成分化合物の分散安定化
、粘着または及び結合の目的のために例えば次のものを
使用することもよい:カゼイン、ゼラチン、でん粉、ア
ルギン酸、メチルセルロース、カルボキシメチルセルロ
ース、アラビアゴム、ポリビニルアルコール、松根油、
糠油、ベントナイト、リグニンスルホン[1゜固体製品
の流動性改良の目的のために次のものを使用することも
よい:ワックス等、ステアリン醸塩、燐酸アルキルエス
テル等。In some cases, two or more adjuvants are used together. In other cases, no adjuvant may be used at all. Surfactants are used for the purpose of emulsifying, dispersing, solubilizing or wetting the active ingredient compounds. Examples include: polyoxyethylene, alkylaryl ether, polyoxyethylene, alkyl ether, polyoxyethylene, higher fatty acid ester, polyoxyethylene,
Resin acid ester, polyoxyethylene, sorbitan monolaurate, polyoxyethylene, sorbitan monooleate, alkylaryl, sulfonate, naphthalene sulfonic acid condensate, fugunin sulfonate, higher alcohol (j! acid ester, etc.) For the purpose of dispersion stabilization, adhesion or binding of the active ingredient compounds, the following may be used, for example: casein, gelatin, starch, alginic acid, methylcellulose, carboxymethylcellulose, gum arabic, polyvinyl alcohol, pine oil. ,
Bran oil, bentonite, lignin sulfone [1° The following may also be used for the purpose of improving the fluidity of solid products: wax, etc., stearin salt, phosphoric acid alkyl ester, etc.
懸濁性製品の解こう剤として次のものを使用することも
よい:ナフタレンスルホン酸縮合物、縮合燐酸塩等。The following may also be used as peptizers for suspendable products: naphthalene sulfonic acid condensates, condensed phosphates, etc.
消泡剤例えばシリコン油等を添加することも可能である
。It is also possible to add antifoaming agents such as silicone oil.
本発明化合物を農園芸用殺菌剤又は防腐防カビ剤として
使用する場合、それらが適用される時に同時に使用され
うる殺菌剤、殺虫剤、防腐剤、防カビ剤、防蟻剤、防虫
剤等と混合組成して又は併用して使用することもできる
。When the compounds of the present invention are used as agricultural and horticultural fungicides or preservatives and fungicides, they may be used simultaneously with fungicides, insecticides, preservatives, fungicides, termiticides, insect repellents, etc. They can also be used in a mixed composition or in combination.
例えば木材防汚防カビ剤として使用する場合、これと併
用できる活性成分としては例えばTBTO(ビストリブ
チルスズオキサイド)、TBTP()リプチルスズフタ
レート)等の有機スズ系殺菌剤;フルトラニル(2−ト
リフルオロメチル−57−インプロポキシベンズアニリ
ド、メプロニル(2−メチル−51−インプロポキシベ
ンズアニリド等の酸アニリド系殺菌剤;クレオンート油
、ナンテン酸金属塩、IF−1000(4−クロルフェ
ニル−5−ヨートグロバルギルホルマール)、キシラサ
ンーAim(N−ニトロソ−シクロへキシルヒドロオキ
シルアミン−アルミニウム塩)、ジクロフルアニド(N
−ジクロロフルオロメチk f :# −N’、N’
−’) )’ チル−N−フェニルスルファミド)等の
防腐防カビ剤;
クロルデン、クロルピリホス、ピリダフェンチオン、プ
ロチオホス、カルボスルフアン及ヒバ−メスリン等の殺
蟻剤を挙げることができる。For example, when used as a wood stain and fungicide, active ingredients that can be used in combination include organotin fungicides such as TBTO (bistributyltin oxide) and TBTP (liptyltin phthalate); Acid anilide fungicides such as methyl-57-impropoxybenzanilide, mepronil (2-methyl-51-impropoxybenzanilide); creonate oil, metal salts of nanthenate, IF-1000 (4-chlorophenyl-5-iotoglobal gil formal), xylasan-Aim (N-nitroso-cyclohexylhydroxylamine-aluminum salt), dichlorofluanid (N
-dichlorofluoromethi k f :# -N', N'
Preservatives and fungicides such as chlordane, chlorpyrifos, pyridafenthione, prothiophos, carbosulfan and hibermethrin can be mentioned.
又農園芸用殺菌剤として使用する場合、この病害の発生
と時期を同じくする他の病害虫の防除剤を混合すること
によって多目的防除剤とすることもできる。例えばアセ
フェート、アルフェート、マラソy、MEP、BPMC
,MTMC。When used as a fungicide for agriculture and horticulture, it can also be used as a multipurpose pest control agent by mixing it with a control agent for other pests that occur at the same time as the disease outbreak. For example, acephate, alpha, marasoy, MEP, BPMC
, MTMC.
ブプロフェジン等の殺虫剤、EDDP、IBP、イソブ
ロチオラン等の殺菌剤を挙けることができる。Insecticides such as buprofezin, fungicides such as EDDP, IBP, and isobrothiolane can be mentioned.
以下に本発明の代表的な試験例及び処方例を挙げるが本
発明はこれらに限定されるものではない。伺処方例中、
部とあるのは重量部を示す。Typical test examples and formulation examples of the present invention are listed below, but the present invention is not limited thereto. In the prescription example,
Parts indicate parts by weight.
試験例1 大麦ウドノコ病の治療効果試験直径12c+
++の磁性ポストに栽培した大麦(品種関東6号、2葉
期)にウドンコ病菌
fErysiphe graminis F、 sp、
hordei )をふりかけ接種し、1日後に有効成
分として本発明化合物を含む薬剤を所定濃度に希釈し、
スプレーガンを使用してターンテーブル上で散布した。Test Example 1 Treatment effect test for barley powdery mildew Diameter 12c+
Powdery mildew fungus fErysiphe graminis F, sp,
hordei), and one day later, a drug containing the compound of the present invention as an active ingredient was diluted to a predetermined concentration,
Spraying was done using a spray gun on a turntable.
散布後25℃の温室に保管し、接1117日後に無処理
区と比較してそれぞれの防除効果を調査した。After spraying, the plants were stored in a greenhouse at 25°C, and 1,117 days after application, the pesticidal effects of each were investigated in comparison with the untreated plot.
判定は下記の基準による。Judgment is based on the following criteria.
4:防除価 100〜95% 5:a 94〜80% 2 〃 79〜60% 1:# 59〜0% 結果を第2表に示す。4: Control value 100-95% 5:a 94-80% 2〃〃〃〃79~60% 1:# 59-0% The results are shown in Table 2.
試験例2 稲イモチ病防除効果
直径9cmの禦焼鉢に植えたS(品種;日本晴、5葉期
、10本植え)に本発明化合物を有効成分とする薬剤の
所定濃度に調製した薬液をスプレーガンで充分に散布し
、散布1日後に稲イモチ病菌(Pyricularja
oryzae )の胞子懸濁液を噴霧接種した。温室
に20時間置い友後、温室に移し、接種6日後に病斑数
を調査し無処理区と比較して防除価を算出し、試験例1
と同じ基準で効果の判定を行った。Test Example 2 Effect on rice blast disease control S (variety: Nipponbare, 5-leaf stage, 10 plants planted) planted in a pottery pot with a diameter of 9 cm was sprayed with a chemical solution prepared at a predetermined concentration containing the compound of the present invention as an active ingredient. One day after spraying, the rice rootworm disease fungus (Pyricularja) was sprayed thoroughly.
oryzae) was inoculated by spraying. After leaving it in the greenhouse for 20 hours, it was transferred to the greenhouse, and 6 days after inoculation, the number of lesions was investigated and the control value was calculated by comparing it with the untreated area. Test Example 1
The effectiveness was judged using the same criteria.
結果を第3表に示す。The results are shown in Table 3.
第 5 表
試験例3 稲ごま葉枯病防除試験
素焼鉢(+74径91M)に植えた5葉期のfIFif
品種8日品種8ラ
た薬液をスプレーガンで十分に散布し、1日後にごま葉
枯病菌(Cochliobolus myabeanu
s )の胞子懸濁液を噴霧接種した。温室に20時間置
いた後、温室に移し接種6日後に一葉づつの病斑数を調
査し防除率を新出した。試験例1と同じ基準で効果の判
定を行った。−区5連制結果を第4表に示す。Table 5 Test Example 3 Rice sesame leaf blight control test fIFif at the 5-leaf stage planted in a clay pot (+74 diameter 91M)
Variety 8 Days Variety 8 RatsA chemical solution was sufficiently sprayed with a spray gun, and after 1 day, the sesame leaf blight fungus (Cochliobolus myabeanu) was detected.
The spore suspension of s) was inoculated by spraying. After being placed in a greenhouse for 20 hours, the seeds were transferred to a greenhouse, and 6 days after inoculation, the number of lesions on each leaf was counted to determine the control rate. The effectiveness was evaluated using the same criteria as Test Example 1. -Table 4 shows the results of the 5 consecutive wards.
第 4 表
試験例4: 燕麦の冠さび病防除効果試験直径12の磁
性ボットに栽培した燕麦(品種:ビクトリア、8葉期)
に冠さび病菌(Pucciniacoronate f
、 sp、 avenae ) 夏胞子をふりかけ接種
し、1日25℃の温室に置いた後、本発明化合物を有効
成分とする薬剤の所定薬量に調製した薬液をターンテー
ブル上でスプレーガンを使用して散布した。散布後25
℃の温室に保管し、接種14日後に葉上に形成された夏
胞子堆数を無処理区と比較してそれぞれの防除効果を試
賎例1と同一の基準で調査した。Table 4 Test Example 4: Oat crown rust control effect test Oat grown in a magnetic bot with a diameter of 12 (variety: Victoria, 8-leaf stage)
Puccinia coronate f.
, sp, avenae) was sprinkled and inoculated and left in a greenhouse at 25°C for one day. Then, a drug solution containing the compound of the present invention as an active ingredient at a predetermined dose was sprayed on a turntable using a spray gun. It was sprayed. 25 days after spraying
The plants were stored in a greenhouse at 14°C, and the number of pediculospores formed on the leaves 14 days after inoculation was compared with that of the untreated plot, and the pesticidal effects of each were investigated using the same criteria as Sample Sample 1.
結果を第5表に示す。The results are shown in Table 5.
第 5 表
試験例5
木材腐朽菌に対する防腐効力試験
1)試験方法
日本木材保存協会(JWPA)の防腐効力試験方法に準
じた。即ち、供試木片(ax2xα5m大の遅相)の木
口面(2X0.5の)を塗料で被覆し、所定a度の薬液
を110±10り/イ塗布し室温で風乾させ、半数の木
片はそのまま供試し、残り半数の木片は耐候操作を行っ
た。Table 5 Test Example 5 Preservative efficacy test against wood-decaying fungi 1) Test method The preservative efficacy test method of the Japan Wood Preservation Association (JWPA) was followed. That is, the end surfaces (2 x 0.5) of test pieces of wood (ax 2 The wood pieces were tested as they were, and the remaining half of the wood pieces were weather-proofed.
しかる後一定の腐朽温度に保たれたナミダタケ等の供試
木材腐朽菌入り腐朽瓶の中に2種の供試木片を2力月保
存した。各区5瓶、−瓶当り木片5個。Thereafter, the two types of test pieces of wood were stored for 2 months in a decaying bottle containing test wood-decaying fungi such as Namida bamboo that was maintained at a constant decay temperature. 5 bottles in each section, - 5 pieces of wood per bottle.
2)試験条件
供試木材腐朽菌 供試木片の樹穐 腐朽温度オオウズラ
タケ スギ 25℃
カワラタケ ブナ 25℃
耐候操作:薬剤処理後約1ケ月経過した試験体の半数に
ついて行う。約26℃
の室内で、室温の静水に30秒浸
漬し、底部に水をはった密閉容器
中に4時間放置し40℃±20時
間乾燥する。この操作を10回反
復する。2) Test conditions Test conditions Wood-decaying fungi Test wood pieces of axe Decaying temperature Versacea japonica Cedar 25°C Kawaratake Beech 25°C Weathering operation: Perform on half of the test specimens about 1 month after chemical treatment. In a room at about 26°C, immerse in still water at room temperature for 30 seconds, leave in a sealed container with water at the bottom for 4 hours, and dry at 40°C ± 20 hours. Repeat this operation 10 times.
3)供試薬剤
本発明化合物を有効成分とし、1%、cL5%、0.2
5%に希釈した白灯油溶液を調整した。3) Test drug The compound of the present invention is used as an active ingredient, 1%, cL5%, 0.2
A white kerosene solution diluted to 5% was prepared.
4)試験結果
腐朽瓶中に保存した供試木片の重量減少率をめ、そして
下記の式により効力値を算出した。4) Test results The weight loss rate of the test pieces stored in the decay bottle was calculated, and the efficacy value was calculated using the following formula.
効力値(%) × 100 結果を下記の第6表に示す。Efficacy value (%) × 100 The results are shown in Table 6 below.
試験例6 防カビ効力試験
2 cm X 2 cm Xα5c!nのブナ片材(木
口面2m×2α)を本発明化合物を有効成分として所定
m1度に希釈した白灯油溶液に′IO秒間浸漬し、風乾
した。半数の木片を試験例5と同様にして耐候操作し、
残り半数はそのまま供試した。かかる操作の後寒天培地
を入れた直径9anのペトリ皿の培地上に5個の木片を
並べ、供試菌の混合胞子懸濁液を噴霧し、ふたをして2
6℃±2℃の悼温室に置き、木片上の供試菌の菌叢の生
育状態を1週毎に4週後1で調査し、下記の基mK従っ
て判定した。Test Example 6 Antifungal Efficacy Test 2 cm X 2 cm Xα5c! A piece of beech wood (end side 2m x 2α) of size n was immersed in a white kerosene solution containing the compound of the present invention as an active ingredient diluted to a predetermined ml degree for 10 seconds and air-dried. Half of the wood pieces were weatherized in the same manner as in Test Example 5,
The remaining half was used as is. After this operation, five pieces of wood were arranged on a Petri dish with a diameter of 9 an inch containing an agar medium, sprayed with a mixed spore suspension of the test bacteria, and covered with a lid.
The wood chips were placed in a greenhouse at 6°C ± 2°C, and the growth status of the bacterial flora of the test bacteria on the wood pieces was examined every week after 4 weeks and judged according to the following mK.
一;菌叢が自限で認められない。1; Bacterial flora is not observed on its own.
士;菌叢の有無不明確。B: The presence or absence of bacterial flora is unclear.
+:菌叢が表面積の10%以下
甘:菌叢が表面積の10〜50%
41 ; 50%以上
供試菌としてはペニシリウム シトリヌム(Penic
illium citrinum )、アスペルギルス
ニガー(Aspergillus niger l 及
びトリコデルマ ビリディ(Trichoderma
viridea )を使用した。+: Bacterial flora is less than 10% of the surface area Sweet: Bacterial flora is 10 to 50% of the surface area 41; More than 50% of the surface area
illium citrinum), Aspergillus niger and Trichoderma viridi.
viridea) was used.
結果を第7表に示す。The results are shown in Table 7.
第 7 表
化合物Bは試験例5と同様、化合物Aはジクロフルアニ
ド(N−ジクロロフルオロメチルチyl−−N’、N’
−’) lチル−N−フェニルスルファミド)を供試
した。Table 7 Compound B is the same as Test Example 5, Compound A is dichlorofluanid (N-dichlorofluoromethylthyl--N', N'
-') l-thyl-N-phenylsulfamide) was tested.
実施例7 抗菌力試験 寒天稀釈法によシ試験を行った。Example 7 Antibacterial activity test The test was conducted using the agar dilution method.
試験方法
PDA培地を使用して、2倍稀釈法で本発明化合物を有
効成分とする薬剤を添加し、25℃又は20℃で5日間
培養し発育阻止最低濃度(MIC>を調査した。Test Method Using a PDA medium, a drug containing the compound of the present invention as an active ingredient was added in a 2-fold dilution method, cultured at 25°C or 20°C for 5 days, and the minimum inhibitory concentration (MIC>) was investigated.
供試菌は下記の通シである。The test bacteria are as follows.
Cv: カワラタケ(Coriolus versic
olor )Tp: オオウズラタケ(Tyromyc
es palustris )Pc: ヒイロタケ(P
ycnoporus coccineus )Sl :
ナミダタケ(5erpula Iacrymans )
Cp : イドタケ(Coniophora pute
ana)Pct : ペニシリウム シトリヌA (P
enicillium citrinumlAn 了ス
ベルギルスニガー(Aspergillus nige
r )Cg : ケトミウム ダミボーサム(Chae
tonium globosum)Tマ ° トリコデ
ルマ ビリディ(T兆boderma viridea
)結果を第8表及び第9表に示す。Cv: Coriolus versic
olor ) Tp: Tyromyc
es palustris) Pc: Hiirotake (P
ycnoporus coccineus ) Sl:
Namidatake (5erpula Iacrymans)
Cp: Coniophora pute
ana) Pct: Penicillium citrine A (P
enicillium citrinumlAn Aspergillus niger
r) Cg: Chaetomium
tonium globosum) Tma ° Trichoderma viridea
) The results are shown in Tables 8 and 9.
第 8 表
化合物Aは試験例6に同じ
第9表
化合物へは試験例6に同じ
処方例1 水和剤
化合物番号1 50s
珪藻土・クレーの混合物 45部
ポリオキシエチレンノニルフェニルエーテル 5部以上
を均一に混合粉砕して水利剤とする。Table 8 Compound A is the same as Test Example 6 Table 9 Compounds are the same as Test Example 6 Prescription Example 1 Wettable powder Compound No. 1 50s Mixture of diatomaceous earth/clay 45 parts Polyoxyethylene nonylphenyl ether 5 parts or more uniformly It is mixed and ground to make an irrigation agent.
処方例2 乳 剤
化合物番号26 20部
テトラヒトOフラン 20部
キシレン 45部
ポリオキシエチレyノニルフェニルエーテルとアルキル
ベンゼンスルホン酸塩の混合物 15部以上を均一に混
合溶解して乳剤とする。Formulation Example 2 Emulsion Compound No. 26 20 parts Tetrahydrofuran 20 parts Xylene 45 parts A mixture of polyoxyethylene ynonyl phenyl ether and alkylbenzene sulfonate 15 parts or more are uniformly mixed and dissolved to prepare an emulsion.
処方例3 粉 剤
化合物番号39 4部
珪藻土・クレー・タルクの混合物 95部ステアリン酸
カルシウム tm
以上を均一に混合粉砕して粉剤とする。Formulation Example 3 Powder Compound No. 39 4 parts Mixture of diatomaceous earth, clay, and talc 95 parts Calcium stearate tm The above are uniformly mixed and pulverized to form a powder.
処方例4 粒 剤
化合物番号8 5部
ベントナイト・クレーの混合物 92部リグニンスルホ
ン酸カルシウム 5部
以上を均一に混合粉砕して適量の水を加えて工く混線し
造粒して粒剤とする。Formulation Example 4 Granules Compound No. 8 5 parts Bentonite-clay mixture 92 parts Calcium ligninsulfonate 5 parts or more are mixed and pulverized uniformly, mixed with an appropriate amount of water, and granulated to obtain granules.
処方例5 油 剤 化合物番号51 1部 ジメチルホルムアミド 5部 白灯油 94部 以上を均一に混合溶解して油剤とする。Prescription example 5 Oil agent Compound number 51 1 part Dimethylformamide 5 parts White kerosene 94 parts The above is uniformly mixed and dissolved to form an oil agent.
特許出願人 日本農薬株式会社
2、 発明(7) 名称 イミダシー−誘導体及び非医
療用殺菌剤3、補正する者
事件との関係 特許出願人
住所 東京都中央区日本橋1丁目2爵5号名称 日本農
薬株式会社
+11 明細書の全文を別紙の通f)浦11゜する。Patent applicant: Nippon Yakuza Co., Ltd. 2, Invention (7) Name: Imidacy-derivatives and non-medical fungicide 3, Relationship with the person making the amendment Patent applicant's address: No. 5, Nihonbashi 1-chome, Chuo-ku, Tokyo Name: Nihon Nohyaku Co., Ltd. +11 Please send the full text of the specification on a separate sheet f) Ura 11゜.
(明1111I誉全文をタイプ#曹したつ内容に変更な
し。)手続補正書
1事件の表示昭和59年 特許願 第109824号2
°発10名称イi p−1−x#4B&ulf:E!<
[711(u13補正する者
事件との関係 特許出願人
4、代 理 人
(をまか 1 名)
5、補IE命令のH付
゛ 「自発」
6、補正の対象
(11明、洲I!Fv発明”) n haな説明の欄−
・4・・−°、:\、
7、補正の内容
(1) 明細4に第12員46行化合物番号40のX4
111のr2−CH20Jを「2− CH30Jに補正
します。(There is no change in the content of Mei 1111I Homare's full text in type #Soshitsu.) Procedural amendment 1 Display of case 1982 Patent application No. 109824 2
°10 name i p-1-x#4B&ulf:E! <
[711 (Relationship with u13 Amendr case Patent applicant 4, agent (1 person) 5. Supplementary IE order with H “Volunteer” 6. Subject of amendment (11 Akira, Shu I! Fv invention”) n ha explanation column-
・4...-°, :\, 7. Contents of amendment (1) X4 of compound number 40 in 12th member line 46 in specification 4
Correct r2-CH20J of 111 to 2-CH30J.
(2) 同第12頁第7行化合物番号41のX欄の[2
−CH,OJをl’−2−CH30J K、かツYn
d )r4− CH2O[4−CH30
5−Cl J 5−CI Jに補正しまを
す。(2) [2] in column X of compound number 41, line 7, page 12
-CH, OJ l'-2-CH30J K, KatsuYn
d) Correct to r4- CH2O[4-CH30 5-Cl J 5-CI J.
、 −′4壜十港潰4±1 4, -'4 bottle 10 ports 4±1 4
Claims (2)
アノアルキル基;アルケニル基;ハロアルケニル基;ア
ルキニル基:アルコキシアルキル基;アルコキシカルボ
ニルアルキル基;了シルオキシアルキル基及びハロゲン
原子で置換されても良いフェノキシアルキル基を示し、
xFi低級ハロアルキル基;低級アルコキシ基;低級ア
ルキルチオ基:低級ハロアルコキシ基;低級ハロアルキ
ルチオ基:アルケニルオキシ基:アルキニルオキシ基;
アルコキシカルボニル基:フェノキシ基及びベンンルオ
キシ基を示しYは同一でも異なっても艮く、水素原子;
〕・aケン原子;低級アルキル基;低級アルコキシ基を
示しnは1又は2の整数を示す。又X及びYFi−緒に
なってアルキレンジオキシ基を表わすこともできる。)
で表わされるイミダゾール誘導体。(1) General formula (11 (wherein R is an alkyl group having 1 to 8 carbon atoms; a cyanoalkyl group; an alkenyl group; a haloalkenyl group; an alkynyl group; an alkoxyalkyl group; an alkoxycarbonylalkyl group; a siloxyalkyl group; represents a phenoxyalkyl group which may be substituted with a group or a halogen atom,
xFi lower haloalkyl group; lower alkoxy group; lower alkylthio group: lower haloalkoxy group; lower haloalkylthio group: alkenyloxy group: alkynyloxy group;
Alkoxycarbonyl group: represents a phenoxy group and a benyloxy group, Y may be the same or different, and a hydrogen atom;
]・a Ken atom; lower alkyl group; lower alkoxy group; n represents an integer of 1 or 2; Also, X and YFi- together can represent an alkylenedioxy group. )
An imidazole derivative represented by
アノアルキル基;アルケニル基]ハaアルケニル基;ア
ルキニル基;アルコキシアルキル基:アルコキシカルボ
ニルアルキル基;アシルオキシアルキル基及ヒハロゲン
原子で置換されても良いフェノキシアルキル基を示し、
Xは低級ノ・ロアルキル基;低級アルコキシ基;低級ア
ルキルチオ基:低級ハロアルコキシ基;低級ハロアルキ
ルチオ基;アルケニルオキシ基;アルキニルオキ−/基
;アルコキシカルボニル基;フェノキシ基及ヒべンジル
オキシ基を示し、Yは同一でも異なっても良く、水素原
子、ノ・ロゲン原子;低級アルキル基;低級アルコキシ
基を示しnは1又Vi2の整数を示す。又X及びYは一
緒になってプルキレンジオキシ基を表わすこともできる
。) で表わされるイミダゾール誘導体を有効成分として含有
することを特徴とする非医療用殺菌剤。(2) General formula (11 (wherein R is an alkyl group having 1 to 8 carbon atoms; a cyanoalkyl group; an alkenyl group) and phenoxyalkyl group which may be substituted with a halogen atom,
X represents a lower alkyl group; a lower alkoxy group; a lower alkylthio group; a lower haloalkoxy group; a lower haloalkylthio group; an alkenyloxy group; an alkynyloxy group; an alkoxycarbonyl group; Y may be the same or different, and represents a hydrogen atom, a hydrogen atom, a lower alkyl group, or a lower alkoxy group, and n represents an integer of 1 or Vi2. Moreover, X and Y together can also represent a purkylenedioxy group. ) A non-medical disinfectant characterized by containing an imidazole derivative represented by the following as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59109824A JPS60255775A (en) | 1984-05-30 | 1984-05-30 | Imidazole derivative and fungicide for non-medical purposes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59109824A JPS60255775A (en) | 1984-05-30 | 1984-05-30 | Imidazole derivative and fungicide for non-medical purposes |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS60255775A true JPS60255775A (en) | 1985-12-17 |
Family
ID=14520137
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP59109824A Pending JPS60255775A (en) | 1984-05-30 | 1984-05-30 | Imidazole derivative and fungicide for non-medical purposes |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS60255775A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2305173A (en) * | 1995-09-16 | 1997-04-02 | Agrevo Uk Ltd | N-(heterocyclylmethylene)-2-(carboxy or heterocyclyl)aniline derivatives as fungicides |
-
1984
- 1984-05-30 JP JP59109824A patent/JPS60255775A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2305173A (en) * | 1995-09-16 | 1997-04-02 | Agrevo Uk Ltd | N-(heterocyclylmethylene)-2-(carboxy or heterocyclyl)aniline derivatives as fungicides |
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