JPH01117864A - Substituted nicotinic acid derivative, its production and agricultural and horticultural fungicide containing said derivative as active component - Google Patents
Substituted nicotinic acid derivative, its production and agricultural and horticultural fungicide containing said derivative as active componentInfo
- Publication number
- JPH01117864A JPH01117864A JP22767487A JP22767487A JPH01117864A JP H01117864 A JPH01117864 A JP H01117864A JP 22767487 A JP22767487 A JP 22767487A JP 22767487 A JP22767487 A JP 22767487A JP H01117864 A JPH01117864 A JP H01117864A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- nicotinic acid
- compound
- general formula
- 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
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 239000000417 fungicide Substances 0.000 title claims abstract description 11
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 238000007280 thionation reaction Methods 0.000 claims abstract description 6
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000004480 active ingredient Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 235000001968 nicotinic acid Nutrition 0.000 claims description 6
- 239000011664 nicotinic acid Substances 0.000 claims description 6
- 229960003512 nicotinic acid Drugs 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 43
- 238000002360 preparation method Methods 0.000 abstract description 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 2
- OIEQWZXDRGOGHA-UHFFFAOYSA-N 2,4-bis(methylsulfanyl)-2,4-bis(sulfanylidene)-1,3,2$l^{5},4$l^{5}-dithiadiphosphetane Chemical compound CSP1(=S)SP(=S)(SC)S1 OIEQWZXDRGOGHA-UHFFFAOYSA-N 0.000 abstract 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
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- 235000005152 nicotinamide Nutrition 0.000 abstract 1
- 239000011570 nicotinamide Substances 0.000 abstract 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical class C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 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 3
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- 229920001817 Agar Polymers 0.000 description 2
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- 229910000278 bentonite Inorganic materials 0.000 description 2
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- 238000009835 boiling Methods 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
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- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical class CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
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- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 244000000003 plant pathogen Species 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004577 thatch Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、置換ニコチン酸誘導体、その製造法およびそ
れを有効成分とする農−公用殺菌剤に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a substituted nicotinic acid derivative, a method for producing the same, and an agricultural/official fungicide containing the same as an active ingredient.
〈従来の技術〉
成る国のカルボン酸アニリド誌導体に殺菌活性が認めら
れることはＧ、 Ａ、 Ｗｈｉｔｅｓ ； Ｐｅｓｔｉ
ｃｉｄｅＢｉｏｃｈｅｍｉｓｔｒｙ ａｎｄ Ｐｈｙｓ
ｉｏｌｏｇ）ｒ １４ ＃ ２６ （１９８０）Ｊ、
Ｌ、 Ｈｕｐｐａｔｚ ； Ａｕ５ｔ、 Ｊ、 Ｃｈｅ
ｍ、、 １１Ｌ１８５（１９８３）、Ｂ、 Ｊａｎｋｓ
； Ｐｅ５ｔｉｃ、 Ｓｃｉ、、 Ｌ ４８（１９７
１）、特關昭５８−９６０６９号公報、ドイツ特許第２
６１ｉ６０１−Ａｔ号等の文献に記載されている。<Prior art> G. A. Whites; Pesti et al.
sideBiochemistry and Phys
ilog) r 14 #26 (1980) J,
L, Huppatz; Au5t, J, Che
m,, 11L185 (1983), B, Janks
; Pe5tic, Sci, L 48 (197
1), Special Publication No. 58-96069, German Patent No. 2
It is described in documents such as No. 61i601-At.
〈発明が解決しようとする問題点〉
しかしながら、これらの文献に例示されている化合物は
効力等の点で不充分であり、必ずしも満足すべきものと
は言い難く、かかる欠点の少ない薬剤の開発が望まれて
いる。<Problems to be solved by the invention> However, the compounds exemplified in these documents are insufficient in terms of efficacy, etc., and cannot be said to be necessarily satisfactory, and it is desirable to develop drugs with fewer such drawbacks. It is rare.
く問題点を解決するための手段〉
本発明者らは、このような状況に鑑み、優れた殺菌活性
を有する化合物を開発すべく極々検討した結果、下記一
般式［Ｉ］で示される置換ニコチンＭ誘導体、特にその
Ｉ換インダニルアミン誘導体が、上述のような欠点の少
ない優れた殺菌活性を有することを見出し、本発明に至
った。Means for Solving the Problems In view of the above circumstances, the present inventors have made extensive studies to develop a compound with excellent bactericidal activity, and as a result, the substituted nicotine represented by the following general formula [I] It has been found that M derivatives, particularly its I-substituted indanylamine derivatives, have excellent bactericidal activity with few of the above-mentioned drawbacks, leading to the present invention.
すなわち、本発明は、一般式
［式中、Ｒ’はメチル基、エチル基、ハロゲン原子、ト
リフルオロメチル基、ニトロ基、メトキシ基またはメチ
ルチオ基を表わし Ｒ１およびＲ１は同一または相異な
り水素原子またはメチル基を表わし、Ｘは酸素原子また
は硫黄原子を表わす。］
で示される置換ニコチン酸誘導体（以下、本発明化合物
と称する。）、その製造法およびそれを有効成分として
含有する農園芸用殺菌剤を提供するものである。That is, the present invention relates to the general formula [wherein R' represents a methyl group, an ethyl group, a halogen atom, a trifluoromethyl group, a nitro group, a methoxy group, or a methylthio group, and R1 and R1 are the same or different and are hydrogen atoms or It represents a methyl group, and X represents an oxygen atom or a sulfur atom. The present invention provides a substituted nicotinic acid derivative represented by (hereinafter referred to as the compound of the present invention), a method for producing the same, and an agricultural and horticultural fungicide containing the same as an active ingredient.
本発明化合物が優れた効力を有する植物病害としては、
たとえばイネの紋枯病（Ｒｈ１ｚｏｃｔｏｎｉａｓｏｌ
ａｎｉ ）、疑似紋枯病（Ｒｈ１ｚｏｃｔｏｎｉａ ｏ
ｒｙｚａｅ、 Ｒ。Plant diseases for which the compound of the present invention has excellent efficacy include:
For example, rice sheath blight (Rh1zoctoniasol)
ani), pseudosheath blight (Rh1zoctonia o
ryzae, R.
５ｏｌａｎｉ ｍ Ｂ型）、ムギ類のさび病（Ｐｕｃｃ
ｉｎｉａｓｔｒｉｉｆｏｒｍｉｓ、 Ｐ、 ｇｒａｍｉ
ｎｉａ、 Ｐ、 ｒｅｃｏｎｄｉｔａ、 Ｐ。5olani m type B), wheat rust (Pucc
iniastriiformis, P. grami
nia, P. recondita, P.
ｈｏｒｄｅｉ ）、雪腐病（Ｔｙｐｈｕｌａ １ｎｃａ
ｒｒａｔａ、 Ｔ。hordei), snow rot (Typhula 1nca)
rrata, T.
１ｓｈｉｋａｒｉｅｎｓｉｓ ）、裸黒穂病（Ｕｓｔｉ
ｌａｇｏ ｔｒｉｔｉｃｉ 。1shikariensis), naked smut (Usti
lago tritici.
Ｖ、 ｎｕｄａ）、各種作物の立枯病（Ｒｈ１ｚｏｃｔ
ｏｎｉａｓｏｌａｎｉ ）、白絹病（Ｃｏｒｔｉｃｉｕ
ｍｒｏｌｆｓｉｉ ）、ジャガイモ、ビートのりジフ
トニア病（Ｒｈ１ｚｏｃｔｏｎｉａａｏｌａｎｉ ）、
ナシの赤星病（Ｇｙｍｎｏｓｐｏｒａｎｇｉｕｍｈａｒ
ａｅａｎｕｍ ）、リンゴの黒星病（Ｖｅｎｔｕｒｉ
ａｉｎａｅｑｕａｒｉｇ ）、牧草、芝生等の葉腐病（
Ｒｈｉｚｏｃｔｏｎｉａ ５ｏｌａｎｉ ）、白絹病（
Ｃｏｒｔｉｃｉｕｍｒｏｌｆｓｉｌ）、菜さび病（ＩＪ
ｒｏｍｙｃｅｓＬｒｉｆｏｌｉｉ ）、雪腐病（Ｔｙｐ
ｈｕｌａ １ｎｃａｒｎａｔａ、 Ｔ、 １ｓｈｉｋａ
ｒｉｅｎｓｉｓ ）等が挙げられる。V, nuda), damping-off disease of various crops (Rh1zoct
oniasolani), white silk disease (Corticiu
mrolfsii), potato and beet diphtonia disease (Rh1zoctoniaaolani),
Gymnosporangiumhar
aeanum ), apple scab (Venturi
ainaequarig), leaf rot disease of grasses, lawns, etc. (
Rhizoctonia 5olani), white silk disease (
Corticium rolfsil), vegetable rust (IJ
romyces Lrifolii), snow rot (Typ.
hula 1ncarnata, T, 1shika
riensis), etc.
次に本発明化合物の製造法について詳しく説明する。Next, the method for producing the compound of the present invention will be explained in detail.
【製法（荀］
一般式［Ｉ］に於いて、Ｘが酸素原子を表わす化合物は
、例えば一般式
〔式中 Ｒ１およびＲ２は前記と同じ意味を表わす。〕
で示される置換ニコチン酸またはその反応性誘導体と一
般式
１式中、Ｒ１は前記と同じ意味を表わす。］で示される
置換アミノインダン誘導体とを反応させることによって
製造する仁とができる。[Manufacturing method (Xu)] In the general formula [I], the compound in which X represents an oxygen atom is, for example, a substituted nicotinic acid represented by the general formula [wherein R1 and R2 have the same meanings as above] or a reaction thereof. The derivative prepared by reacting the substituted aminoindan derivative with the substituted aminoindan derivative represented by the general formula 1, in which R1 has the same meaning as defined above, can be produced.
上記反応に於いて、溶媒は必ずしも必要ではないが、用
いられる溶媒としては、例えばベンゼン、トルエン、キ
シレン等の炭化水素類、クロルベンゼン、塩化メチレン
、クロロホルム、四塩化炭素等のハロゲン化炭化水素類
、ジイソプロピルエーテル、テトラヒドロフラン、ジオ
キサン等のエーテル類、アセトン、メチルエチルケトン
等のケトン類、酢酸エチル等のエステル類、アセトニト
リル等のニトリル類、ジメチルスルホキシド、ジメチル
ホルムアミド、水等であり、好ましくは、テトラヒドロ
フランが挙げられる。 ゛
上記反応に用いられる試剤の里は、一般式［ｍ］で示さ
れる置換アミノインダン誘導体１当盆に対して、一般式
［１１で示される置換ニコチン酸またはその反応性誘導
体は、０．４〜１．５当社、好ましくは、０．６〜１．
１当量の範囲である。In the above reaction, a solvent is not necessarily required, but examples of solvents that can be used include hydrocarbons such as benzene, toluene, and xylene, and halogenated hydrocarbons such as chlorobenzene, methylene chloride, chloroform, and carbon tetrachloride. , diisopropyl ether, tetrahydrofuran, dioxane, and other ketones; acetone, methyl ethyl ketone, and other ketones; ethyl acetate, and other esters; acetonitrile and other nitrites; dimethyl sulfoxide, dimethyl formamide, water, etc., with preference given to tetrahydrofuran. It will be done.゛The number of reagents used in the above reaction is 0.4 of the substituted nicotinic acid or its reactive derivative represented by the general formula [11] per 1 portion of the substituted aminoindan derivative represented by the general formula [m]. ~1.5 Our company, preferably 0.6~1.
It is in the range of 1 equivalent.
上記反応温度は任意にとりうるが通常０℃から反応液の
還流温度が好ましい。The above reaction temperature can be set arbitrarily, but it is usually preferably from 0°C to the reflux temperature of the reaction solution.
使用する一般式［Ｉ［］で示される［換ニコチン酸ある
いはその反応性誘導体としては、対応するカルボン酸、
酸無水物、酸塩化物、酸臭化物、カルボン酸エステル等
をあげることができ、使用する一般式［Ｉ］で示される
置換ニコチン酸あるいはその反応性誘導体に応じて適当
な反応助剤の存在下に反応させることができる。たとえ
ば、カルボン酸を使用する場合には、１−（８−ジメチ
ルアミノブロピル）−８−エチルカルボジイミドメチオ
ダイド、ジシクロへキシルカルボシイミド、五塩化リン
等が使用でき、またカルボン酸エステルを使用する場合
には、水素化ナトリウム、ナトリウムメチラート、ナト
リウムエチラート等が使用できる。さらに酸ハロゲン化
物または酸無水物を使用する場合には、水酸化ナトリウ
ム、水酸化カリウム、トリエチルアミン、Ｎ−メチルモ
ルホリン等を使用することができる。The substituted nicotinic acid or its reactive derivative represented by the general formula [I] to be used includes the corresponding carboxylic acid,
Examples include acid anhydrides, acid chlorides, acid bromides, carboxylic acid esters, etc., in the presence of an appropriate reaction aid depending on the substituted nicotinic acid represented by the general formula [I] used or its reactive derivative. can be reacted to. For example, when using a carboxylic acid, 1-(8-dimethylaminopropyl)-8-ethylcarbodiimidemethiodide, dicyclohexylcarbosiimide, phosphorus pentachloride, etc. can be used, and carboxylic acid esters can also be used. When used, sodium hydride, sodium methylate, sodium ethylate, etc. can be used. Furthermore, when using acid halides or acid anhydrides, sodium hydroxide, potassium hydroxide, triethylamine, N-methylmorpholine, etc. can be used.
これら反応助剤は通常触媒ユか６２当量の範囲で使用さ
れるが、好ましくは０．９５〜１．１当瓜で反応を行な
うことができる。These reaction aids are usually used in an amount of 62 equivalents per catalyst, but preferably 0.95 to 1.1 equivalents.
反応終了後は、反応助剤あるいはその反応生成物をろ過
あるいは水洗等により除去し、溶媒を留去すれば目的物
である置換ニコチン酸誘導体を得ることができ、ベンゼ
ン、トルエン、メタノール、エタノール、ジイソプロピ
ルエーテル、ヘキサン、クロロホルム等で再結晶するこ
とによりさらに精製することもできる。After the reaction is complete, the reaction aid or its reaction product is removed by filtration or washing with water, and the solvent is distilled off to obtain the desired substituted nicotinic acid derivative, which can be used to obtain benzene, toluene, methanol, ethanol, Further purification can be achieved by recrystallization from diisopropyl ether, hexane, chloroform, etc.
［製法（ｂ）〕
一般式［ｘｌに於いて、Ｘが硫黄原子を表わす化合物は
、Ｘが酸素原子を表わす化合物とチオノ化反応試薬とを
反応させることにより製造することができる。[Production method (b)] A compound in which X represents a sulfur atom in the general formula [xl] can be produced by reacting a compound in which X represents an oxygen atom with a thionation reaction reagent.
上記反応に用いられるチオノ化反応試薬としては、五−
比論、２．４−ビス（メチルチオ）−１，８，２，４−
ジテアジホスフエタン−２゜４−ジスルフィド、２，４
−ビス（ｐ−メトキシフェニル） −１ｍ ８ ｍ ２
＊ ４−ジテアジホスフエタンー２．４−ジスルフィ
ド等が挙げられる。The thionation reaction reagent used in the above reaction is
Ratio, 2.4-bis(methylthio)-1,8,2,4-
Ditheadiphosphethane-2゜4-disulfide, 2,4
-bis(p-methoxyphenyl) -1 m 8 m 2
* Examples include 4-ditheadiphosphethane-2,4-disulfide.
上記反応に於いて、反応溶媒は必ずしも必要ではないが
、一般的には、溶媒の存在下に行なわれる。In the above reaction, although a reaction solvent is not necessarily required, it is generally carried out in the presence of a solvent.
上記反応に用いられる試剤の量は、特に制限されるもの
ではないが、通常、一般式［Ｉ］に於いてＸが酸素原子
を表わす化合物１当愈に対しチオノ化反応試薬は、０．
５〜２０当鰍、好ましくは１〜１０当嵐の範囲である。The amount of the reagent used in the above reaction is not particularly limited, but usually, the amount of thionation reaction reagent is 0.1 to 1 equivalent of the compound in which X represents an oxygen atom in the general formula [I].
The range is from 5 to 20, preferably from 1 to 10.
上記反応は、溶媒の凝固点から沸点までの任意の温度、
好ましくは、０”Ｃから溶媒の沸点までの温度で行なう
ことができる・
反応終了後の反応液は、濃縮あるいは抽出し、水洗後、
必要に応じ再結晶等の操作に付すことにより目的物であ
る置換ニコチン酸日導体を得ることができる。The above reaction can be carried out at any temperature from the freezing point to the boiling point of the solvent.
Preferably, the reaction can be carried out at a temperature from 0"C to the boiling point of the solvent. After the reaction is complete, the reaction solution is concentrated or extracted, washed with water,
The desired substituted nicotinic acid conductor can be obtained by subjecting it to operations such as recrystallization, if necessary.
本発明化合物を殺菌剤の有効成分として用いる場合は、
他の何らの成分も加えずそのまま用いてもよいが、通常
は、固体担体、液体担体、界面活性剤その他の製剤用補
助剤と混合して、乳剤、水和剤、懸濁剤、粒剤、粉剤、
液剤等に製剤して用いる。When using the compound of the present invention as an active ingredient of a fungicide,
Although it may be used as is without adding any other ingredients, it is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to form emulsions, wettable powders, suspensions, and granules. , powder,
It is used by formulating it into a liquid formulation, etc.
これらの製剤には有効成分として本発明化合物を、重量
比で０．１〜９９．９％、好ましくは０．２〜８０％含
有する。These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 99.9%, preferably 0.2 to 80%.
固体担体としては、カオリンクレー、アブタパルジャイ
トクレー、ベントナイト、酸性白土、パイロフィライト
、タルク、珪藻土、方解石、トウモロコシ穂軸粉、クル
ミ殻粉、尿素、硫酸アンモニウム、合成含水酸化珪素等
の微粉末あるいは粒状物があげられ、液体担体としては
、キシレン、メチルナフタレン等の芳香族炭化水素類、
インプロパツール、エチレングリコール、セロソルブ等
のアルコール類、アセトン、シクロヘキサノン、イソホ
ロン等のケトン類、大豆油、綿実油等の植物油、ジメチ
ルスルホキシド、アセトニトリル、水尋があげられる。Solid carriers include fine powders such as kaolin clay, abtapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Alternatively, granules may be mentioned, and liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene,
Examples include alcohols such as Impropatol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, acetonitrile, and water hydroxide.
乳化、分散、湿辰等のために用いられる界面活性剤とし
ては、アルキル硫融エステル塩、アルキル（アリール）
スルキン酸塩、ジアルキルスルホこはく酸塩、ポリオキ
シエチレンアルキルアリールエーテルりん酸エステル坦
、ナフタレンスルホン戯本ルマリン縮合物等の陰イオン
界面活性剤、ポリオキシエチレンアルキルエーテル、ポ
リオキシエチレンポリオキシプロピレンブロックコボリ
マー、ソルビタン脂肪酸エステル、ポリオキシエチレン
ソルビタン脂肪酸エステル等の非イオン界面活性剤等が
あげられる。Surfactants used for emulsification, dispersion, wetting, etc. include alkyl sulfur ester salts, alkyl (aryl)
Anionic surfactants such as sulfinates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate esters, naphthalene sulfone lumaline condensates, polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block copolymer Examples include nonionic surfactants such as sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester.
製剤用補助剤としては、リグニンスルホン酸塩、アルギ
ン酸塩、ポリビニルアルコール、アラビアガム、ＣＭ、
Ｃ（カルボキシメチルセルロース）、ＰＡＰＩＩ性りん
酸インプロピル）等があげられる。As formulation aids, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CM,
C (carboxymethyl cellulose), PAPII (inpropyl phosphate), etc.
これらの製剤は、希釈せずそのまま、または例えば水で
希釈して植物体に直接施用するか、あるいは土壌に施用
する。These preparations are applied undiluted or, for example, diluted with water, directly to plants or to soil.
さらに詳しくは、上記製剤を植物体へ散布または散粉す
るか、土ｇ１表面へ散布、散粉または散粒するか、ある
いは必要に応じてその後さらに土壌と混和するなど穏々
の形態で使用できる。More specifically, the above-mentioned preparation can be used in a mild form, such as by being sprayed or powdered on the plant body, sprayed, powdered or granulated on the surface of the soil g1, or further mixed with the soil if necessary.
また、種子処理剤として用いる場合には、種子粉衣処理
、種子浸漬処理等して用いることができる。また、他の
殺菌剤と混合して用いることにより、殺菌効力の増強を
も期待できる。さらに、殺虫剤、殺ダニ剤、殺線虫剤、
除草剤、植物生長調節剤、肥料、土壌改良剤と混合して
用いることもできる。In addition, when used as a seed treatment agent, it can be used after seed coating treatment, seed soaking treatment, etc. Furthermore, by mixing it with other fungicides, it can be expected to increase the bactericidal efficacy. In addition, insecticides, acaricides, nematicides,
It can also be used in combination with herbicides, plant growth regulators, fertilizers, and soil conditioners.
なお、本発明化合物は、水田、畑地、果樹園、牧草地、
芝生地等の殺菌剤の有効成分として用いることができる
。The compound of the present invention can be used in rice fields, fields, orchards, pastures,
It can be used as an active ingredient in fungicides for lawns, etc.
本発明化合物を殺菌剤の有効成分として用いる場合、そ
の施用量は、気象条件、製剤形態、施用時期、方法、場
所、対象病害、対象作物等によっても異なるが、通詰１
アールあたり０．６１〜１００ Ｎ、好ましくは、１ｊ
Ｆ〜ｓｏｙであり、乳剤、水和剤、懸濁剤、液剤等を水
で希釈して施用する場合、その施用濃度は、ｏ、ｏｏｉ
％〜１％、好ましくは、０．００６％〜０．５％であり
、粒剤、粉剤等は、なんら希釈することなくそのまま施
用する。When the compound of the present invention is used as an active ingredient of a fungicide, the application amount varies depending on weather conditions, formulation form, application time, method, location, target disease, target crop, etc.
0.61 to 100 N per are, preferably 1j
F~soy, and when applying an emulsion, wettable powder, suspension, solution, etc. diluted with water, the application concentration is o, ooi
% to 1%, preferably 0.006% to 0.5%, and granules, powders, etc. are applied as they are without any dilution.
〈発明の効果〉
本発明化合物は、楓々の植物病原菌、特に担子ｌＩ類に
属する微生物による植物病害に対して卓効を示すことか
ら、殺菌剤の有効成分として種々の用途に用いることが
できる。<Effects of the Invention> The compound of the present invention is highly effective against plant diseases caused by plant pathogens of maple, especially microorganisms belonging to the Basidium class II, and therefore can be used for various purposes as an active ingredient of fungicides. .
〈実施例〉
以下に、本発明を製造例、製剤例および試験例によりさ
らに詳しく説明する。<Examples> The present invention will be explained in more detail below using production examples, formulation examples, and test examples.
まず、製造例を示す。First, a manufacturing example will be shown.
製造例１ （化合物ｌの合成）
ｔ、ｔ、８−）ジメチル−４−フミノインダン０．８０
１ （１，７ｍｍｏｌ ）オＪ：ヒヒ！Ｊ シン０、２
８ ｆ （８，５ｍｍｏｌ ）をテ）うｔ：ＦＣｌ２：
ｙン１Ｇｍｇに溶解させ、水冷下、内温６℃以下で攪拌
しながら、２−（）リフルオロメチル）ニコチン酸クロ
ライド０．８６ ｆ （１，７ｍｎ５ｏｌ ）をテトラ
ヒドロフラン８−＃ζ溶解させた液を滴下した。滴下後
、室温で一晩撹拌し、次いで水および酢酸エチルを加え
て抽出した。有機層は５％塩酸、水で洗浄した後、無水
硫酸ナトリウムで乾燥した。溶媒を留去して得られた結
晶をｎ−ヘキサンで洗浄、乾燥し、Ｎ−（１，１，８−
トリメチル−４−インダニル）−２−（トリフルオロメ
チル）ニコチン酸アミド０．４８Ｆを得た。（収率８０
％）。Production Example 1 (Synthesis of Compound 1) t,t,8-)dimethyl-4-fuminoindan 0.80
1 (1.7 mmol) OJ: Hee hee! J Shin 0, 2
8 f (8.5 mmol): FCl2:
A solution in which 0.86 f (1,7 mn5 ol) of 2-(lifluoromethyl)nicotinic acid chloride was dissolved in 8-#ζ of tetrahydrofuran while cooling with water and stirring at an internal temperature of 6°C or lower. was dripped. After the dropwise addition, the mixture was stirred at room temperature overnight, and then extracted with water and ethyl acetate. The organic layer was washed with 5% hydrochloric acid and water, and then dried over anhydrous sodium sulfate. The crystals obtained by distilling off the solvent were washed with n-hexane and dried to give N-(1,1,8-
Trimethyl-4-indanyl)-2-(trifluoromethyl)nicotinamide 0.48F was obtained. (Yield 80
%).
製造例２ （化合物４の合成）
２−ブロモニコチン酸０．２９１ （１，４２ｍｍｏｌ
）および１−（８−ジメチルアミノプロビル）に溶かし
、室温にて１時間攪拌した後、これＩＣ１、１、８−ト
リメチル−４−アミノインダン０．２５ ｆ （１，４
２ｍｍｏｌ ）を加え６時間還流下反応させた。次いで
反応液に塩化メチレンおよび水を加え抽出し、有機層を
濃縮後カラムクロマトグラフィー（ｉｉａ；ｎ−ヘキサ
ン：酢酸エチル＝５０：５０）で精製するξとにより、
Ｎ−（１，１，８−トリメチル−４−インダニル）−２
−ブロモニコチン酸アミド０．２０ ｙを得た（収率８
９９１； ）。Production Example 2 (Synthesis of Compound 4) 2-bromonicotinic acid 0.291 (1,42 mmol
) and 1-(8-dimethylaminopropyl) and stirred at room temperature for 1 hour.
2 mmol) was added thereto, and the mixture was reacted under reflux for 6 hours. Next, methylene chloride and water are added to the reaction solution for extraction, and the organic layer is concentrated and purified by column chromatography (IIA; n-hexane: ethyl acetate = 50:50).
N-(1,1,8-trimethyl-4-indanyl)-2
-0.20 y of bromonicotinic acid amide was obtained (yield: 8
991; ).
製造例８ （化合物５０合成）
２−メチルニコチン酸エチル２．００ダ（１２，１ｍｍ
ｏｌ ）および１，１．８−トリメチル−４−アミノイ
ンダン２．１２ ｆ （１２，１ｍｍｏｌ）をジメチル
スルホキシド２０−に溶解させ、これに室温にて攪拌下
６０％油性ηく累化ナトリウム０．４９１を添加した。Production Example 8 (Synthesis of Compound 50) Ethyl 2-methylnicotinate 2.00 Da (12.1 mm
ol) and 2.12 f (12.1 mmol) of 1,1.8-trimethyl-4-aminoindan are dissolved in 20-dimethylsulfoxide and 0.0% of accumulated sodium is added to the solution under stirring at room temperature. 491 was added.
その後、８０〜９０℃にて６時間撹拌した後、反応絞を
氷水にあけ酢酸エチルで抽出した。抽出液を水洗した後
濃縮し、得られた結晶をｎ−へキサンで洗浄し、Ｎ−（
１，１，８−トリメチル−４−インダニル）−２−メチ
ルニコチン酸アミドｓ、ｏｙを得た。（収率８４％）。Thereafter, after stirring at 80 to 90°C for 6 hours, the reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with water and concentrated, and the obtained crystals were washed with n-hexane and N-(
1,1,8-trimethyl-4-indanyl)-2-methylnicotinamide s,oy was obtained. (Yield 84%).
製造例４ （製法φ）による化合物（２８）の合成）Ｎ
−（１，１，’８−トリメチルー４−インダニル）−２
−メチルニコチン酸アミド０．５゜ｆおよび三硫化＠０
．１８Ｆとをトルエン１〇−にとかし還流下１０時間反
応させた。反応後、反応液を溌縮し、残渣をシリカゲル
をつめたカラムクロマトグラフィー（展開液；酢酸エチ
ル）Ｍζより処理しＮ−（１，１，８−トリメチル−４
−インダニル）−２−メチルニコチン酸チオアミド０．
８ Ｏｆを得た。（収率５７％）。Production Example 4 (Synthesis of compound (28) by production method φ) N
-(1,1,'8-trimethyl-4-indanyl)-2
-Methylnicotinamide 0.5°f and trisulfide @0
．． 18F was dissolved in 10- toluene and reacted under reflux for 10 hours. After the reaction, the reaction solution was compressed, and the residue was treated with column chromatography packed with silica gel (developing solution: ethyl acetate) Mζ to obtain N-(1,1,8-trimethyl-4
-indanyl)-2-methylnicotinic acid thioamide 0.
I got 8 Of. (Yield 57%).
＼、
＼
゛へ、
＼１、 １
゛・１、□
゛へ、
＼、
上記のような製造法によって製造できる本発明化合物の
いくつかを第１表に示す。\, \ ゛, \1, 1 ゛・1, □ ゛, \, Table 1 shows some of the compounds of the present invention that can be produced by the above production method.
第 １ 表
一般式
で示される化合物
次に製剤例を示す。なお、本発明化合物は第１表の化合
物番号で示す。部はＭｆｊｋ部である。Table 1 Compounds represented by the general formula Next, formulation examples are shown. The compounds of the present invention are indicated by compound numbers in Table 1. The part is the Mfjk part.
製剤例１
本発明化合物（１）〜（２４）の各々５０部、リグニン
スルホン酸カルシウム８部、ラウリル硫酸ナトリウム２
部および合成含水酸化珪素４５部をよく粉砕混合して有
効成分５０％の永和剤各々を得る。Formulation Example 1 50 parts each of the compounds (1) to (24) of the present invention, 8 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate
1 part and 45 parts of synthetic hydrated silicon oxide are thoroughly ground and mixed to obtain each permanent agent containing 50% of the active ingredient.
製剤例２
本発明化合物（１）〜（２４）の各々１０部、ポリオキ
シエチレンスチリルフェニルエーテル１４部、ドデシル
ベンゼンスルホン酸カルシウム６部、キシレン７０部を
よく混合して有効成分１０％の乳剤各々を得る。
″製剤例８
本発明化合物（１）〜（２４）の各々２部、合成含水酸
化珪ｇｔｉ、リグニンスルホン酸カルシウム２部、ベン
トナイト８０部およびカオリンクレー６５部をよく粉砕
混合し、水を加えてよく練り合せた後、造粒乾燥して有
効成分２％の粒剤各々を得る。Formulation Example 2 10 parts each of the compounds (1) to (24) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 70 parts of xylene were thoroughly mixed to form an emulsion containing 10% active ingredient. get.
``Formulation Example 8 2 parts each of the compounds (1) to (24) of the present invention, synthetic hydrated silica gti, 2 parts of calcium lignosulfonate, 80 parts of bentonite and 65 parts of kaolin clay were thoroughly ground and mixed, and water was added. After thoroughly kneading, the mixture is granulated and dried to obtain granules each containing 2% of the active ingredient.
製剤例４
本発明化合物（１） ヘ（２４）の各々２５部、ポリオ
キシエチレンソルビタンモノオレエート８部、ＣＭ、Ｃ
８部、水６９部を混合し、粒度が５ミクロン以下になる
まで湿式粉砕して有効成分２６％の懸濁剤各々を得る。Formulation Example 4 25 parts each of compounds of the present invention (1) (24), 8 parts of polyoxyethylene sorbitan monooleate, CM, C
8 parts and 69 parts of water are mixed and wet milled until the particle size is less than 5 microns to obtain suspensions each containing 26% active ingredient.
製剤例５
本発明化合物（１）〜（２４）の各々２部、カオリンク
レー８８部およびタルク１０部をよく粉砕混合して有効
成分２％の粉剤各々を得る。Formulation Example 5 Two parts of each of the compounds (1) to (24) of the present invention, 88 parts of kaolin clay and 10 parts of talc are thoroughly ground and mixed to obtain powders each containing 2% of the active ingredient.
製剤例６
本発明化合物（１）〜（２４）の各々１０部、ポリオキ
シエチレンスチリルフェニルエーテル１部、水８９部を
混合し、有効成分１０９６の液剤各々を得る。Formulation Example 6 10 parts each of the compounds (1) to (24) of the present invention, 1 part polyoxyethylene styrylphenyl ether, and 89 parts water are mixed to obtain each liquid preparation of active ingredient 1096.
次に本発明化合物が殺菌剤の有効成分として有用である
ことを試験例で示す。なお、本発明化合物は、第１表の
化合物番号で示し、比較対照に用いた化合物は第２表の
化合物記号で示す。Next, test examples will show that the compounds of the present invention are useful as active ingredients of fungicides. The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols in Table 2.
第２表
また防除効力は、調葺時の供試植物の発病状態すなわち
葉、茎等の菌叢、病斑の程度を肉眼観察し、菌叢、病斑
が全く認められなければ「５」、１０部程度認めれば「
４」、８０部程度認めれば［８Ｊ、５０部程度認めれば
「２」、７０部程度認めれば「１」、それ以上で化合物
を供試していない場合の発病状態と差が認められなけれ
ば「０」として、θ〜６の６段階に評価し、０．１．２
．８．４．５で示す。Table 2: The pesticidal efficacy is determined by visually observing the disease state of the test plants at the time of thatch preparation, i.e., the degree of bacterial flora and lesions on leaves, stems, etc., and if no bacterial flora or lesions are observed, the rating is 5. , if you recognize about 10 copies,
4", if about 80 parts are detected [8J, if about 50 parts are detected, it is "2", if about 70 parts are detected, it is "1", and if there is no difference from the disease onset state when no compound is tested at more than 50 parts, "0", evaluated in 6 stages from θ to 6, 0.1.2
．． 8.4.5.
試験例１ イネ紋枯病予防効果試験
プラスチックポットに砂壌土を詰め、イネ（近畿８８号
）を播葛シ・、温室内で６０日間育成した。６〜７葉が
展開したイネの動画に、製剤例２に準じて乳剤にした供
試化合物を、水で希釈して所定濃度にし、それを葉面に
充分付着するように茎葉散布した。散布４時間後、イネ
紋枯病菌の含菌寒天片を貼付接種した。接種後２８℃、
多湿下で４日間育成し、防除効力を調査した。その結果
を第３表に示す。Test Example 1 Test for Preventive Effect on Rice Sheath Blight A plastic pot was filled with sandy loam, and rice (Kinki No. 88) was grown in a greenhouse for 60 days. A test compound made into an emulsion according to Formulation Example 2 was diluted with water to a predetermined concentration and sprayed on the foliage so that it would sufficiently adhere to the leaf surface on a video of a rice plant with 6 to 7 leaves developed. Four hours after the spraying, agar pieces containing the rice sheath blight fungus were pasted and inoculated. 28℃ after inoculation,
The plants were grown for 4 days in a humid environment and their pesticidal efficacy was investigated. The results are shown in Table 3.
第 ８ 表
試験例２ イネ紋枯病浸透移行効果試験１８０−容のプ
ラスチックポットに砂壌土を詰め、イネ（近畿８８号）
を帰属し、温室内で８週間育成した。６〜７葉が展間し
たイネに、製剤例１に準じて水和剤にした供試化合物を
、水で希釈し、その所定量を土壌に潅注ａ７日間温室内
で育成し、イネ紋枯病菌含菌寒天片を貼付接種した。接
汎後２８℃、多湿下で４日間育成し、防除効力を調査し
た。Table 8 Test Example 2 Rice sheath blight penetration and transfer effect test A 180-volume plastic pot was filled with sandy loam, and rice (Kinki No. 88) was grown.
was assigned and grown in a greenhouse for 8 weeks. A test compound prepared as a hydrating powder according to Formulation Example 1 was diluted with water to a rice plant with 6 to 7 leaves, and the specified amount was sprinkled on the soil. Agar pieces containing disease bacteria were pasted and inoculated. After inoculation, the plants were grown for 4 days at 28°C under high humidity, and their pesticidal efficacy was investigated.
その結果を第４表に示す。The results are shown in Table 4.
第 ４ 表
試験例８ インゲン白絹病予防効果試験２５〇−容プラ
スチックポットにあらかじめふすま培地で培養した白絹
病原菌を砂壌土とよく混合し詰めた。その上にインゲン
（大正金時）を播種した。製剤例１に準じて水和剤にし
た供試化合物を水で希釈し、その所定量を土壌に１注し
た。１産後８週間温室内で育成し、地際部の茎の発病程
度により防除効力を調査した。その結果を第５表に示す
。Table 4 Test Example 8 Preventive Effect Test on French Bean White Silk Disease The white silk pathogenic bacteria, which had been cultured in advance in a bran medium, was thoroughly mixed with sandy loam and packed into a 250-capacity plastic pot. On top of that, green beans (Taisho Kintoki) were sown. A test compound made into a hydrating powder according to Formulation Example 1 was diluted with water, and a predetermined amount of the compound was poured into soil. After the first birth, the plants were grown in a greenhouse for 8 weeks, and the control efficacy was investigated based on the degree of disease onset on the stems at the ground level. The results are shown in Table 5.
第 ６ 表
試験例４ コムギ裸黒穂病種子処理試験製剤例１に準じ
て水和剤にした供試化合物を、水で希釈して所定濃度に
し、その薬液にコムギ裸黒穂病菌（Ｕｓｔｉｌａｇｏ
ｔｒｉｔｉｃｉ ）を接種感染させたコムギ稲子（農林
６１号）を入れ、２４時間浸漬処理した。その後、圃場
に播覆して栽培し、出穂後に穂の発病状態により防除効
力を調査した。その結果を第６表に示す。Table 6 Test Example 4 Wheat Bare Smut Seed Treatment Test A test compound made into a wettable powder according to Preparation Example 1 was diluted with water to a predetermined concentration, and the chemical solution was added to the wheat bare smut fungus (Ustilago).
Wheat rice seedlings (Norin No. 61) inoculated and infected with P. tritici were added and soaked for 24 hours. Thereafter, the seeds were sown in the field and cultivated, and after earing, the control efficacy was investigated based on the disease state of the ears. The results are shown in Table 6.
第 ６ 表
試験例５ コムギ赤さび病治療効果試験プラスチックポ
ットに砂壌土を詰め、コムギ（農林７８号）を播種し、
温室内で１０日間育成した。第２〜８葉が展開したコム
ギの幼苗にコムギ赤さび７ｉ３！菌の胞子を接種ｉノだ
。Table 6 Test Example 5 Wheat Rust Treatment Efficacy Test A plastic pot was filled with sandy loam and wheat (Norin No. 78) was sown.
It was grown in a greenhouse for 10 days. Wheat rust 7i3 on wheat seedlings with 2nd to 8th leaves developed! It is inoculated with bacterial spores.
接種後２８℃多湿下で１日育成し、製剤例２に準じて乳
剤にした供試化合物を、水で希釈して所定濃度にし、そ
れを麺面番ζ充分付着するように茎葉散布した。散布ｆ
＆２３℃照明下で照明量育成し、防除効力を調査したう
その結果を第７表に示す。After inoculation, the test compound was grown in a humid environment at 28° C. for one day, and an emulsion prepared according to Formulation Example 2 was diluted with water to a predetermined concentration and sprayed on the foliage so that the noodle surface number ζ was sufficiently adhered. Spreading f
Table 7 shows the results of cultivating under illumination at +23°C and investigating the control efficacy.
Claims (5)
トリフルオロメチル基、ニトロ基、メトキシ基またはメ
チルチオ基を表わし、 Ｒ＾２およびＲ＾３は同一または相異なり水素原子また
はメチル基を表わし、Ｘは酸素原子または硫黄原子を表
わす。］ で示される置換ニコチン酸誘導体。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 is a methyl group, ethyl group, halogen atom,
It represents a trifluoromethyl group, a nitro group, a methoxy group or a methylthio group, R^2 and R^3 are the same or different and represent a hydrogen atom or a methyl group, and X represents an oxygen atom or a sulfur atom. ] A substituted nicotinic acid derivative represented by:
トリフルオロメチル基、ニトロ基、メトキシ基またはメ
チルチオ基を表わし、 Ｒ＾２は水素原子またはメチル基を表わす。］で示され
る置換ニコチン酸またはその反応性誘導体と一般式 ▲数式、化学式、表等があります▼ ［式中、Ｒ＾３は水素原子またはメチル基を表わす。］ で示される置換アミノインダン誘導体とを反応させるこ
とを特徴とする一般式 ▲数式、化学式、表等があります▼ ［式中、Ｒ＾１、Ｒ＾２およびＲ＾３は前記と同じ意味
を表わす。］ で示される置換ニコチン酸誘導体の製造法。(2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 is a methyl group, ethyl group, halogen atom,
It represents a trifluoromethyl group, a nitro group, a methoxy group or a methylthio group, and R^2 represents a hydrogen atom or a methyl group. ] Substituted nicotinic acid or its reactive derivatives and the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^3 represents a hydrogen atom or a methyl group. ] General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1, R^2 and R^3 have the same meanings as above. represent. ] A method for producing a substituted nicotinic acid derivative.
トリフルオロメチル基、ニトロ基、メトキシ基またはメ
チルチオ基を表わし、 Ｒ＾２およびＲ＾３は同一または相異なり水素原子また
はメチル基を表わす。］ で示される置換ニコチン酸誘導体をチオノ化反応試薬と
反応させることを特徴とする一般式 ▲数式、化学式、表等があります▼ ［式中、Ｒ＾１、Ｒ＾２およびＲ＾３は前記と同じ意味
を表わす。］ で示される置換ニコチン酸誘導体の製造法。(3) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 is a methyl group, ethyl group, halogen atom,
It represents a trifluoromethyl group, a nitro group, a methoxy group or a methylthio group, and R^2 and R^3 are the same or different and represent a hydrogen atom or a methyl group. ] A general formula characterized by reacting a substituted nicotinic acid derivative represented by the following with a thionation reaction reagent ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1, R^2 and R^3 are the above-mentioned expresses the same meaning as ] A method for producing a substituted nicotinic acid derivative.
チルチオ）−１，３，２，４−ジチアジホスフエタン−
２，４−ジスルフィドまたは２，４−ビス（ｐ−メトキ
シフェニル）−１，３，２，４−ジチアジホスフエタン
−２，４−ジスルフィドである特許請求の範囲第３項記
載の製造法。(4) The thionation reaction reagent is phosphorus pentasulfide, 2,4-bis(methylthio)-1,3,2,4-dithiadiphosphethane-
4. The manufacturing method according to claim 3, which is 2,4-disulfide or 2,4-bis(p-methoxyphenyl)-1,3,2,4-dithiadiphosphethane-2,4-disulfide.
リフルオロメチル基、ニトロ基、メトキシ基またはメチ
ルチオ基を表わし、 Ｒ＾２およびＲ＾３は同一または相異なり水素原子また
はメチル基を表わし、Ｘは酸素原子 または硫黄原子を表わす。］ で示される置換ニコチン酸誘導体を有効成分として含有
することを特徴とする農園芸用殺菌剤。(5) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 represents a methyl group, ethyl group, halogen atom trifluoromethyl group, nitro group, methoxy group, or methylthio group, and R^2 and R^3 are the same or different and represent a hydrogen atom or a methyl group, and X represents an oxygen atom or a sulfur atom. ] An agricultural and horticultural fungicide characterized by containing a substituted nicotinic acid derivative represented by the following as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22767487A JPH01117864A (en) | 1987-07-02 | 1987-09-10 | Substituted nicotinic acid derivative, its production and agricultural and horticultural fungicide containing said derivative as active component |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62-167528 | 1987-07-02 | ||
| JP16752887 | 1987-07-02 | ||
| JP22767487A JPH01117864A (en) | 1987-07-02 | 1987-09-10 | Substituted nicotinic acid derivative, its production and agricultural and horticultural fungicide containing said derivative as active component |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01117864A true JPH01117864A (en) | 1989-05-10 |
Family
ID=26491540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22767487A Pending JPH01117864A (en) | 1987-07-02 | 1987-09-10 | Substituted nicotinic acid derivative, its production and agricultural and horticultural fungicide containing said derivative as active component |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01117864A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7598395B2 (en) | 2002-10-18 | 2009-10-06 | Syngenta Crop Protection, Inc. | Heterocyclocarboxamide derivatives |
| WO2012084812A1 (en) | 2010-12-20 | 2012-06-28 | Isagro Ricerca S.R.L. | Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions |
| JP2017522290A (en) * | 2014-06-25 | 2017-08-10 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | Difluoromethyl-nicotinic acid-indanyl carboxamides |
| US10143200B2 (en) | 2012-06-15 | 2018-12-04 | Stichting I-F Product Collaboration | Synergistic compositions for the protection of agrarian crops and the use thereof |
-
1987
- 1987-09-10 JP JP22767487A patent/JPH01117864A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7598395B2 (en) | 2002-10-18 | 2009-10-06 | Syngenta Crop Protection, Inc. | Heterocyclocarboxamide derivatives |
| US7994093B2 (en) | 2002-10-18 | 2011-08-09 | Syngenta Crop Protection, Inc. | Heterocyclocarboxamide derivatives |
| WO2012084812A1 (en) | 2010-12-20 | 2012-06-28 | Isagro Ricerca S.R.L. | Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions |
| EP2944629A1 (en) | 2010-12-20 | 2015-11-18 | Stichting I-F Product Collaboration | Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions |
| US9192160B2 (en) | 2010-12-20 | 2015-11-24 | Stichting I-F Product Collaboration | Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions |
| US10143200B2 (en) | 2012-06-15 | 2018-12-04 | Stichting I-F Product Collaboration | Synergistic compositions for the protection of agrarian crops and the use thereof |
| JP2017522290A (en) * | 2014-06-25 | 2017-08-10 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | Difluoromethyl-nicotinic acid-indanyl carboxamides |
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