JPH02169546A - Controlling agent against plant disease injury - Google Patents
Controlling agent against plant disease injuryInfo
- Publication number
- JPH02169546A JPH02169546A JP32193988A JP32193988A JPH02169546A JP H02169546 A JPH02169546 A JP H02169546A JP 32193988 A JP32193988 A JP 32193988A JP 32193988 A JP32193988 A JP 32193988A JP H02169546 A JPH02169546 A JP H02169546A
- Authority
- JP
- Japan
- Prior art keywords
- methyl ester
- acid methyl
- formula
- controlling agent
- agent against
- 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
- 201000010099 disease Diseases 0.000 title abstract description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract description 7
- 230000006378 damage Effects 0.000 title abstract description 4
- 208000027418 Wounds and injury Diseases 0.000 title 1
- 208000014674 injury Diseases 0.000 title 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000645 desinfectant Substances 0.000 claims 1
- -1 Methyl 11-hydroxytetradec-9-en-7-ynecarboxylate Chemical compound 0.000 abstract description 50
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 15
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 5
- 241000196324 Embryophyta Species 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 241001330975 Magnaporthe oryzae Species 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
- 230000002070 germicidal effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 241000209094 Oryza Species 0.000 description 14
- 235000007164 Oryza sativa Nutrition 0.000 description 14
- 235000009566 rice Nutrition 0.000 description 14
- 150000004702 methyl esters Chemical class 0.000 description 13
- 239000002253 acid Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000000855 fungicidal effect Effects 0.000 description 5
- 239000000417 fungicide Substances 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 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
- 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
- 230000003449 preventive effect Effects 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
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives 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
- 239000004009 herbicide Substances 0.000 description 2
- 239000004615 ingredient 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
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- KQDQZEZWWRPNQH-UHFFFAOYSA-N 1,3-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1CN2 KQDQZEZWWRPNQH-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes 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
- 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
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052570 clay Inorganic materials 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
- 239000006185 dispersion Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 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
- 239000008187 granular material 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
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 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-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
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 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
- 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 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
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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。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 containing the same. More specifically, it relates to a rice blast control agent.
［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。[Prior Art] The bactericidal activity of unsaturated aliphatic carboxylic acid derivatives has been known for a long time, and for example, octadecatriene carboxylic acid oxides are disclosed in JP-A-59-148706.
［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。[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.
Ｅ問題点を解決するための手段］
本発明の１」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供するこ
とにある。[Means for Solving Problem E] The first object of the present invention is 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 using the same as an active ingredient. The aim is to provide agents for
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。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.
すなわち、本発明は
−数式［１］
（ただし、Ｒは炭素数１〜３のアルキル基を表わし、ｍ
は５から９の整数を示し、ｎは２から６の整数を示す。That is, the present invention is based on the formula [1] (wherein R represents an alkyl group having 1 to 3 carbon atoms, and m
represents an integer from 5 to 9, and n represents an integer from 2 to 6.
）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［１］で表わされる不飽和脂肪族カルボン酸誘導
体を倚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。) and an unsaturated aliphatic carboxylic acid derivative represented by general formula [1] as masticatory ingredients.
［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、」二足一般式［Ｉ］で示される。[Function] As described above, the unsaturated aliphatic carboxylic acid derivative of the present invention is represented by the bipedal general formula [I].
数式［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。In formula [1], R represents an alkyl group having 1 to 3 carbon atoms such as a methyl group, ethyl group, or propyl group, and 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.
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。The following can be mentioned as such specific examples.
（１）１１−オキソテトラゾカー９−エン−７−インカ
ルボン酸メチルエステル
（２）１１−オキソベンタデカー９−エン−７＝インカ
ルボン酸メチルエステル
（３）１１−オキソヘキサデカ−９−エン−７−インカ
ルボン酸メチルエステル
（４）１１−オキソヘプタデカ−９−エン−７−インカ
ルボン酸メチルエステル
（５）１１−オキソオクタデカ−９−エン−７−インカ
ルボン酸メチルエステル
（６）１２−オキソベンタデカー１０−エン−８−イン
カルボン酸メチルエステル
（７）１２−オキソヘキサデカ−１０−エン−８−イン
カルボン酸メチルエステル
（８）１２−オキソヘプタデカ−１０−エン−８−イン
カルボン酸メチルエステル
（９）１２−オキソオクタデカ−１０−エン−８−イン
カルボン酸メチルエステル
（１０）１２−オキソノナデカ−１０−エン−８−イン
カルボン酸メチルエステル
（１１）１３−オキソヘキサデカ−１１−エン−９−イ
ンカルボン酸メチルエステル
（１２）１３−オキソヘプタデカ−１１−エン−９−イ
ンカルボン酸メチルエステル
（１３）１３−オキソオクタデカ−１１−エン−９−イ
ンカルボン酸メチルエステル
（１４）１３−オキソノナデカ−１１−エン−９−イン
カルボン酸メチルエステル
（１５）１３−オキソエイコサ−１１−エン−９−イン
カルボン酸メチルエステル
（１Ｂ）１４−オキソヘプタデカ−１２−エン−１０−
インカルボン酸メチルエステル
（１７）１４−オキソオクタデカ−１２−エン−１０−
インカルボン酸メチルエステル
（１ｇ）１４−オキソノナデカ−１２−エン−１０−イ
ンカルボン酸メチルエステル
（１９）１４−オキソエイコサ−１２−エン−１０−イ
ンカルボン酸メチルエステル
（２０）１４−オキソヘンエイコサ−１２−エン−１０
−インカルボン酸メチルエステル（２１）１５−オキソ
オクタデカ−１３−エン−１１−インカルボン酸メチル
エステル
（２２）１５−オキソノナデカ−１３−エン−１１−イ
ンカルボン酸メチルエステル
（２３）１５−オキソエイコサ−１３−エン−１１−イ
ンカルボン酸メチルエステル
（２４）１５−オキソヘンエイコサ−１３−エン−１１
−インカルボン酸メチルエステル（２５）１５−オキソ
ドコサ−１３−エン−１１−イ〉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。(1) 11-oxotetrazocar9-en-7-ynecarboxylic acid methyl ester (2) 11-oxobentadecar9-ene-7=ynecarboxylic acid methyl ester (3) 11-oxohexadeca-9- En-7-ynecarboxylic acid methyl ester (4) 11-oxoheptadec-9-en-7-ynecarboxylic acid methyl ester (5) 11-oxooctadec-9-en-7-ynecarboxylic acid methyl ester (6) 12-Oxobentadec-10-en-8-ynecarboxylic acid methyl ester (7) 12-oxohexadec-10-en-8-ynecarboxylic acid methyl ester (8) 12-oxoheptadec-10-en-8-yne Carboxylic acid methyl ester (9) 12-oxooctadec-10-en-8-ynecarboxylic acid methyl ester (10) 12-oxononadec-10-en-8-ynecarboxylic acid methyl ester (11) 13-oxohexadeca -11-en-9-ynecarboxylic acid methyl ester (12) 13-oxoheptadec-11-en-9-ynecarboxylic acid methyl ester (13) 13-oxooctadec-11-en-9-ynecarboxylic acid methyl ester (14) 13-oxononadec-11-en-9-ynecarboxylic acid methyl ester (15) 13-oxoeicosa-11-en-9-ynecarboxylic acid methyl ester (1B) 14-oxoheptadec-12-ene-10-
incarboxylic acid methyl ester (17) 14-oxooctadec-12-ene-10-
Incarboxylic acid methyl ester (1g) 14-oxononadec-12-en-10-ynecarboxylic acid methyl ester (19) 14-oxoeicosa-12-en-10-ynecarboxylic acid methyl ester (20) 14-oxoheneicosa -12-en-10
-ynecarboxylic acid methyl ester (21) 15-oxooctadec-13-en-11-ynecarboxylic acid methyl ester (22) 15-oxononadec-13-en-11-ynecarboxylic acid methyl ester (23) 15-oxoeicosa -13-en-11-ynecarboxylic acid methyl ester (24) 15-oxoheneicosa-13-ene-11
-ynecarboxylic acid methyl ester (25) 15-oxodocos-13-en-11-y>carboxylic acid methyl ester The unsaturated aliphatic carboxylic acid derivative of the present invention can be produced, for example, according to the following formula.
［ｎ］
［ＩＩＩ］
すなわち、−数式［１１］で表わされるホスホネ−＋一
体と一般式［Ｉ［１］で表わされるアルデヒド体を溶媒
存（ｌミかあるいは無溶媒中、塩基存在下反応させるこ
とにより製造できる。[n] [III] That is, the phosphonate represented by the formula [11] and the aldehyde represented by the general formula [I [1] are reacted in the presence of a base in the presence of a solvent or in the absence of a solvent. It can be manufactured by
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゜４．０］−７−ウンデセン
、１，８−ジアザビシクロ［２，２，２］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。Examples of the solvent include polar solvents such as acetonitrile, glyme, tetrahydrofuran, dioxane, and N,N-dimethylformamide. As a base, 1
．． Tertiary amines such as 8-diazabicyclo[5°4.0]-7-undecene, 1,8-diazabicyclo[2,2,2]octane, triethylamine; sodium hydride,
Examples include metal hydride compounds such as potassium hydride; alkyl metals such as butyllithium; and the like.
この反応は、Ｏ℃〜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。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.
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。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.
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ｈｌｉ助剤と混合
して、乳剤、水和剤、懸濁剤、粒剤等に製剤する。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 aids to formulate emulsions, wettable powders, suspensions, granules, 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１〜９９％含何す
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 1 to 99%.
固体１１１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。The 111 solids include fine powders such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Or there are particles.
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。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.
乳化、分散、湿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′：
ｑ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） 、ＰＡ
Ｐ （酸性燐酸イソプロピル）等が挙げられる。Surfactants used for emulsification, dispersion, wetting, etc. include alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, alkyl sulfate ester salts, and formalin naphthalene sulfonate. Anionic surfactants such as condensates; nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene, and polyoxypropylene block copolymer sorbicun fatty acid esters:
An example is q. Formulation aids include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), PA
P (acidic isopropyl phosphate) and the like.
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。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.
［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。[Examples] Hereinafter, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited to these.
実施例１
１１−オキソテトラゾカー９−二ンー７−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−オキソペンチル
ホスホナート０．６２ｇを室温下滴下した。その後、１
．８−ジアザビシクロ［５゜４、Ｏ］−７−ウンっ゛上
２０．４６ｇのアセトニトリル溶液、９−ホル、ルノニ
ルー７−インカルボン酸メチルエステル０．５０ｇのア
セトニトリル溶液を順次滴下し、４５分間；り咋した。Example 1 Preparation of 11-oxotetrazocar 9-dyn-7-ynecarboxylic acid methyl ester (Compound No. 1) In a nitrogen stream, dimethyl 2-oxopentyl was added to a suspension of 0.14 g of anhydrous lithium chloride in 30 ml of acetonitrile. 0.62 g of phosphonate was added dropwise at room temperature. After that, 1
．． 20.46 g of acetonitrile solution and 0.50 g of 9-hol, lunonyl-7-ynecarboxylic acid methyl ester solution were added dropwise onto 8-diazabicyclo[5°4,O]-7-un for 45 minutes; I spoke.
反応液にエーテル１００ｍ１を加えて濾過ニア、エーテ
ル相を３９６塩酸、飽和重曹水、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
、ＬＩ的物０．５２ｇ （ｏｆ ］）を１１１だ。100 ml of ether was added to the reaction solution and filtered. The ether phase was washed with 396 hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine, and then dried over anhydrous magnesium sulfate. The ether was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 0.52 g (of ) of LI-like product.
’Ｈ−ＮＭＲ（溶媒： ＣＤＣＩ 単位：δｐｐｍ
）０．９０（ｔ、３１１．Ｊ＝７１１ｚ）、１．２５
−２．００（ｍ、８１１）、２．１０−２．［ｉ５（ｗ
＋、６１１）、３．８５（ｓ、ａｌｌ）、０．５３（ｄ
、２１１．Ｊ−［１１１ｚ）ＩＲ１７４０，１６８０ｃ
ｍ−１
元素分析（％）：Ｃ１５Ｈ２２０３としての実１ｌｌ（
ｉｉ Ｃ； ７１． ６１． Ｈ； ８． ７４計算
値 Ｃ；７１．９６．Ｈ；ｄ、８５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。'H-NMR (solvent: CDCI unit: δppm
) 0.90 (t, 311.J=711z), 1.25
-2.00 (m, 811), 2.10-2. [i5(w
+, 611), 3.85 (s, all), 0.53 (d
, 211. J-[111z)IR1740,1680c
m-1 Elemental analysis (%): 1 ll of fruit as C15H2203 (
ii C; 71. 61. H; 8. 74 Calculated value C; 71.96. H; d, 85 Representative examples of the compounds of the present invention obtained by a similar method and their physical properties are shown in Table 1.
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、
主剤含を量５％の乳剤を得た。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.
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上に稲いもち病罹病′１Ｓ（Ｐｙｒｉ
ｃｕｌａｒｉａｏｒｙｚａｅ）を設置して、４０間静置
した。Example 3 Preventive effect test against rice blast
Example 2: 3 cups of rice (variety: Koshihikari) grown in 1) at the 4, 0-4.5 leaf stage were placed on a turntable.
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 a rice blast disease infected '1S (Pyri
culariaoryzae) and allowed to stand for 40 minutes.
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゛（
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。For each cup, calculate the proportion of main lesions on the 3rd and 4th true leaves to each leaf area by measuring 10 stems per cup (
20 stems), and the disease severity and control value were determined according to formulas (1) and (2).
発病指数 発病面積率 注） ０ −０％ １ ・１０％未満 ２ １０％以上２５％未満 ３ ・２５％以上５０％未満 ４ ・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、ＣＳＤの記号で表した。Disease index, disease area rate, note) 0 -0% 1 ・Less than 10% 2 10% or more but less than 25% 3. ・25% or more but less than 50% 4 ・50% or more Note) Main lesion area in surveyed leaf area Control value - Formula (2) The control value was expressed by the symbols A, B, and CSD.
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。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.
［発明の効果コ
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予防効果を示
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。[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 preventive effect against rice blast, and can be used as an agricultural fungicide for protecting rice against rice blast. It is useful. Moreover, it is highly safe and can be used extremely safely for rice.
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 |
|---|---|---|---|
| JP32193988A JPH02169546A (en) | 1988-12-22 | 1988-12-22 | Controlling agent against plant disease injury |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32193988A JPH02169546A (en) | 1988-12-22 | 1988-12-22 | Controlling agent against plant disease injury |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02169546A true JPH02169546A (en) | 1990-06-29 |
Family
ID=18138107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32193988A Pending JPH02169546A (en) | 1988-12-22 | 1988-12-22 | Controlling agent against plant disease injury |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02169546A (en) |
Cited By (2)
| 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 |
| CN109627162A (en) * | 2017-10-06 | 2019-04-16 | 信越化学工业株式会社 | The method for preparing (7E) -7,9- decadinene acid esters |
-
1988
- 1988-12-22 JP JP32193988A patent/JPH02169546A/en active Pending
Cited By (8)
| 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 |
| CN109627162A (en) * | 2017-10-06 | 2019-04-16 | 信越化学工业株式会社 | The method for preparing (7E) -7,9- decadinene acid esters |
| JP2019069907A (en) * | 2017-10-06 | 2019-05-09 | 信越化学工業株式会社 | Process for producing (7e)-7,9-decadienoic acid ester |
| CN109627162B (en) * | 2017-10-06 | 2022-11-15 | 信越化学工业株式会社 | Process for preparing (7E) -7, 9-decanedioic acid esters |
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