JPH0362708B2 - - Google Patents
Info
- Publication number
- JPH0362708B2 JPH0362708B2 JP19609487A JP19609487A JPH0362708B2 JP H0362708 B2 JPH0362708 B2 JP H0362708B2 JP 19609487 A JP19609487 A JP 19609487A JP 19609487 A JP19609487 A JP 19609487A JP H0362708 B2 JPH0362708 B2 JP H0362708B2
- Authority
- JP
- Japan
- Prior art keywords
- integer
- halogen atom
- parts
- compound
- group
- 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
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 230000003902 lesion Effects 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- 240000008067 Cucumis sativus Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 3
- KYWYAWFSWFSPAY-UHFFFAOYSA-N 1,1,3-trimethyl-2,3-dihydroinden-4-amine Chemical compound C1=CC(N)=C2C(C)CC(C)(C)C2=C1 KYWYAWFSWFSPAY-UHFFFAOYSA-N 0.000 description 2
- -1 2-chloro-N-(1-chloro-3-methylindan-4-yl)pyridine-3-carboxamide 4-amino-1-chloro-3-methylindan Chemical compound 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241001465180 Botrytis Species 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical class NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DZSJGYKKLRZRMS-UHFFFAOYSA-N 1,1-dimethyl-2,3-dihydroinden-4-amine Chemical compound C1=CC=C(N)C2=C1C(C)(C)CC2 DZSJGYKKLRZRMS-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QWIIJVGEBIQHSW-UHFFFAOYSA-N 2-chloro-3-(chloromethyl)pyridine Chemical compound ClCC1=CC=CN=C1Cl QWIIJVGEBIQHSW-UHFFFAOYSA-N 0.000 description 1
- JWAMPRHAFCNLIK-UHFFFAOYSA-N 2-chloro-n-(1,1-dimethyl-2,3-dihydroinden-4-yl)pyridine-3-carboxamide Chemical compound CC1(C)CCC2=C1C=CC=C2NC(=O)C1=CC=CN=C1Cl JWAMPRHAFCNLIK-UHFFFAOYSA-N 0.000 description 1
- RXTRRIFWCJEMEL-UHFFFAOYSA-N 2-chloropyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1Cl RXTRRIFWCJEMEL-UHFFFAOYSA-N 0.000 description 1
- QBQKKBSREGCHPO-UHFFFAOYSA-N 2-fluoro-n-(1,1,3-trimethyl-2,3-dihydroinden-4-yl)pyridine-3-carboxamide Chemical compound C=12C(C)CC(C)(C)C2=CC=CC=1NC(=O)C1=CC=CN=C1F QBQKKBSREGCHPO-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
〔産業上の利用分野〕
本発明はピリジン−３−カルボン酸アミド誘導
体およびこれを有効成分とする農園芸用殺菌剤に
関する。
〔従来の技術及び発明が解決しようとする問題
点〕
従来ある種のピリジンカルボン酸アミド誘導体
には殺菌効果等の生物活性を有するものがあるこ
とは知られている。例えば、ドイツ公開特許第
2417216号明細書には
[Industrial Application Field] The present invention relates to a pyridine-3-carboxylic acid amide derivative and an agricultural and horticultural fungicide containing the same as an active ingredient. [Prior Art and Problems to be Solved by the Invention] It has been known that some pyridinecarboxylic acid amide derivatives have biological activities such as bactericidal effects. For example, German published patent no.
In the specification of No. 2417216
【式】で表わされ
る化合物が、又ドイツ公開特許第2611601号明細
書にはThe compound represented by [Formula] is also described in German Published Patent Application No. 2611601
【式】で表わされ
る化合物が、特開昭58−140054号明細書には
The compound represented by the formula is described in JP-A No. 58-140054.
【式】で表わされる化合物
が、又、WO86／02641号明細書には、
The compound represented by [Formula] is also described in WO86/02641 as follows:
すなわち、本発明の要旨は下記一般式（）
（上記式中、Ｘはハロゲン原子、メチル基または
トリフルオロメチル基を表わし、Ｒは低級アルキ
ル基またはハロゲン原子を表わし、ｎは１〜６の
整数を表わし、ｍは０または１の整数を表わす）
で示されるピリジン−３−カルボン酸アミド誘導
体、およびこれを有効成分とする農園芸用殺菌剤
に存する。
以下に本発明を詳細に説明する。
前記式（）に於いて、Ｘはフツ素原子、塩素
原子、臭素原子若しくはヨウ素原子等のハロゲン
原子またはメチル基、トリフルオロメチル基を表
わす。Ｒはメチル基、エチル基、ｎ−プロピル
基、iso−プロピル基等の炭素数１〜５の直鎖ま
たは分岐していても良い低級アルキル基、好まし
くは炭素数１〜３の低級アルキル基；またはフツ
素原子、塩素原子、臭素原子若しくはヨウ素原子
等のハロゲン原子を表わす。ｎは１〜６の整数で
あり、ｎが２〜６の整数の場合、置換基Ｒは互い
に等しくても、または異なつていてもよい。ｎは
好ましくは１〜５の整数である。
一般式（）で示される本発明化合物を具体的
に例示すると表−１の通りであるが、本発明化合
物は、これらのみに限定されるものではない。
That is, the gist of the present invention is the following general formula () (In the above formula, X represents a halogen atom, a methyl group or a trifluoromethyl group, R represents a lower alkyl group or a halogen atom, n represents an integer of 1 to 6, and m represents an integer of 0 or 1. ) A pyridine-3-carboxylic acid amide derivative represented by the following formula, and an agricultural and horticultural fungicide containing the same as an active ingredient. The present invention will be explained in detail below. In the above formula (), X represents a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, or a methyl group or a trifluoromethyl group. R is a lower alkyl group having 1 to 5 carbon atoms which may be linear or branched, such as a methyl group, ethyl group, n-propyl group, iso-propyl group, preferably a lower alkyl group having 1 to 3 carbon atoms; Alternatively, it represents a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. n is an integer of 1 to 6, and when n is an integer of 2 to 6, the substituents R may be equal to or different from each other. n is preferably an integer of 1-5. Specific examples of the compounds of the present invention represented by the general formula () are shown in Table 1, but the compounds of the present invention are not limited to these.
【表】【table】
次に本発明を実施例をあげて更に具体的に説明
するが、本発明はその要旨を超えない限り、以下
の実施例に限定されるものではない。
なお以下、「部」は「重量部」を示す。また、
製造例で合成した本発明化合物はいずれも元素分
析、IRスペクトル、NMRスペクトル等によりそ
の構造を確認した。
製造例 １
２−クロル−Ｎ−（１，１−ジメチルインダン
−４−イル）ピリジン−３−カルボキサミドの
合成
４−アミノ−１，１−ジメチルインダン200mg
（1.2ｍmol）、ピリジン0.15ｇ（1.9ｍmol）の酢酸
エチル15ml溶液に、氷冷下２−クロルニコチン酸
クロリド0.24ｇ（1.4ｍmol）を加え、１時間室温
にて撹拌した。反応溶液は氷水中に注加し、酢酸
エチルにて抽出した。抽出液は水洗し、芒硝乾燥
した後、減圧濃縮した。得られた白色残渣をヘキ
サンにて再結晶化を行ない、白色結晶300mg（表
−２に記載の化合物No.１）を得た。収率は80.4％
であつた。
製造例 ２
２−クロル−Ｎ−（１−クロル−３−メチルイ
ンダン−４−イル）ピリジン−３−カルボキサ
ミドの合成
４−アミノ−１−クロル−３−メチルインダン
１ｇ（5.5ｍmol）、トリエチルアミン0.7ｇ（6.9
ｍmol）のテトラヒドロフラン15ml溶液に氷冷下
２−クロルニコチン酸クロリド1.1ｇ（6.2ｍmol）
を加えた。次いで室温にて１時間撹拌した。反応
溶液は氷水中に注加し、酢酸エチルにて抽出し
た。抽出液は水洗し、芒硝乾燥した後、減圧濃縮
した。得られた残渣をシリカゲルクロマトグラフ
イーにて分離精製し、（展開溶媒ｎ−ヘキサン：
酢酸エチル＝２：１）白色結晶1.3ｇ（表−２に
記載の化合物No.−６）を得た。収率は75％であつ
た。
製造例 ３
２−フルオロ−Ｎ−（１，１，３−トリメチル
インダン−４−イル）ピリジン−３−カルボキ
サミドの合成
２−クロルニコチン酸クロリド2.6ｇ（14.8ｍ
mol）のスルホラン溶液15mlにフツ化カリウム
2.6ｇ（46.4ｍmol）を加え155℃にて６時間加熱
撹拌した。冷却後析出した結晶を別した。液
を、４−アミノ−１，１，３−トリメチルインダ
ン２ｇ（11.4ｍmol）、トリエチルアミン1.6ｇ
（15.8ｍmol）のトルエン10ml溶液に氷冷下滴下
した。次いで室温にて２時間撹拌した。反応溶液
にトルエン30mlを加え、水洗し、芒硝乾燥した
後、減圧濃縮した。得られた残渣をシリカゲルク
ロマトグラフイーにて分離精製し、（展開溶媒ｎ
−ヘキサン：酢酸エチル＝４：１）油状物質1.6
ｇ（表−２に記載の化合物No.−９）を得た。収率
は47％であつた。
製造例 ４
製造例１及び２の方法に準じて、表−２記載の
本発明化合物を製造した。
EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. Note that hereinafter, "parts" indicate "parts by weight." Also,
The structures of the compounds of the present invention synthesized in the production examples were confirmed by elemental analysis, IR spectra, NMR spectra, etc. Production example 1 Synthesis of 2-chloro-N-(1,1-dimethylindan-4-yl)pyridine-3-carboxamide 200 mg of 4-amino-1,1-dimethylindan
To a solution of 0.15 g (1.9 mmol) of pyridine in 15 ml of ethyl acetate was added 0.24 g (1.4 mmol) of 2-chlornicotinic acid chloride under ice cooling, and the mixture was stirred at room temperature for 1 hour. The reaction solution was poured into ice water and extracted with ethyl acetate. The extract was washed with water, dried over Glauber's salt, and then concentrated under reduced pressure. The obtained white residue was recrystallized from hexane to obtain 300 mg of white crystals (Compound No. 1 listed in Table 2). Yield is 80.4%
It was hot. Production Example 2 Synthesis of 2-chloro-N-(1-chloro-3-methylindan-4-yl)pyridine-3-carboxamide 4-amino-1-chloro-3-methylindan 1 g (5.5 mmol), triethylamine 0.7 g (6.9
1.1 g (6.2 mmol) of 2-chlornicotinyl chloride in 15 ml of tetrahydrofuran solution under ice cooling.
added. The mixture was then stirred at room temperature for 1 hour. The reaction solution was poured into ice water and extracted with ethyl acetate. The extract was washed with water, dried over Glauber's salt, and then concentrated under reduced pressure. The obtained residue was separated and purified by silica gel chromatography (developing solvent n-hexane:
1.3 g of white crystals (ethyl acetate = 2:1) (compound No.-6 listed in Table-2) were obtained. The yield was 75%. Production Example 3 Synthesis of 2-fluoro-N-(1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide 2.6 g (14.8 m
Potassium fluoride in 15 ml of sulfolane solution (mol)
2.6 g (46.4 mmol) was added, and the mixture was heated and stirred at 155°C for 6 hours. After cooling, the precipitated crystals were separated. The liquid was mixed with 2 g (11.4 mmol) of 4-amino-1,1,3-trimethylindan and 1.6 g of triethylamine.
(15.8 mmol) was added dropwise to a 10 ml solution of toluene under ice cooling. The mixture was then stirred at room temperature for 2 hours. 30 ml of toluene was added to the reaction solution, washed with water, dried over Glauber's salt, and then concentrated under reduced pressure. The obtained residue was separated and purified by silica gel chromatography (developing solvent n
-Hexane:ethyl acetate = 4:1) oily substance 1.6
g (Compound No.-9 listed in Table-2) was obtained. The yield was 47%. Production Example 4 According to the method of Production Examples 1 and 2, the compounds of the present invention shown in Table 2 were produced.
【表】
製造例 ５
２−トリフルオロメチル−Ｎ−（１，１，３−
トリメチルインダン−４−イル）ピリジン−３
−カルボキサミドの合成
４−アミノ−１，１，３−トリメチルインダン
0.73ｇ（4.2ｍmol）、トリエチルアミン1.5ｇ
（14.9ｍmol）の酢酸エチル60ml溶液に、氷冷下
２−トリフルオロニコチン酸クロリド1.10ｇ
（5.2ｍmol）を加え、３時間室温にて撹拌した。
反応溶液を水洗し芒硝乾燥した後、減圧濃縮し
た。得られた残渣をヘキサン−酢酸エチルにて再
結晶化を行ない、白色結晶1.12ｇ（表−３に記載
の化合物No.10）を得た。収率は80.6％であつた。
製造例 ６
製造例５の方法に準じて表−３の本発明化合物
を製造した。[Table] Production example 5 2-trifluoromethyl-N-(1,1,3-
trimethylindan-4-yl)pyridine-3
-Synthesis of carboxamide 4-amino-1,1,3-trimethylindan
0.73g (4.2mmol), triethylamine 1.5g
(14.9 mmol) in 60 ml of ethyl acetate solution under ice-cooling, 1.10 g of 2-trifluoronicotinic acid chloride.
(5.2 mmol) was added and stirred at room temperature for 3 hours.
The reaction solution was washed with water, dried with sodium sulfate, and then concentrated under reduced pressure. The obtained residue was recrystallized from hexane-ethyl acetate to obtain 1.12 g of white crystals (Compound No. 10 listed in Table 3). The yield was 80.6%. Production Example 6 The compounds of the present invention shown in Table 3 were produced according to the method of Production Example 5.
【表】
製剤例 １
化合物No.１を20部、珪藻土75部、アルキルベン
ゼンスルホン酸を主成分とする界面活性剤５部を
均一に粉砕混合して水和剤を得た。
製剤例 ２
化合物No.10を40部、ホワイトカーボン10部、珪
藻土47部、“ソルポール”5039（東邦化学工業(株)社
商標、ポリオキシエチレンアルキルアリールエー
テルスルホネートを主成分とする界面活性剤）３
部を均一に粉砕混合して水和剤を得た。
製剤例 ３
化合物No.２を30部、“ソルポール”3005X（東邦
化学工業(株)社商標、非イオン系界面活性剤と陰イ
オン系界面活性剤との混合物）15部、キシレン25
部、ジメチルホルムアミド30部を混合溶解して乳
剤を得た。
製剤例 ４
化合物No.１を２部とＮ，Ｎ−カオリンクレー
（土屋カオリン社製）98部とを混合粉砕して粉剤
を得た。
次に、試験例をあげることにより、本発明の化
合物の農園芸用殺菌剤としての有用性を明らかに
する。
なお、本発明の化合物は表−２〜３の化合物番
号で示し、比較対照に用いた化合物は下記表−４
の化合物記号で示す。[Table] Formulation Example 1 A wettable powder was obtained by uniformly grinding and mixing 20 parts of Compound No. 1, 75 parts of diatomaceous earth, and 5 parts of a surfactant whose main component is alkylbenzenesulfonic acid. Formulation example 2 40 parts of compound No. 10, 10 parts of white carbon, 47 parts of diatomaceous earth, "Solpol" 5039 (trademark of Toho Chemical Co., Ltd., surfactant whose main component is polyoxyethylene alkylaryl ether sulfonate) 3
A wettable powder was obtained by uniformly pulverizing and mixing the two parts. Formulation example 3 30 parts of compound No. 2, 15 parts of "Solpol" 3005X (trademark of Toho Chemical Industry Co., Ltd., a mixture of nonionic surfactant and anionic surfactant), 25 parts of xylene
1 part and 30 parts of dimethylformamide were mixed and dissolved to obtain an emulsion. Formulation Example 4 Two parts of Compound No. 1 and 98 parts of N,N-kaolin clay (manufactured by Tsuchiya Kaolin Co., Ltd.) were mixed and ground to obtain a powder. Next, by giving test examples, the usefulness of the compound of the present invention as an agricultural and horticultural fungicide will be clarified. The compounds of the present invention are shown by compound numbers in Tables 2 and 3, and the compounds used for comparison are shown in Table 4 below.
It is shown by the compound symbol.
【表】【table】
【表】
試験例 １
薬剤感受性のキユウリ灰色かび病防除効果試験
径６cmのポツトに育苗した子葉期のキユウリ
（品種：四葉）に製剤例１と同様にして調製した
水和剤を水で所定濃度に希釈して１ポツト当り10
mlの割合で茎葉散布した。薬液風乾後薬剤感受性
の灰色かび病菌ポトリテイス シネリア
（Botrytis cinerea）を噴霧接種し、接種後４日
間、23℃の湿室に保つた後発病状態を調査した。
調査方法は下記の方法によつた。すなわち発病度
は調査葉の発病面積歩合を求めて、その程度に応
じて０、１、３、５の指数に分類し各発病指数に
対応する葉数n0、n1、n3、n5を調査し、次式より
算出した（ｎは調査全葉数）。[Table] Test Example 1 Effect test on control of gray mold disease on drug-sensitive cucumbers A wettable powder prepared in the same manner as Formulation Example 1 was added to cucumbers (variety: four-leaf) in the cotyledon stage grown in pots with a diameter of 6 cm at a predetermined concentration with water. diluted to 10 per pot
Sprayed on foliage at a rate of ml. After the chemical solution was air-dried, the drug-susceptible gray mold fungus Botrytis cinerea was spray inoculated and kept in a humid room at 23°C for 4 days after inoculation to investigate the late onset of the disease.
The investigation method was as follows. In other words, the disease severity is calculated by calculating the percentage of diseased area of the investigated leaves, classifying them into indexes of 0, 1, 3, and 5 according to the severity, and calculating the number of leaves corresponding to each disease index, n 0 , n 1 , n 3 , n 5 was investigated and calculated using the following formula (n is the total number of leaves investigated).
【表】
発病度＝０×n0＋１×n1＋３×n3＋５×n5／ｎ
防除価は次の式より算出した。
防除価（％）＝（無処理区の発病度
）−（処理区の発病度）／（無処理区の発病度）×100
結果を表−５に示す。[Table] Disease severity = 0×n 0 +1×n 1 +3×n 3 +5×n 5 /n The control value was calculated using the following formula. Control value (%) = (Incidence in untreated area) - (Incidence in treated area) / (Incidence in untreated area) x 100 The results are shown in Table 5.
【表】
試験例 ２
薬剤耐性のキユウリ灰色かび病防除効果試験
径６cmのポツトに育苗した子葉期のキユウリ
（品種：四葉）に製剤例１と同様にして調製した
水和剤を水で所定濃度に希釈して１ポツト当り10
mlの割合で茎葉散布した。薬液風乾後薬剤耐性の
灰色かび病菌ボトリテイス シネリア（Botrytis
cinerea）を噴霧接種し、接種後４日間、23℃の
湿室に保つた後発病状態を調査し、試験例１と同
様にして防除価を算出した。結果を表−６に示
す。[Table] Test Example 2 Drug-resistant cucumber Botrytis gray mold control efficacy test A wettable powder prepared in the same manner as Formulation Example 1 was added to a cotyledon stage cucumber (variety: four-leaf) seedlings grown in pots with a diameter of 6 cm at a predetermined concentration with water. diluted to 10 per pot
Sprayed on foliage at a rate of ml. After air-drying the chemical solution, the chemical-resistant botrytis fungus Botrytis cinerea
cinerea) was spray-inoculated and kept in a humid room at 23°C for 4 days after inoculation, and the subsequent disease state was investigated, and the control value was calculated in the same manner as in Test Example 1. The results are shown in Table-6.
【表】
試験例 ３
稲紋枯病防除効果試験
径６cmのポツトに育苗した３〜４葉期の稲（品
種：日本晴）に製剤例１と同様にして調製した水
和剤を水で所定濃度に希釈して１ポツト当り10ml
の割合で茎葉散布した。薬液風乾後、YG培地で
培養した紋枯病菌リゾクトニア ソラニ
（Ryizoctonia solani）の菌系懸濁液を噴霧接種
し、29℃の湿室に40時間保つた後、温室内水槽中
に３日間放置し、現われてくる病斑の発病度合を
測定して下記の式により防除価を算出した。結果
は表−７に示す。
防除価（％）＝（無処理区１葉当りの発病指数
）−（処理区１葉当りの発病指数）／（無処理区１葉当
りの発病指数）×100[Table] Test Example 3 Rice sheath blight control efficacy test A wettable powder prepared in the same manner as Formulation Example 1 was added to rice seedlings (variety: Nipponbare) at the 3rd to 4th leaf stage grown in pots with a diameter of 6cm at a predetermined concentration with water. Dilute to 10ml per pot
Sprayed on foliage at a rate of After the chemical solution was air-dried, it was spray inoculated with a fungal suspension of the sheath blight fungus Ryizoctonia solani cultured in YG medium, kept in a humid room at 29℃ for 40 hours, and then left in an aquarium in a greenhouse for 3 days. Then, the severity of the lesions that appeared was measured and the control value was calculated using the following formula. The results are shown in Table-7. Control value (%) = (Incidence index per leaf in untreated area) - (Incidence index per leaf in treated area) / (Incidence index per leaf in untreated area) x 100
【表】
試験例 ４
コムギ赤さび病防除効果試験
径６cmのポツトに育苗した１−２葉期のコムギ
（品種：農林61号）に、試験例１と同様にして調
製した水和剤を水で所定濃度に希釈して、１ポツ
ト当り10mlの割合で茎葉散布した。薬液風乾後、
コムギ赤さび病菌プシニア レコンデイタ
（Puccinia recondita）に罹病したコムギを摩砕
して得た胞子懸濁液を噴霧接種し、22℃の湿室に
15時間保つた後、温室内水槽中に７日間放置し
た。評価は、各葉の病斑面積比率を査定し下記の
式により防除価を算出した。結果は表−８に示
す。
防除価（％）＝（無処理区の平均病斑面積比率
）−（処理区の平均病斑面積比率）／（無処理区の平均
斑面積比率）×100[Table] Test Example 4 Wheat Rust Control Efficacy Test A hydrating powder prepared in the same manner as in Test Example 1 was added to 1-2 leaf stage wheat (variety: Norin No. 61) grown in 6 cm diameter pots with water. It was diluted to a prescribed concentration and sprayed on foliage at a rate of 10 ml per pot. After air-drying the chemical solution,
Wheat infected with the wheat rust fungus Puccinia recondita was spray-inoculated with a spore suspension obtained by grinding, and placed in a humid room at 22°C.
After keeping it for 15 hours, it was left in a greenhouse aquarium for 7 days. For evaluation, the ratio of lesion area on each leaf was assessed and the control value was calculated using the following formula. The results are shown in Table-8. Control value (%) = (average lesion area ratio in untreated area) - (average lesion area ratio in treated area) / (average lesion area ratio in untreated area) x 100
【表】【table】
本発明の殺菌剤は薬剤感受性菌にも、薬剤耐性
菌にも強い殺菌効果を有する。
The bactericidal agent of the present invention has a strong bactericidal effect on both drug-susceptible and drug-resistant bacteria.
Claims (1)
トリフルオロメチル基を表わし、Ｒは低級アルキ
ル基またはハロゲン原子を表わし、ｎは１〜６の
整数を表わし、ｍは０または１の整数を表わす） で示されるピリジンカルボン酸アミド誘導体。 ２ 下記一般式（） （式中、Ｘはハロゲン原子、メチル基またはトリ
フルオロメチル基を表わし、Ｒは低級アルキル基
またはハロゲン原子を表わし、ｎは１〜６の整
数、ｍは０または１の整数を表わす） で示されるピリジンカルボン酸アミド誘導体を有
効成分として含有する農園芸用殺菌剤。[Claims] 1. The following general formula () (In the above formula, X represents a halogen atom, a methyl group or a trifluoromethyl group, R represents a lower alkyl group or a halogen atom, n represents an integer of 1 to 6, and m represents an integer of 0 or 1. ) Pyridinecarboxylic acid amide derivatives. 2 General formula below () (wherein, X represents a halogen atom, a methyl group or a trifluoromethyl group, R represents a lower alkyl group or a halogen atom, n represents an integer of 1 to 6, and m represents an integer of 0 or 1) An agricultural and horticultural fungicide containing a pyridinecarboxylic acid amide derivative as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19609487A JPS6434962A (en) | 1986-08-12 | 1987-08-05 | Pyridinecarboxylic acid amide derivative and agricultural and horticultural fungicide comprising said derivative as active ingredient |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18893686 | 1986-08-12 | ||
| JP19609487A JPS6434962A (en) | 1986-08-12 | 1987-08-05 | Pyridinecarboxylic acid amide derivative and agricultural and horticultural fungicide comprising said derivative as active ingredient |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6434962A JPS6434962A (en) | 1989-02-06 |
| JPH0362708B2 true JPH0362708B2 (en) | 1991-09-26 |
Family
ID=26505227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19609487A Granted JPS6434962A (en) | 1986-08-12 | 1987-08-05 | Pyridinecarboxylic acid amide derivative and agricultural and horticultural fungicide comprising said derivative as active ingredient |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6434962A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW464471B (en) * | 1997-12-18 | 2001-11-21 | Basf Ag | Fungicidal mixtures based on amide compounds and pyridine derivatives |
| JP3960677B2 (en) | 1998-02-16 | 2007-08-15 | 株式会社ニフコ | Stick-shaped object holder |
| US20080045546A1 (en) * | 2003-10-15 | 2008-02-21 | Axel Bouchon | Tetradydro-Naphthalene And Urea Derivatives |
| CN104768934B (en) * | 2012-05-09 | 2017-11-28 | 拜耳农作物科学股份公司 | Pyrazoles indanyl formamide |
| EP2935213B1 (en) * | 2012-12-19 | 2019-05-22 | Bayer CropScience Aktiengesellschaft | Difluoromethyl-nicotinic-indanyl carboxamides as fungicides |
| AR101820A1 (en) * | 2014-06-25 | 2017-01-18 | Bayer Cropscience Ag | DIFLUOROMETIL-INDANIL-CARBOXAMIDAS NICOTÍNICAS |
| TW202012372A (en) * | 2018-05-23 | 2020-04-01 | 德商拜耳廠股份有限公司 | Process for producing 2-(fluoroalkyl) nicotinic acids |
-
1987
- 1987-08-05 JP JP19609487A patent/JPS6434962A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6434962A (en) | 1989-02-06 |
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