JPH02172950A - Unsaturated aliphatic carboxylic acid derivative and fungicide - Google Patents
Unsaturated aliphatic carboxylic acid derivative and fungicideInfo
- Publication number
- JPH02172950A JPH02172950A JP32619888A JP32619888A JPH02172950A JP H02172950 A JPH02172950 A JP H02172950A JP 32619888 A JP32619888 A JP 32619888A JP 32619888 A JP32619888 A JP 32619888A JP H02172950 A JPH02172950 A JP H02172950A
- Authority
- JP
- Japan
- Prior art keywords
- methyl ester
- carboxylic acid
- acid methyl
- unsaturated aliphatic
- aliphatic carboxylic
- 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
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 title claims abstract description 11
- 230000000855 fungicidal effect Effects 0.000 title abstract description 8
- 239000000417 fungicide Substances 0.000 title abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000645 desinfectant Substances 0.000 claims 1
- -1 metal hydride compound Chemical class 0.000 abstract description 41
- 150000004702 methyl esters Chemical class 0.000 abstract description 21
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 11
- 239000002253 acid Substances 0.000 abstract description 11
- 235000009566 rice Nutrition 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract description 4
- 241000196324 Embryophyta Species 0.000 abstract description 3
- 239000003638 chemical reducing agent Substances 0.000 abstract description 3
- 150000002576 ketones Chemical class 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 230000003449 preventive effect Effects 0.000 abstract description 3
- 239000012279 sodium borohydride Substances 0.000 abstract description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract description 3
- 239000012448 Lithium borohydride Substances 0.000 abstract description 2
- 239000007868 Raney catalyst Substances 0.000 abstract description 2
- 229910000564 Raney nickel Inorganic materials 0.000 abstract description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract description 2
- 150000004678 hydrides Chemical class 0.000 abstract description 2
- 229910052742 iron Inorganic materials 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 229910052987 metal hydride Inorganic materials 0.000 abstract description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 abstract description 2
- 240000007594 Oryza sativa Species 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 241000209094 Oryza Species 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930182764 Polyoxin Natural products 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011388 polymer cement concrete Substances 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
【産業上の利用分野］
本発明は新規な不飽和脂肪族カルボン酸誘導体及びそれ
を合釘する農業用植物病害防除剤に関する。更に詳しく
は、稲いもち病防除剤に関する。
［従来技術］
従来より不飽和脂肪族カルボン酸誘導体の殺菌活性は知
られており、例えば特開昭５９−１４８７０６号公報に
はオクタデカトリエンカルボン酸オキサイド類が開示さ
れている。
［発明が解決しようとする課題］
しかしながら、従来の不飽和脂肪族カルボン酸誘導体は
殺菌活性が必ずしも十分でないという問題があった。
［問題点を解決するための手段］
本発明の目的は、殺菌剤として用いた場合に殺菌活性が
高くかつ作物に対する安全性の高い新規化合物、その製
造方法及びそれを有効成分とする殺菌剤をｃＪ洪するこ
とにある。
本発明者らは、鋭意研究の結果、特定の不飽和脂肪族カ
ルボン酸がきわめて優れた殺菌活性を存することを見い
だし本発明を完成した。
すなわち、本発明は
一般式［１１
％式％［１］
（ただし、Ｒは炭素数１〜３のアルキル入（を表わし、
ｍは５から９の整数を示し、ｎは２から６の整数を示す
。但し、ｍが７でありかつｎが４である場合を除く。）
で表わされる不飽和脂肪族カルボン酸誘導体、及び
一般式［１１で表わされる不飽和脂肪族カルボン酸誘導
体を有効成分として含有する農業用植物病害防除剤を提
供するものである。
［作用］
上述したように、本発明の不飽和脂肪族カルボン酸誘導
体は、上二己一般式［１］で示される。
紋穴［１１中、Ｒはメチル基、エチル基、プロピル基等
の炭素数１〜３のアルキル基を示し、ｍ１ｎは２から１
２の整数から選ばれる。ｍの好ましい例としては、５〜
９の整数であり、ｎの好ましい例としては２〜６の整数
である。但し、ｍが７でありかつｒｌが４である場合を
除く。
その様な具体的な例として以下のものを挙げることがで
きる。
（１）７−ヒトロキシテトラデカー８−エン−１０−イ
ンカルボン酸メチルエステル
（２）７−ヒトロキシベンタデカー８−エン−１０−イ
ンカルボン酸メチルエステル
（３）７−ヒドロキシへキサデカ−８−エン−１０−イ
ンカルボン酸メチルエステル
（４）７−ヒドロキシへブタデカ−８−エン−１０−イ
ンカルボン酸メチルエステル
（５）７−ヒトロキシオクタデカー８−エン−１０−イ
ンカルボン酸メチルエステル
（６）８−ヒドロキシベンタデカー９−エン−１１−イ
ンカルボン酸メチルエステル
（７）８−ヒドロキシへキサデカ−９−エン−１１−イ
ンカルボン酸メチルエステル
（８）８−ヒドロキシへブタデカ−９−エン−１１−イ
ンカルボン酸メチルエステル
（９）８−ヒドロキシオクタデカ−９−エン−１−イン
カルボン酸メチルエステル
（１０）８−ヒドロキシノナデカ−９−エン−１１−イ
ンカルボン酸メチルエステル
（１１）９−ヒドロキシへキサデカ−１０−エン−１２
−インカルボン酸メチルエステル（１２）９−ヒドロキ
シへブタデカ−１０−エン−１２−インカルボン酸メチ
ルエステル（１３）９−ヒドロキシノナデカ−１０−エ
ン−１２−インカルボン酸メチルエステル
（１４）９−ヒドロキシエイコサ−１０−エン−１２−
インカルボン酸メチルエステル
（１５）１０−ヒドロキシへブタデカ−１１−エン−１
３−インカルボン酸メチルエステル（１６）１０−ヒド
ロキシオクタデカ−１１−エン−１３−インカルボン酸
メチルエステル（１７）１０−ヒドロキシノナデカ−１
１−エン−１３−インカルボン酸メチルエステル（１ｇ
）１０−ヒドロキシエイコサ−１１−エン−１３−イン
カルボン酸メチルエステル（１９）１０−ヒドロキシヘ
ンエイコサ−１１−エン−１３−インカルボン酸メチル
エステル（２０）１１−ヒドロキシオクタデカ−１２−
エン−１４−インカルボン酸メチルエステル（２１）１
１−ヒドロキシノナデカ−１２−エン−１４−インカル
ボン酸メチルエステル（２２）１１−ヒドロキシエイコ
サ−１２−エン−１４−インカルボン酸メチルエステル
（２３）１１−、ヒドロキシヘンエイコサ−１２−エン
−１４−インカルボン酸メチルエステル（２４）１１−
ヒドロキシドコサ−１２−エン−１４−インカルボン酸
メチルエステル
本発明の不飽和脂肪族カルボン＃１誘導体は例えば以下
の式により製造することができる。
Ｈ
すなわち、−紋穴［１１］で表わされるケトン体を溶媒
荏在下あるいは無溶媒中、還元剤と反応させることによ
り製造できる。
溶媒としては、メタノール、エタノール、エーテル、テ
トラヒドロフラン、グライム、ジグライム等の極性溶媒
を挙げることができる。
還元剤としては、水素化ホウ素ナトリウム、水素化ホウ
素リチウム、水素化アルミニウムリチウム、水素化アル
キルスズ等の水素化金属化合物二佃鉛、鉄、ラネーニッ
ケル、パラジウムカーボン等の金属を挙げることができ
る。
この反応は、０℃〜１００℃で、５分〜２４時間反応さ
せることにより製造できる。好ましい温度範囲は、０℃
〜５０℃で、反応時間は、３０分〜１０時間である。
本発明化合物は、水田で発生するいもち病ことにはいも
ち防除に有用な予防薬であり、一方稲に対する薬害は実
質上記められなかった。
本発明化合物を稲いもち防除剤として用いる場合には、
他成分を加えずそのまま用いてもよいが、通常固体担体
、液体担体、界面活性剤その他の製剤補助剤と混合して
、乳剤、水和剤、懸濁剤、粒剤等に製剤する。
これらの製剤には存効成分として、本発明化合物を重量
比で０．１〜９９．９％、好ましくは１〜９９％含有す
る。
固体１０体には、カオリンクレー、アッタパルジャイト
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る。
液体担体には、キシレン、イソプロパツール、エチレン
グリコール、セルソルブ等のアルコール；アセトン、シ
キロヘキサノン、イソホロン等のケトン；ジメチルスル
オキシド、アセトニトリル、水等が挙げられる。
乳化、分散、ｌ展等のために用いられる界面活性剤には
、アルキル（アリール）スルホン酸塩、ジアルキルスル
ホコハク酸塩、ポリオキシエチレンアルキルアリールエ
ーテル燐酸エステル塩、アルキル硫酸エステル塩、ナフ
タレンスルポン酸ホルマリン縮合体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
ソルビクン脂肪酸エステル等の非イオン界面活性剤等が
挙げられる。
製剤補助剤としは、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、アラビアゴム、ＣＭＣ（カ
ルボキシメチルセルロース）、ＰＡＰ（酸性燐酸イソプ
ロピル）等が挙げられる。
本発明化合物は単独で使用できるが、たとえばチウラム
、ジチアノンバリダマイシンＡ１ポリオキシン、セロサ
イジン等の殺菌剤やマラソン、スミチオン、ＮＡＣ，Ｂ
ＰＭＣ等の殺虫剤、除草剤、肥料成分等と混合して農作
物に対する殺菌剤としての適用範囲の拡大を図りあるい
は、殺虫、除草または肥料の効果を合わせて発揮させる
こともできる。
［実施例］
以下、実施例により本発明をさらに詳しく説明するが、
本発明はこれらに限定されるものではない。
実施例１
７−ヒトロキシテトラデカー８−エン−１０−インカル
ボン酸メチルエステル（化合物番号ｌ）の製造
室温下、７−オキソテトラデカ−８−エン−１０−イン
カルボン酸メチルエステル０．５２ｇをメタノール１０
ｍ１に溶解させ、水素化ホウ素ナトリウム０．０７８ｇ
を加えて５分間反応させた。
含水アセトンを加えエーテル抽出、飽和食塩水で洗浄し
た後、無水硫酸マグネシウムで乾燥した。
エーテルを減圧留去し、残さをカラムクロマトグラフィ
ーにより精製し、目的物０．３５ｇを得た。
’Ｈ−ＮＭＲ（溶媒： ＣＤＣＩ ７１１位： δ
ｐｐｓ ）０．７０−１．９０（１，１３１１）、２．
００−２．４０（−，４＋１）、３．００−３．６０（
ｂｒ、 ｌ１ｌ） 、 ３．０ （ｓ、 ３１１） 、
３．７０−４．３０（＠、 １！り 、 ５．５０−
５．９５（＊、２１１）
Ｉ Ｒ３４００（ｂｒ）、２２００．１７３Ｑ、１７２
０ ｃｖａ″″Ｌ元素分析（％）：ｃ１５Ｈ２４ｏ３と
しテノ実測値 Ｃ，７１，６０，Ｈ，９，４６計算ｆｉ
Ｃ；７Ｌ ３９．Ｈ：９．５ｇ同様な方法により
得た本発明化合物の代表例とその物性を表１に示す。
実施例２（製剤）
シクロへキサノン５部とトキサノンＰ−８Ｌ（三洋化成
株式会社製乳化剤の商品名））１部よりなる溶液９５部
と本発明化合物（１）５部をはかりとり均一に混合し、
主剤含有量５％の乳剤を得た。
実施例３
稲いもち病に対する予防効果試験
ビニールカップ（直径１０ｃｍ 粒状培土；畑土−１
＝１）に栽培した４、０−４．５葉期の稲（品種：コシ
ヒカリ）をターンテーブル上に３カップ置き、実施例２
で製剤した乳剤の１００倍希釈溶液５０ｍ１をハンドス
プレーで散布した。薬液風乾後２５℃に設定した温室に
置き、約２０ｃｍ」−に稲いもち病罹病！１！１（Ｐｙ
ｒＬｃｕｌａｒｉａｏｒｙｚａｅ）を：ａ置して、４日
間静置した。
各カップごとに、第３．４本葉上の本病斑が各葉面積に
占める割合について下記要領で１カ・ｙブ当り１０茎（
２０茎）を調査し、式（１）、式（２）に従い発病度及
び防除価を求めた。
発病指数 発病面積率 注）
０拳・・０％
１ ・・・１０９６未満
２ ・・・１０％以上２５％未満
３ 嗜・−２５％以上５０％未満
４ Φ・−５０％以上
注）
調査葉面積に占める本病斑面積
防除価−
式（２）
防除価はＡ、Ｂ、Ｃ％Ｄの記号で表した。
Ａ・・・防除価 ９０〜１００％
Ｂ・・・防除価 ７０−９０％
Ｃ・・・防除価 ５０〜７０％
Ｄ・・・防除ｍｏ〜５０％
そのもＩｊ果を表２に示す。なお、稲に対する薬害は認
められなかった。
【発明の効果】
以上の説明から明らかなように、本発明の長鎖不飽和カ
ルボン酸：Ｊ、”９体は、稲いもち病に対し高いｒ防効
果を示し、稲いもち病から稲を保護する農業用殺菌剤と
して有用なものである。また、イネには、極めて安全に
使用できる安全性の高いものである。
特！「出願人
東ソー株式会社DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel unsaturated aliphatic carboxylic acid derivative and an agricultural plant disease control agent using the same. More specifically, it relates to a rice blast control agent. [Prior Art] The bactericidal activity of unsaturated aliphatic carboxylic acid derivatives has been known for a long time. For example, octadecatriene carboxylic acid oxides are disclosed in Japanese Patent Application Laid-Open No. 148706/1983. [Problems to be Solved by the Invention] However, conventional unsaturated aliphatic carboxylic acid derivatives have a problem in that their bactericidal activity is not necessarily sufficient. [Means for Solving the Problems] The object of the present invention is to provide a novel compound that has high fungicidal activity and high safety for crops when used as a fungicide, a method for producing the same, and a fungicide containing the same as an active ingredient. cJ Hong. As a result of intensive research, the present inventors discovered that a specific unsaturated aliphatic carboxylic acid has extremely excellent bactericidal activity, and completed the present invention. That is, the present invention is based on the general formula [11% formula% [1] (where R represents an alkyl group having 1 to 3 carbon atoms),
m represents an integer from 5 to 9, and n represents an integer from 2 to 6. However, this excludes the case where m is 7 and n is 4. )
The present invention provides an agricultural plant disease control agent containing an unsaturated aliphatic carboxylic acid derivative represented by the formula [11] and an unsaturated aliphatic carboxylic acid derivative represented by the general formula [11] as active ingredients. [Function] As described above, the unsaturated aliphatic carboxylic acid derivative of the present invention is represented by the general formula [1]. Monna [11, R represents an alkyl group having 1 to 3 carbon atoms such as methyl group, ethyl group, propyl group, m1n is 2 to 1
Selected from 2 integers. A preferable example of m is 5 to
It is an integer of 9, and a preferable example of n is an integer of 2 to 6. However, this excludes the case where m is 7 and rl is 4. The following can be mentioned as such specific examples. (1) 7-hydroxytetradecar 8-en-10-ynecarboxylic acid methyl ester (2) 7-hydroxybentadecar 8-en-10-ynecarboxylic acid methyl ester (3) 7-hydroxyhexadeca-8 -En-10-ynecarboxylic acid methyl ester (4) 7-Hydroxyhebutadec-8-ene-10-ynecarboxylic acid methyl ester (5) 7-Hydroxioctadecar-8-ene-10-ynecarboxylic acid methyl ester (6) 8-hydroxybentadec-9-en-11-ynecarboxylic acid methyl ester (7) 8-hydroxyhexadec-9-en-11-ynecarboxylic acid methyl ester (8) 8-hydroxyhebutadeca-9- En-11-ynecarboxylic acid methyl ester (9) 8-hydroxyoctadec-9-en-1-ynecarboxylic acid methyl ester (10) 8-hydroxynonadec-9-en-11-ynecarboxylic acid methyl ester ( 11) 9-hydroxyhexadec-10-ene-12
-ynecarboxylic acid methyl ester (12) 9-hydroxyhebutadec-10-en-12-ynecarboxylic acid methyl ester (13) 9-hydroxynonadec-10-en-12-ynecarboxylic acid methyl ester (14) 9 -Hydroxyeicosa-10-ene-12-
incarboxylic acid methyl ester (15) 10-hydroxyhebutadec-11-ene-1
3-ynecarboxylic acid methyl ester (16) 10-hydroxyoctadec-11-ene-13-ynecarboxylic acid methyl ester (17) 10-hydroxynonadeca-1
1-en-13-ynecarboxylic acid methyl ester (1g
) 10-hydroxyeicosa-11-en-13-ynecarboxylic acid methyl ester (19) 10-hydroxyeicosa-11-en-13-ynecarboxylic acid methyl ester (20) 11-hydroxyoctadec-12-
En-14-ynecarboxylic acid methyl ester (21) 1
1-hydroxynonadec-12-en-14-ynecarboxylic acid methyl ester (22) 11-hydroxyeicosa-12-en-14-ynecarboxylic acid methyl ester (23) 11-, hydroxyheneicosa-12- En-14-ynecarboxylic acid methyl ester (24) 11-
Hydroxydocos-12-en-14-ynecarboxylic acid methyl ester The unsaturated aliphatic carbon #1 derivative of the present invention can be produced, for example, by the following formula. H That is, it can be produced by reacting a ketone body represented by -Momonena [11] with a reducing agent in the presence of a solvent or in the absence of a solvent. Examples of the solvent include polar solvents such as methanol, ethanol, ether, tetrahydrofuran, glyme, and diglyme. Examples of the reducing agent include metal hydride compounds such as sodium borohydride, lithium borohydride, lithium aluminum hydride, and alkyltin hydride, metals such as iron, Raney nickel, and palladium carbon. This reaction can be produced by reacting at 0°C to 100°C for 5 minutes to 24 hours. The preferred temperature range is 0℃
At ˜50° C., reaction time is 30 minutes to 10 hours. The compound of the present invention is a useful preventive agent for controlling rice blast, especially rice blast, which occurs in rice fields, and on the other hand, virtually no chemical damage to rice was observed. When using the compound of the present invention as a rice blast control agent,
Although it may be used as it is without adding other ingredients, it is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to formulate emulsions, wettable powders, suspensions, granules, etc. These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 99.9%, preferably 1 to 99%. The 10 solids include kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite,
There are fine powders or granules such as talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Liquid carriers include alcohols such as xylene, isopropanol, ethylene glycol, and cellosolve; ketones such as acetone, cyclohexanone, and isophorone; dimethyl sulfoxide, acetonitrile, water, and the like. Surfactants used for emulsification, dispersion, expansion, etc. include alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, alkyl sulfate ester salts, and naphthalene sulfonic acid. Examples include anionic surfactants such as formalin condensates; nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene, and polyoxypropylene block copolymer sorbicun fatty acid esters. Examples of formulation aids include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate), and the like. The compound of the present invention can be used alone, but it can be used with fungicides such as thiuram, dithianonvalidamycin A1 polyoxin, cerocidin, Marathon, Sumithion, NAC, B.
It can be mixed with insecticides such as PMC, herbicides, fertilizer components, etc. to expand the scope of application as a fungicide to agricultural crops, or to exhibit the effects of insecticides, herbicides, or fertilizers in combination. [Examples] Hereinafter, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited to these. Example 1 Preparation of 7-hydroxytetradec-8-en-10-ynecarboxylic acid methyl ester (Compound No. 1) At room temperature, 0.52 g of 7-oxotetradec-8-en-10-ynecarboxylic acid methyl ester methanol 10
0.078 g of sodium borohydride dissolved in m1
was added and reacted for 5 minutes. After adding aqueous acetone and extracting with ether, washing with saturated brine, drying over anhydrous magnesium sulfate. The ether was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 0.35 g of the desired product. 'H-NMR (solvent: CDCI 711th position: δ
pps) 0.70-1.90 (1,1311), 2.
00-2.40(-,4+1), 3.00-3.60(
br, l1l), 3.0 (s, 311),
3.70-4.30 (@, 1!ri, 5.50-
5.95 (*, 211) I R3400 (br), 2200.173Q, 172
0 cva″″L elemental analysis (%): c15H24o3 and teno actual measurement C, 71, 60, H, 9, 46 calculation fi
C;7L 39. H: 9.5g Representative examples of the compounds of the present invention obtained by the same method and their physical properties are shown in Table 1. Example 2 (Formulation) 95 parts of a solution consisting of 5 parts of cyclohexanone and 1 part of toxanone P-8L (trade name of an emulsifier manufactured by Sanyo Kasei Co., Ltd.)) and 5 parts of the compound of the present invention (1) were weighed out and mixed uniformly. death,
An emulsion with a base agent content of 5% was obtained. Example 3 Preventive effect test against rice blast
Example 2
50 ml of a 100-fold diluted solution of the emulsion prepared above was sprayed by hand spray. After the chemical solution was air-dried, it was placed in a greenhouse set at 25℃, and about 20cm in length was infected with rice blast disease! 1!1(Py
rLculariaoryzae) was placed in a container and allowed to stand for 4 days. For each cup, calculate the proportion of main lesions on the 3rd and 4th true leaves to each leaf area by 10 stems per 1 cup (
20 stems), and the disease severity and control value were determined according to formulas (1) and (2). Disease index Disease area rate Note) 0 fist...0% 1...Less than 10962...10% or more and less than 25%3 Addiction--25% or more and less than 50%4 Φ--50% or moreNote) Survey leaf Control value of this lesion area in area - Formula (2) Control value was expressed by symbols A, B, C%D. A... Control value 90-100% B... Control value 70-90% C... Control value 50-70% D... Control mo~50% The results are shown in Table 2. In addition, no chemical damage to rice was observed. Effects of the Invention As is clear from the above explanation, the long-chain unsaturated carboxylic acid of the present invention: It is useful as an agricultural fungicide and can be used extremely safely on rice.Special!Applicant: Tosoh Corporation
Claims (2)
は５から９の整数を示し、ｎは２から６の整数を示す。 但し、ｍが７でありかつｎが４である場合を除く。）で
表わされる不飽和脂肪族カルボン酸誘導体。(1) General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼[I] (However, R represents an alkyl group with 1 to 3 carbon atoms, m
represents an integer from 5 to 9, and n represents an integer from 2 to 6. However, this excludes the case where m is 7 and n is 4. ) Unsaturated aliphatic carboxylic acid derivatives represented by
で表わされる不飽和脂肪族カルボン酸誘導体を有効成分
として含有する殺菌剤。(2) General formula [I] described in claim (1)
A disinfectant containing an unsaturated aliphatic carboxylic acid derivative represented by the following as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32619888A JPH02172950A (en) | 1988-12-26 | 1988-12-26 | Unsaturated aliphatic carboxylic acid derivative and fungicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32619888A JPH02172950A (en) | 1988-12-26 | 1988-12-26 | Unsaturated aliphatic carboxylic acid derivative and fungicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02172950A true JPH02172950A (en) | 1990-07-04 |
Family
ID=18185110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32619888A Pending JPH02172950A (en) | 1988-12-26 | 1988-12-26 | Unsaturated aliphatic carboxylic acid derivative and fungicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02172950A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6093681A (en) * | 1996-10-25 | 2000-07-25 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
-
1988
- 1988-12-26 JP JP32619888A patent/JPH02172950A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6093681A (en) * | 1996-10-25 | 2000-07-25 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
| US6093680A (en) * | 1996-10-25 | 2000-07-25 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
| US6184182B1 (en) | 1996-10-25 | 2001-02-06 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
| US6475953B1 (en) | 1996-10-25 | 2002-11-05 | Monsanto Technology Llc | Composition and method for treating plants with exogenous chemicals |
| US6479434B1 (en) | 1996-10-25 | 2002-11-12 | Monsanto Technology Llc | Composition and method for treating plants with exogenous chemicals |
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