JPH02172951A - Plant blight controlling agent - Google Patents
Plant blight controlling agentInfo
- Publication number
- JPH02172951A JPH02172951A JP32619788A JP32619788A JPH02172951A JP H02172951 A JPH02172951 A JP H02172951A JP 32619788 A JP32619788 A JP 32619788A JP 32619788 A JP32619788 A JP 32619788A JP H02172951 A JPH02172951 A JP H02172951A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- methyl ester
- acid methyl
- formula
- ynecarboxylic
- 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 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000645 desinfectant Substances 0.000 claims description 2
- -1 metal hydride compound Chemical class 0.000 abstract description 50
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 15
- 150000004702 methyl esters Chemical class 0.000 abstract description 15
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 13
- 235000009566 rice Nutrition 0.000 abstract description 13
- 239000002253 acid Substances 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 230000000855 fungicidal effect Effects 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 239000000417 fungicide Substances 0.000 abstract description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 3
- 230000003449 preventive effect Effects 0.000 abstract description 3
- 241000196324 Embryophyta Species 0.000 abstract description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000463 material Substances 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
- 229910000104 sodium hydride Inorganic materials 0.000 abstract description 2
- 239000012312 sodium hydride Substances 0.000 abstract description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 abstract 1
- 240000007594 Oryza sativa Species 0.000 abstract 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 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 1
- 241000209094 Oryza Species 0.000 description 12
- 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
- 239000000243 solution Substances 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 230000000694 effects Effects 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
- 239000000843 powder Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 239000008112 carboxymethyl-cellulose Substances 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
- 238000000034 method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000005764 Dithianon Substances 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
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 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
- 231100000674 Phytotoxicity Toxicity 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
- 241000607479 Yersinia pestis Species 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
- 230000002378 acidificating effect Effects 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
- 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
- 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
- UOKRBSXOBUKDGE-UHFFFAOYSA-N butylphosphonic acid Chemical compound CCCCP(O)(O)=O UOKRBSXOBUKDGE-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 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
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- 230000002363 herbicidal effect Effects 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
- 238000005304 joining Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 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
- 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
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 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
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000010902 straw 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
- 150000003512 tertiary amines Chemical class 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
- 239000008096 xylene Substances 0.000 description 1
Abstract
Description
［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
を含有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。
ｒ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５９−１４Ｊ１７０６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。
［課題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提倶すること
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有することを見い
だし本発明を完成した。
すなわち、本発明は
−紋穴［１］
Ｏ［！］
（ただし、Ｒは炭素数１〜３のアルキル基を表わし、Ｉ
ｌｌは５から９の整数を示し、ｎは２から６の整数を示
す。）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。[Industrial Application Field] The present invention relates to a novel unsaturated aliphatic carboxylic acid derivative and an agricultural plant disease control agent containing 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, and for example, octadecatrienecarboxylic acid oxides are disclosed in Japanese Patent Application Laid-Open No. 59-14J1706. [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] An object of the present invention is to provide a novel compound that has high fungicidal activity and is highly safe for crops when used as a fungicide, a method for producing the same, and a fungicide containing the same as an active ingredient. It's about joining together. 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 - Monana [1] O[! ] (However, R represents an alkyl group having 1 to 3 carbon atoms, and I
ll represents an integer from 5 to 9, and n represents an integer from 2 to 6. ) and an unsaturated aliphatic carboxylic acid derivative represented by the general formula [11] as active ingredients.
【作用］
に述したように、本発明の不飽和脂肪族カルボン酸誘導
体は、１：、記−紋穴［１］で示される。−紋穴［１］
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１２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〜Ｂの整数である。
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−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
（２）７−オキソベン−デカー８−二ンー１０−インカ
ルボン酸メチルエステル
（３）７−オキソヘキサデカ−８−エン−１０−インカ
ルボン酸メチルエステル
（４）７−オキツヘブタデカー８−エン−１０−インカ
ルボン酸メチルエステル
（５）７−オキソオクタデカ−８−エン−１０−インカ
ルボン酸メチルエステル
（６）８−オキソベンタデカー９−エン−１１−インカ
ルボン酸メチルエステル
（７）８−オキソヘキサデカ−９−エン−１１−インカ
ルボン酸メチルエステル
（８）８−オキソヘプタデカ−９−エン−１１−インカ
ルボン酸メチルエステル
（９）８−オキソオクタデカ−９−エン−１１−インカ
ルボン酸メチルエステル
（１０）８−オキソノナデカ−９−エン−１１＝インカ
ルボン酸メチルエステル
（１１）９−オキソヘキサデカ−１０−エン−１２−イ
ンカルボン酸メチルエステル
［２）９−オキソヘプタデカ−１０−エン−１２−イン
カルボン酸メチルエステル
（１３）９−オキソオクタデカ−１０−エン−１２−イ
ンカルボン酸メチルエステル
（１４）９−オキソノナデカ−１０−エン−１２−イン
カルボン酸メチルエステル
（１５）９−オキソエイコサ−１０−エン−１２−イン
カルボン酸メチルエステル
（１６）１０−オキソヘプタデカ−１１−エン−１３−
インカルボン酸メチルエステル
（１７）１０−オキソオクタデカ−１１−エン−１３−
インカルボン酸メチルエステル
（１ｇ）１０−オキソノナデカ−１１−エン−１３−イ
ンカルボン酸メチルエステル
（１９）１０−オキソエイコサ−エニーエン−１３−イ
ンカルボン酸メチルエステル
（２０）１０−オキソヘンエイコサ−１１−エン−１３
−インカルボン酸メチルエステル（２ヱ） １１−オキ
ソオクタデカ−１２−エン−１４−インカルボン酸メチ
ルエステル
（２２）１１−オキソノナデカ−１２−エン−１４−イ
ンカルボン酸メチルエステル
（２３）１１−オキソエイコサ−１２−エン−１４−イ
ンカルボン酸メチルエステル
（２４）１１−オキソヘンエイコサ−１２−エン−１４
−インカルボン酸メチルエステル（２５）１１−オキソ
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酸誘導体は例えば以下の
式により製造することができる。
［１１
［ｍ］
すなわち、−紋穴［■］で表わされるホスホネート体と
一般式［Ｉ［Ｉ］で表わされるアルダ４１体を溶媒存在
下あるいは無溶媒中、塩μ存在下反応させることにより
製造できる。
溶媒としては、アセトニトリル、グライム、テトラヒド
ロフラン、ジオキサン、Ｎ、Ｎ−ジメチルホルムアミド
等の極性溶媒を挙げることができる。塩基としては、１
．８−ジアザビシクロ［５゜４．０１−７−ウンデセン
、１．８−ジアザビシクロ［２，２，２１オクタン、ト
リエチルアミン等の第三級アミン；水素化ナトリウム、
水素化カリウム等の水素化金属化合物；ブチルリチウム
等のアルキル金属等を挙げることができる。
この反応は、θ℃〜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Ｇｍな予防薬であり、一方稲に対する薬害は実
質４−認められなかった。
本発明化合物を補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１１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１〜９９％含有す
る。
固体ｔｔ−を体には、カオリンクレー、アッタバルジャ
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、トウモロコシ穂軸扮、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；ア七トン、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、温域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
タレンスルホ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ツクコポリマー
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ｈｌｉ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） 、ＰＡ
Ｐ （酸性燐酸イソプロピル）等が挙げられる。
本発明化合物は？；１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ジンＡ５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
，ＢＰＭＣ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−オキソテン−デカ−８−二ンー１０−インカルボン
酸メチルエステル（化合物番号１）の製造
窒素気流中、無水塩化リチウム０．１４ｇのアセトニト
リル３０ｍ１懸濁液に、ジメチル ２−オキソ−７−メ
ドキシカルポニルへブチルホスホナート０．６２ｇを室
温上滴下した。その後、１゜８−ジアザビシクロ［５，
４，０１−７−ウンデセン０．４６ｇのアセトニトリル
溶液、２−オクテン−４−イナール０．５０ｇのアセト
ニトリル溶液を順次滴下し、４５分間撹拌した。反応液
にエーテル１００ｍ１を加えて濾過し、エーテル相を３
％塩酸、飽和重酋水、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
．５２ｇ （ｏｉ １）を得た。
’Ｈ−ＮＭＲ（溶媒： ＣＤＣＩ 単位：δｐｐｍ
）０．７０−２．００（嘗、ＩＬＪり、２．００−２
．７０（ｍ、０１１）、３．［１ｌ（ｓ、３１１）６．
３０−Ｇ、（ｉｏ（ｓ、２１１）
Ｉ Ｒ２２２０，１７４０，１６９０，１８７０ｃ＋ｌ
！−’元素分（１１（％）；Ｃ１５Ｈ２２０３としての
実測値 Ｃ；７１゜６１．Ｈ，８，７４計算値 Ｃ；７
１．９６．Ｈ，８，８５同様なｈ°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（品師：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２０ｃ１−１ユに稲いもち病罹病藁（Ｐｙｒｉ
ｃｕｌａｒｉａｏｒｙｚａｅ）を設置して、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カップ当り１０茎（２
０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）
０１φ ０％
１ ・・・１０％未満
２ ・・・１０％以上２５％未満
３ ・・・２５％以上５０％未満
４ ・・壷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Ｇ１１ｉ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・ ・防除価 ０〜５０％
その結果を表２に示す。なお、稲に対する薬害は認めら
れなかった。
表２
【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
ルボン酸誘導体は、稲いもち病に対し高いｐ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５′【出願人
東ソー株式会社[Function] As described above, the unsaturated aliphatic carboxylic acid derivative of the present invention is represented by 1:, a symbol [1]. -Crest hole [1]
Among them, R is a carbon number 1 such as methyl group, ethyl group, propyl group, etc.
~3 alkyl group, m1n is selected from an integer from 2 to 12. A preferable example of m is an integer of 5 to 9, and a preferable example of n is an integer of 2 to B. The following can be mentioned as such specific examples. (1) 7-oxotetradec-8-en-10-ynecarboxylic acid methyl ester (2) 7-oxoben-deca-8-dyne-10-ynecarboxylic acid methyl ester (3) 7-oxohexadeca-8- En-10-ynecarboxylic acid methyl ester (4) 7-oxoctadeca-8-en-10-ynecarboxylic acid methyl ester (5) 7-oxooctadec-8-en-10-ynecarboxylic acid methyl ester ( 6) 8-oxobentadec-9-en-11-ynecarboxylic acid methyl ester (7) 8-oxohexadec-9-ene-11-ynecarboxylic acid methyl ester (8) 8-oxoheptadec-9-ene-11 -ynecarboxylic acid methyl ester (9) 8-oxooctadec-9-ene-11-ynecarboxylic acid methyl ester (10) 8-oxononadec-9-ene-11=ynecarboxylic acid methyl ester (11) 9-oxo Hexadec-10-en-12-ynecarboxylic acid methyl ester [2] 9-oxoheptadec-10-en-12-ynecarboxylic acid methyl ester (13) 9-oxooctadec-10-en-12-ynecarboxylic acid Methyl ester (14) 9-oxononadec-10-en-12-ynecarboxylic acid methyl ester (15) 9-oxoeicosa-10-ene-12-ynecarboxylic acid methyl ester (16) 10-oxoheptadec-11-ene-13 −
incarboxylic acid methyl ester (17) 10-oxooctadec-11-ene-13-
Incarboxylic acid methyl ester (1g) 10-oxononadec-11-en-13-ynecarboxylic acid methyl ester (19) 10-oxoeicosa-enien-13-ynecarboxylic acid methyl ester (20) 10-oxoheneicosa-11 -en-13
-ynecarboxylic acid methyl ester (2) 11-oxooctadec-12-ene-14-ynecarboxylic acid methyl ester (22) 11-oxononadec-12-ene-14-ynecarboxylic acid methyl ester (23) 11- Oxoeicosa-12-en-14-ynecarboxylic acid methyl ester (24) 11-oxoheneicosa-12-ene-14
-ynecarboxylic acid methyl ester (25) 11-oxodocos-12-en-14-ynecarboxylic acid methyl ester The unsaturated aliphatic carboxylic acid derivative of the present invention can be produced, for example, according to the following formula. [11 [m] That is, produced by reacting the phosphonate compound represented by -Moonana [■] with the Alda 41 compound represented by the general formula [I [I] in the presence of salt μ in the presence of a solvent or in the absence of a solvent. can. Examples of the solvent include polar solvents such as acetonitrile, glyme, tetrahydrofuran, dioxane, and N,N-dimethylformamide. As a base, 1
．． 8-Diazabicyclo[5゜4.01-7-undecene, 1,8-diazabicyclo[2,2,21 octane, tertiary amines such as triethylamine; sodium hydride,
Examples include metal hydride compounds such as potassium hydride; alkyl metals such as butyllithium; and the like. This reaction can be produced by reacting at θ°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 an effective preventive agent for controlling rice blast disease, particularly rice blast, which occurs in rice fields, and on the other hand, virtually no phytotoxicity to rice was observed. When using the compound of the present invention as a complementary pest control agent,
Although it may be used as it is without adding other ingredients, it is usually mixed with a solid carrier, a liquid, a surfactant, 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%. Solid TT materials include kaolin clay, attabulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob, walnut shell powder, urea, ammonium sulfate, synthetic hydrous silicon oxide, etc. There are fine powders or granules. Liquid carriers include alcohols such as xylene, isopropanol, ethylene glycol, and cellosolve; ketones such as a7tone, cyclohexanone, and isophorone; dimethyl sulfoxide, acetonitrile, water, and the like. Surfactants used for emulsification, dispersion, temperature range, etc. include alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, alkyl sulfate ester salts, and formalin naphthalene sulfonate. Examples include anionic surfactants such as condensates; nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene, and polyoxypropylene block copolymer sorbicun fatty acid ester. Formulation hli aids include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), PA
P (acidic isopropyl phosphate) and the like. What is the compound of the present invention? ; Although it can be used alone, for example, fungicides such as thiuram, dithianon validamidine A5 polyoxin, cerocidin, Marathon, Sumithion, NAC
, BPMC, and other insecticides, herbicides, fertilizer components, etc., to expand the scope of application as a fungicide to agricultural crops, or to exhibit the effects of insecticide, herbicide, or fertilizer 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-oxothene-deca-8-dyne-10-ynecarboxylic acid methyl ester (compound number 1) In a nitrogen stream, dimethyl 2-oxo- 0.62 g of butylphosphonate to 7-medoxycarponyl was added dropwise at room temperature. Then, 1°8-diazabicyclo[5,
A solution of 0.46 g of 4,01-7-undecene in acetonitrile and a solution of 0.50 g of 2-octen-4-ynal in acetonitrile were sequentially added dropwise and stirred for 45 minutes. Add 100 ml of ether to the reaction solution, filter, and remove the ether phase by
After washing with % hydrochloric acid, saturated hydrogenated water, and saturated brine, it was dried over anhydrous magnesium sulfate. The ether was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain the desired product 0.
．． Obtained 52 g (oi 1). 'H-NMR (solvent: CDCI unit: δppm
) 0.70-2.00 (嘗, ILJRI, 2.00-2
．． 70 (m, 011), 3. [1l(s, 311)6.
30-G, (io(s, 211) I R2220, 1740, 1690, 1870c+l
! -' Elemental content (11 (%); Actual value as C15H2203 C; 71°61.H,8,74 Calculated value C; 7
1.96. H,8,85 Representative examples of the compounds of the present invention obtained by the same h° 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 Chemical 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 rice blast disease-affected straw (Pyri
culariaoryzae) was placed and left 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, using the method below to calculate 10 stems (2
0 stems), and the disease severity and control value were determined according to formulas (1) and (2). Disease index Disease area rate Note) 01φ 0% 1 ... Less than 10% 2 ... 10% or more and less than 25% 3 ... 25% or more and less than 50% 4 ... Jar 50% or more Note) To the surveyed leaf area Control value of the area occupied by this lesion - Formula (2) Control G11i is expressed by the symbols A, B, C%D. A... Control value 90-100% B... Control value 70-90% C. - Control value 50-70% D. - Control value 0-50% The results are shown in Table 2. In addition, no chemical damage to rice was observed. Table 2 [Effects of the Invention] As is clear from the above explanation, the long-chain unsaturated carboxylic acid derivative of the present invention exhibits a high p-preventing effect against rice blast, and can be used in agriculture to protect rice from rice blast. It is useful as a disinfectant. Moreover, it is highly safe and can be used extremely safely for rice. Patent 5' [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。 ）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. ) 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 |
|---|---|---|---|
| JP32619788A JPH02172951A (en) | 1988-12-26 | 1988-12-26 | Plant blight controlling agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32619788A JPH02172951A (en) | 1988-12-26 | 1988-12-26 | Plant blight controlling agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02172951A true JPH02172951A (en) | 1990-07-04 |
Family
ID=18185100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32619788A Pending JPH02172951A (en) | 1988-12-26 | 1988-12-26 | Plant blight controlling agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02172951A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6093680A (en) * | 1996-10-25 | 2000-07-25 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
-
1988
- 1988-12-26 JP JP32619788A patent/JPH02172951A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6093680A (en) * | 1996-10-25 | 2000-07-25 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
| US6093681A (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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