JPS6256873B2 - - Google Patents
Info
- Publication number
- JPS6256873B2 JPS6256873B2 JP53074884A JP7488478A JPS6256873B2 JP S6256873 B2 JPS6256873 B2 JP S6256873B2 JP 53074884 A JP53074884 A JP 53074884A JP 7488478 A JP7488478 A JP 7488478A JP S6256873 B2 JPS6256873 B2 JP S6256873B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- lower alkyl
- weight
- parts
- hydrogen atom
- 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
Links
- 239000000417 fungicide Substances 0.000 claims description 14
- 230000000855 fungicidal effect Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 15
- 241000209094 Oryza Species 0.000 description 13
- 235000007164 Oryza sativa Nutrition 0.000 description 13
- 235000009566 rice Nutrition 0.000 description 13
- 239000003814 drug Substances 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- -1 hydrazone compound Chemical class 0.000 description 9
- 230000003902 lesion Effects 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000011081 inoculation Methods 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 241000221785 Erysiphales Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000207961 Sesamum Species 0.000 description 3
- 235000003434 Sesamum indicum Nutrition 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- BWIHJLOBZMKPKS-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)pyrimidine Chemical class N1C=CC(C=2N=CC=CN=2)=N1 BWIHJLOBZMKPKS-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- XIFVEJXUSTTZKD-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-6-methyl-1h-pyrimidin-4-one Chemical compound N1=C(C)C=C(C)N1C1=NC(=O)C=C(C)N1 XIFVEJXUSTTZKD-UHFFFAOYSA-N 0.000 description 1
- KWSKLMBENWXRSB-UHFFFAOYSA-N 4-chloro-2-(3,5-dimethylpyrazol-1-yl)-6-methylpyrimidine Chemical compound N1=C(C)C=C(C)N1C1=NC(C)=CC(Cl)=N1 KWSKLMBENWXRSB-UHFFFAOYSA-N 0.000 description 1
- XDCIBZVFAIWWIE-UHFFFAOYSA-N 5-butyl-1h-pyrimidin-6-one Chemical compound CCCCC1=CN=CNC1=O XDCIBZVFAIWWIE-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 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
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- XFMJUIKWKVJNDY-UHFFFAOYSA-N diethoxyphosphorylsulfanylmethylbenzene Chemical compound CCOP(=O)(OCC)SCC1=CC=CC=C1 XFMJUIKWKVJNDY-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 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
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
本発明はある種のピラゾリルピリミジン誘導体
およびそれらの農園芸用殺菌剤としての利用に関
する。特に詳しくは本発明は一般式（）
〔ただし、式中R1は水素原子、低級アルキル基ま
たはフエニル基を示し、R2は水素原子または低
級アルキル基を示しR3は
The present invention relates to certain pyrazolylpyrimidine derivatives and their use as agricultural and horticultural fungicides. In particular, the present invention is based on the general formula () [However, in the formula, R 1 represents a hydrogen atom, a lower alkyl group, or a phenyl group, R 2 represents a hydrogen atom or a lower alkyl group, and R 3 represents a hydrogen atom or a lower alkyl group.
【式】基（R4
およびR5は相異なつて水素原子または低級アル
キル置換フエニル基を示すかあるいはまたR4お
よびR5が共同して炭素数６までの飽和の環を形
成してもよい）を示す〕で表わされるピラゾリル
ピリミジン誘導体およびそれを有効成分として含
有する農園芸用殺菌剤に関する。
前記一般式（）で表わされる化合物に類似す
るものとしては２−（３・５−ジメチル−１−ピ
ラゾリル）−４−メチル−６−ヒドロキシピリミ
ジンおよび２−（３・５−ジメチル−１−ピラゾ
リル）−４−フエニル−６−ヒドロキシピリミジ
ンがあり、これら二者については武田研究所年報
第24巻第250〜258頁（1965）において稲のいもち
病に防除活性を有するが同時に稲に対して激しい
薬害を与えるものとして記載されている。
本発明者等は一連のピラゾリルピリミジン系化
合物を合成しかつそれらの農園芸用殺菌剤として
の実用性について鋭意検討した。その結果、前記
一般式（）で表わされる特定の化合物群が稲の
いもち病、稲のごま葉枯病、キユウリのうどんこ
病などに対して極めて顕著な防除活性を有するこ
とを見出した。これら一連の化合物はそれらが有
用植物には全く薬害を与えることなく、また人畜
毒性や魚毒性もなく安全に使用できるので極めて
優れた殺菌剤である。
本発明のこのような特徴は前記文献に記載され
た技術水準からは当業者といえども容易には推考
しがたいものであり、従つて本発明にかかる農園
芸用殺菌剤は実用性が大いに期待される優れた薬
剤である。
前記一般式（）の化合物は次記反応式により
示された方法により製造される。
これらの反応を行う方法を簡単に説明すると次
のとおりである。６−ヒドラジノ体（ａ）は、
特公昭39−4491号公報に記載の方法に従つて対応
する６−クロル体（）をエタノールあるいはイ
ソプロパノールまたはこれらと水との混液中で数
分ないし数時間加熱することにより容易に得られ
る。またR4およびR5が低級アルキルである式
（ｂ）のヒドラゾン体は大過剰の相当するケト
ン類中で酸の存在あるいは不存在下に対応するヒ
ドラジノ体（ａ）を加熱後放冷することにより
結晶として析出する。結晶が析出しない場合は濃
縮することにより結晶として得ることができる。
ヒドラジノ体と反応させるべき反応成分がアルデ
ヒド類または分子量の比較的大きいケトン類であ
る場合には適当な溶媒特によいのはアルコール類
を反応溶媒として30分ないし数時間酸の存在ある
いは不存在下に加熱することにより容易に得られ
る。
次に本発明の化合物についての具体的な製造例
を掲げる。
製造例
２−（３・５−ジメチル−１−ピラゾリル）−４
−メチル−６−ピリミジルクロライド3.3ｇに50
％イソプロパノール100mlと80％ヒドラジンヒド
ラート10mlとを加え、80℃で30分間加熱後放冷す
る。析出した結晶を取すると２−（３・５−ジ
メチル−１−ピラゾリル）−４−メチル−６−ピ
リミジルヒドラジンが淡茶色結晶として2.8ｇ
（収率93％）得られた。エタノール−水の混合溶
媒で再結晶すると白色結晶となり融点184〜186℃
を示した。
かくして得られた２−（３・５−ジメチル−１
−ピラゾリル）−４−メチル−６−ピリミジルヒ
ドラジン4.1ｇ、ｐ−メチルベンズアルデヒド2.4
ｇ、エタノール100mlおよび濃塩酸10滴の混合物
を１時間還流する。冷却後、減圧でエタノールを
留去するとｐ−メチルベンズアルデヒド２−
（３・５−ジメチル−１−ピラゾリル）−４−メチ
ル−６−ピリミジルヒドラゾン（化合物No.１）が
淡黄色結晶として5.9ｇ（収率97％）得られた。
メタノール−水の混合溶媒で再結晶すると白色結
晶となり、融点171〜172℃を示した。
実質上同様な操作により得られる本発明の化合
物およびその物性値を表示すると次のとおりであ
る。[Formula] Group (R 4 and R 5 are different and represent a hydrogen atom or a lower alkyl-substituted phenyl group, or R 4 and R 5 may jointly form a saturated ring having up to 6 carbon atoms) )] and an agricultural and horticultural fungicide containing the same as an active ingredient. Compounds similar to the above general formula () include 2-(3,5-dimethyl-1-pyrazolyl)-4-methyl-6-hydroxypyrimidine and 2-(3,5-dimethyl-1-pyrazolyl). )-4-phenyl-6-hydroxypyrimidine, and these two have been reported in Takeda Research Institute Annual Report, Vol. 24, pp. 250-258 (1965) to have control activity against rice blast, but at the same time, they are aggressive against rice blast. It is described as causing drug damage. The present inventors synthesized a series of pyrazolylpyrimidine compounds and conducted intensive studies on their practicality as agricultural and horticultural fungicides. As a result, it has been found that a specific group of compounds represented by the above general formula () have extremely significant control activity against rice blast, sesame leaf blight of rice, powdery mildew of cucumber, and the like. These series of compounds are extremely excellent fungicides because they do not cause any phytotoxicity to useful plants, nor are they toxic to animals or fish, and can be used safely. Such characteristics of the present invention are difficult to be deduced even by a person skilled in the art from the state of the art described in the above-mentioned documents, and therefore, the agricultural and horticultural fungicide according to the present invention has great practicality. It is a promising and excellent drug. The compound of the general formula () is produced by the method shown by the following reaction formula. A brief explanation of how to perform these reactions is as follows. 6-hydrazino form (a) is
According to the method described in Japanese Patent Publication No. 39-4491, the corresponding 6-chlor compound () can be easily obtained by heating it in ethanol, isopropanol, or a mixture of these and water for several minutes to several hours. In addition, for the hydrazone compound of formula (b) in which R 4 and R 5 are lower alkyl, the corresponding hydrazino compound (a) is heated in the presence or absence of an acid in a large excess of the corresponding ketone, and then allowed to cool. It precipitates as crystals. If crystals do not precipitate, they can be obtained as crystals by concentrating.
When the reaction component to be reacted with the hydrazino compound is an aldehyde or a ketone with a relatively large molecular weight, a suitable solvent is particularly preferable. Easily obtained by heating. Next, specific production examples of the compounds of the present invention are listed. Production example 2-(3,5-dimethyl-1-pyrazolyl)-4
-Methyl-6-pyrimidyl chloride 50 to 3.3g
Add 100 ml of 80% isopropanol and 10 ml of 80% hydrazine hydrate, heat at 80°C for 30 minutes, and then allow to cool. When the precipitated crystals were taken, 2.8g of 2-(3,5-dimethyl-1-pyrazolyl)-4-methyl-6-pyrimidylhydrazine was found as light brown crystals.
(yield 93%). When recrystallized with a mixed solvent of ethanol and water, it becomes white crystals with a melting point of 184-186℃.
showed that. The thus obtained 2-(3,5-dimethyl-1
-pyrazolyl)-4-methyl-6-pyrimidylhydrazine 4.1 g, p-methylbenzaldehyde 2.4
A mixture of g, 100 ml of ethanol and 10 drops of concentrated hydrochloric acid is refluxed for 1 hour. After cooling, ethanol is distilled off under reduced pressure to produce p-methylbenzaldehyde 2-
5.9 g (yield 97%) of (3,5-dimethyl-1-pyrazolyl)-4-methyl-6-pyrimidylhydrazone (Compound No. 1) was obtained as pale yellow crystals.
Recrystallization from a mixed solvent of methanol and water gave white crystals with a melting point of 171-172°C. The compounds of the present invention obtained by substantially similar operations and their physical properties are as follows.
【表】【table】
【表】
本発明の農園芸用殺菌剤を農園芸作物の病害防
除に使用するには、本発明の化合物をそのままか
あるいは水、固体粉末その他の適当な担体を用い
て希釈し、必要に応じて展着剤等の補助剤を加え
て使用するか、または農薬製造に一般的に行われ
ている方法により各種の液体あるいは固体担体と
混合し、必要ならば湿潤剤、展着剤、分散剤、乳
化剤、固着剤等の補助剤を加え水和剤、液剤、乳
剤、粉剤、粒剤、微粒剤等の種々の製剤形態にし
て使用することができる。
これらの製剤を製造するに当つては、液体担体
としては例えば水、芳香族炭化水素類、脂肪族炭
化水素類、アルコール類、エステル類、ケトン
類、極性の大きなジメチルホルムアミド、ジメチ
ルスルホキシド等の溶剤、固体担体としてはクレ
ー、タルク、カオリン、ベントナイト、硅藻土、
炭酸カルシウム、硅酸等の鉱物質粉末類、木粉そ
の他の有機質粉末類を用いることができ、補助剤
としては非イオン、陰イオン、陽イオンおよび両
性の各界面活性剤、リグニンスルホン酸あるいは
その塩、ガム類、脂肪酸塩類、メチルセルロース
等の糊料が挙げられる。
更に必要ならば、他の殺菌剤、殺虫剤、除草
剤、植物生長調節剤、殺線虫剤等の農薬、または
肥料等を混合して用いることもできる。
本発明の農園芸用殺菌剤は病害防除が望まれる
作物に直接散布して用いることができるほか、必
要に応じて水面や土壌表面等の作物の生育環境に
適用することもでき、土壌中に混和して使用する
こともできる。本発明の農園芸用殺菌剤を液剤と
して使用する場合には、通常散布液中に本発明の
化合物が10ないし1000ppmの濃度で含有される
ようにするのが望ましく、濃厚少量散布、航空機
散布等の場合には必要に応じてより濃厚な散布液
として使用することができ、粉剤、粒剤、微粒剤
等として用いる場合には0.3〜30％含まれるよう
にすることが望ましい。
次に本発明の農園芸用殺菌剤の具体例を示す
が、本発明はこれらに限定されるものではない。
例 １
水和剤
化合物No.１の化合物20重量部とポリオキシエチ
レンアルキルアリールエーテル５重量部、リグニ
ンスルホン酸カルシウム３重量部および硅藻土72
重量部とを均一に粉砕混合すれば有効成分20％を
含む水和剤を得る。
例 ２
粒 剤
化合物No.１の化合物５重量部とリグニンスルホ
ン酸カルシウム１重量部、ベントナイト30重量部
およびグレー64重量部とを均一に粉砕混合し、次
に適当量の水を加えて練合した後、造粒して乾燥
すれば、有効成分５％を含む粒剤を得る。
例 ３
粉 剤
化合物No.２の化合物３重量部と無水硅酸微粉末
0.5重量部、ステアリン酸カルシウム0.5重量部、
クレー50重量部およびタルク46重量部とを均一に
粉砕混合すれば有効成分３％を含む粉剤を得る。
例 ４
乳 剤
化合物No.１の化合物20重量部とジメチルホルム
アミド30重量部、キシレン35重量部およびポリオ
キシエチレンアルキルアリールエーテル15重量部
とを均一に溶解混合すれば有効成分20％を含む乳
剤を得る。
次に本発明の化合物の有用性を明確ならしめる
ために試験例を掲げる。
試験例 １
水稲のいもち病防除効果試験（予防）
温室内で直径９cmの素焼鉢で土耕栽培した水稲
（品種 朝日）の第３葉期苗に所定濃度に希釈し
た供試薬液を散布した。散布１日後にいもち病菌
の胞子懸濁液を噴霧接種した。接種後一夜湿温条
件下（湿度95〜100％、温度24〜25℃）に保つ
た。接種５日後に第３葉の１葉あたりの病斑数を
調査し、次式により防除価を算出した。また稲に
対する薬害を次記の指標により調査した。その結
果は第２表のとおりである。
防除価（％）＝（１−散布区の病斑数／無散布区の病斑
数）×100
薬害の調査指標
５：激甚
４：甚
３：多
２：若干
１：わずか
０：なし[Table] In order to use the agricultural and horticultural fungicide of the present invention for disease control of agricultural and horticultural crops, the compound of the present invention may be used as it is or diluted with water, solid powder or other suitable carrier, as required. It can be used by adding adjuvants such as spreading agents, or mixed with various liquid or solid carriers by methods commonly used in agricultural chemical manufacturing, and if necessary, wetting agents, spreading agents, and dispersing agents. By adding auxiliary agents such as emulsifiers and fixing agents, it can be used in various formulations such as wettable powders, solutions, emulsions, powders, granules, and fine granules. In producing these preparations, liquid carriers such as water, aromatic hydrocarbons, aliphatic hydrocarbons, alcohols, esters, ketones, and highly polar solvents such as dimethylformamide and dimethyl sulfoxide are used. , solid carriers include clay, talc, kaolin, bentonite, diatomaceous earth,
Mineral powders such as calcium carbonate and silicic acid, wood flour and other organic powders can be used.As adjuvants, nonionic, anionic, cationic and amphoteric surfactants, ligninsulfonic acid or its Thickening agents such as salts, gums, fatty acid salts, and methyl cellulose can be mentioned. Furthermore, if necessary, other fungicides, insecticides, herbicides, plant growth regulators, agricultural chemicals such as nematicides, or fertilizers may be used in combination. The agricultural and horticultural fungicide of the present invention can be used by directly spraying on crops for which disease control is desired, and if necessary, it can also be applied to crop growing environments such as water surfaces and soil surfaces. They can also be used in combination. When the agricultural and horticultural fungicide of the present invention is used as a liquid agent, it is desirable that the compound of the present invention be contained in the spray solution at a concentration of 10 to 1000 ppm. In this case, it can be used as a more concentrated spray solution if necessary, and when used as a powder, granules, fine granules, etc., it is desirable to have a content of 0.3 to 30%. Next, specific examples of the agricultural and horticultural fungicide of the present invention will be shown, but the present invention is not limited thereto. Example 1 Wettable powder: 20 parts by weight of Compound No. 1, 5 parts by weight of polyoxyethylene alkylaryl ether, 3 parts by weight of calcium lignin sulfonate, and 72 parts by weight of diatomaceous earth.
By uniformly pulverizing and mixing parts by weight, a wettable powder containing 20% of the active ingredient can be obtained. Example 2 Granules 5 parts by weight of Compound No. 1, 1 part by weight of calcium lignosulfonate, 30 parts by weight of bentonite and 64 parts by weight of gray were uniformly ground and mixed, then an appropriate amount of water was added and kneaded. After that, it is granulated and dried to obtain granules containing 5% of the active ingredient. Example 3 Powder 3 parts by weight of compound No. 2 and silicic anhydride fine powder
0.5 parts by weight, 0.5 parts by weight of calcium stearate,
By uniformly grinding and mixing 50 parts by weight of clay and 46 parts by weight of talc, a powder containing 3% of the active ingredient is obtained. Example 4 Emulsion If 20 parts by weight of Compound No. 1, 30 parts by weight of dimethylformamide, 35 parts by weight of xylene and 15 parts by weight of polyoxyethylene alkylaryl ether are uniformly dissolved and mixed, an emulsion containing 20% of the active ingredient can be obtained. obtain. Next, test examples are listed in order to clarify the usefulness of the compounds of the present invention. Test Example 1 Rice blast control effect test (prevention) A test chemical solution diluted to a predetermined concentration was sprayed on third leaf stage seedlings of paddy rice (variety Asahi) grown in clay pots with a diameter of 9 cm in a greenhouse. One day after the spraying, a spore suspension of the blast fungus was inoculated by spraying. After inoculation, the cells were kept under humid temperature conditions (humidity 95-100%, temperature 24-25°C) overnight. Five days after inoculation, the number of lesions per leaf on the third leaf was investigated, and the control value was calculated using the following formula. In addition, chemical damage to rice was investigated using the following indicators. The results are shown in Table 2. Control value (%) = (1 - number of lesions in the sprayed area / number of lesions in the non-sprayed area) x 100 Investigation index 5 for drug damage: Severe 4: Severe 3: Many 2: Slightly 1: Slightly 0: None
【表】
表中比較薬剤１、２および３はそれぞれ後記式
の化合物を示し、また比較薬剤４はＯ・Ｏ−ジイ
ソプロピルＳ−ベンジルホスホロチオレートを含
有する市販の殺菌剤（商品名キタジンＰ乳剤）で
ある。[Table] Comparative drugs 1, 2, and 3 in the table are compounds of the following formulas, and comparative drug 4 is a commercially available fungicide containing O.O-diisopropyl S-benzyl phosphorothiolate (trade name Kitazine P). emulsion).
【式】【formula】
【式】【formula】
【式】
試験例 ２
水稲のいもち病防除効果試験（治療効果）
温室内で直径９cmの素焼鉢で土耕栽培した水稲
（品種 朝日）の第３葉期苗にいもち病菌の胞子
懸濁液を噴霧接種した。接種後一夜湿室条件下
（湿度95〜100％、温度24〜25℃）に保つた。接種
１日後に所定濃度に希釈した供試薬液を散布し
た。散布５日後に試験例１と同様に防除価および
薬害程度を調査した。
なお比較薬剤は試験例１と同じものを使用し
た。その結果は次表のとおりである。[Formula] Test Example 2 Rice blast control effect test (therapeutic effect) A spore suspension of blast fungus was applied to the third leaf stage seedlings of paddy rice (variety Asahi) grown in clay pots with a diameter of 9 cm in a greenhouse. Spray inoculated. After inoculation, the cells were kept under moist room conditions (humidity 95-100%, temperature 24-25°C) overnight. One day after inoculation, a test chemical solution diluted to a predetermined concentration was sprayed. Five days after spraying, the control value and degree of chemical damage were investigated in the same manner as in Test Example 1. Note that the same comparative drug as in Test Example 1 was used. The results are shown in the table below.
【表】
試験例 ３
水稲ごま葉枯病防除効果試験
温室内で直径９cmの素焼鉢で土耕栽培した水稲
（品種 朝日）の第４本葉期苗に所定濃度に希釈
した薬液を散布し、散布１日後に稲ごま葉枯病苗
の分生胞子懸濁液を噴霧接種した。接種５日後に
第４葉の１葉あたりの病斑数を調査し、次式によ
り防除価を算出した。また試験例１と同様な方法
により稲に対する薬害を調査した。
防除価（％）＝（１−散布区の病斑数／無散布区の病斑
数）×100
その結果は第４表のとおりである。[Table] Test Example 3 Paddy rice sesame leaf blight control effect test A chemical solution diluted to a predetermined concentration was sprayed on the fourth true leaf stage seedlings of paddy rice (variety Asahi) grown in clay pots with a diameter of 9 cm in a greenhouse. One day after the spraying, a conidial suspension of rice and sesame leaf blight diseased seedlings was spray inoculated. Five days after inoculation, the number of lesions per leaf on the fourth leaf was investigated, and the control value was calculated using the following formula. In addition, chemical damage to rice was investigated using the same method as in Test Example 1. Control value (%) = (1 - number of lesions in sprayed area/number of lesions in non-sprayed area) x 100 The results are shown in Table 4.
【表】
表中比較薬剤１、２および３は試験例１と同じ
であり、そして比較薬剤４は２・４−ジクロロ−
６−（Ｏ−クロロアニリノ）−１・３・５−トリア
ジン（一般名トリアジン）を含有する市販の殺菌
剤である。
試験例 ４
キユウリうどんこ病防除効果試験
温室内で直径９cmの素焼鉢で土耕栽培したキユ
ウリ（品種 相模半白）の第１葉期苗に所定濃度
に希釈した薬液各10mlを散布し、一夜放置後にう
どんこ病菌胞子懸濁液を噴霧接種した。接種10日
後に病斑面積歩合（％）を調査して下記式により
防除価を算出した。
防除価（％）＝（１−散布区の病斑面積歩合／無散布区
の病斑面積歩合）
×100
その結果は第５表のとおりである。[Table] Comparative drugs 1, 2 and 3 in the table are the same as Test Example 1, and comparative drug 4 is 2,4-dichloro-
It is a commercially available fungicide containing 6-(O-chloroanilino)-1,3,5-triazine (common name: triazine). Test example 4 Powdery mildew control effect test on cucumber Powdery mildew control effect 10 ml of each chemical solution diluted to a specified concentration was sprayed on the first leaf stage seedlings of cucumber (variety: Sagami Hanshiro) cultivated in clay pots with a diameter of 9 cm in a greenhouse, and left overnight. After standing, a powdery mildew spore suspension was spray inoculated. Ten days after inoculation, the lesion area ratio (%) was investigated and the control value was calculated using the following formula. Control value (%) = (1 - percentage of lesion area in sprayed area/percentage of lesion area in non-sprayed area) x 100 The results are shown in Table 5.
【表】
表中比較薬剤１および２は試験例１のそれぞれ
比較薬剤１および３に同じであり、そして比較薬
剤３は市販の２−ジメチルアミノ−４−メチル−
５−ブチル−６−ヒドロキシピリミジンを含有す
る殺菌剤（商品名ミルカーブ液剤）である。[Table] Comparative drugs 1 and 2 in the table are the same as comparative drugs 1 and 3 of Test Example 1, respectively, and comparative drug 3 is a commercially available 2-dimethylamino-4-methyl-
This is a fungicide (trade name: Milcarb liquid) containing 5-butyl-6-hydroxypyrimidine.
Claims (1)
たはフエニル基を示し、R2は水素原子または低
級アルキル基を示し、R3は【式】基 （R4およびR5は相異なつて水素原子または低級ア
ルキル置換フエニル基を示すかあるいはまたR4
およびR5が共同して炭素数６までの飽和の環を
形成してもよい）を示す〕で表わされるピラゾリ
ルピリミジン誘導体。 ２ 一般式 〔ただし、式中R1は水素原子、低級アルキル基ま
たはフエニル基を示し、R2は水素原子または低
級アルキル基を示し、R3は【式】基 （R4およびR5は同一または相異なつて水素原子ま
たは低級アルキル置換フエニル基を示すかあるい
はまたR4およびR5が共同して炭素数６までの飽
和の環を形成してもよい）を示す〕で表わされる
ピラゾリルピリミジン誘導体を有効成分として含
有する農園芸用殺菌剤。[Claims] 1. General formula [However, in the formula, R 1 represents a hydrogen atom, a lower alkyl group, or a phenyl group, R 2 represents a hydrogen atom or a lower alkyl group, and R 3 represents a [formula] group (R 4 and R 5 are hydrogen represents an atom or lower alkyl substituted phenyl group or also R 4
and R 5 may jointly form a saturated ring having up to 6 carbon atoms. 2 General formula [However, in the formula, R 1 represents a hydrogen atom, a lower alkyl group, or a phenyl group, R 2 represents a hydrogen atom or a lower alkyl group, and R 3 represents a [formula] group (R 4 and R 5 are the same or different represents a hydrogen atom or a lower alkyl-substituted phenyl group, or R 4 and R 5 may jointly form a saturated ring having up to 6 carbon atoms. An agricultural and horticultural fungicide containing as
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7488478A JPS5536402A (en) | 1978-06-22 | 1978-06-22 | Derivative of pyrazolylpyrimidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7488478A JPS5536402A (en) | 1978-06-22 | 1978-06-22 | Derivative of pyrazolylpyrimidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5536402A JPS5536402A (en) | 1980-03-14 |
| JPS6256873B2 true JPS6256873B2 (en) | 1987-11-27 |
Family
ID=13560227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7488478A Granted JPS5536402A (en) | 1978-06-22 | 1978-06-22 | Derivative of pyrazolylpyrimidine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5536402A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000186089A (en) * | 1998-12-22 | 2000-07-04 | Ube Ind Ltd | 5-azolylpyrimidine derivative, its production and microbicide for agriculture and horticulture |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5618564A (en) * | 1979-07-20 | 1981-02-21 | Tsuji Seiyu Kk | Preparation of mustard |
| JPS5751835A (en) * | 1980-08-18 | 1982-03-26 | Staeubli Ag | Method and dobby machine for aligning all helds of loom |
-
1978
- 1978-06-22 JP JP7488478A patent/JPS5536402A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5618564A (en) * | 1979-07-20 | 1981-02-21 | Tsuji Seiyu Kk | Preparation of mustard |
| JPS5751835A (en) * | 1980-08-18 | 1982-03-26 | Staeubli Ag | Method and dobby machine for aligning all helds of loom |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5536402A (en) | 1980-03-14 |
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