JPWO2018168860A1 - 植物賦活剤 - Google Patents
植物賦活剤 Download PDFInfo
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- JPWO2018168860A1 JPWO2018168860A1 JP2019506048A JP2019506048A JPWO2018168860A1 JP WO2018168860 A1 JPWO2018168860 A1 JP WO2018168860A1 JP 2019506048 A JP2019506048 A JP 2019506048A JP 2019506048 A JP2019506048 A JP 2019506048A JP WO2018168860 A1 JPWO2018168860 A1 JP WO2018168860A1
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- plant activator
- fatty acid
- plant
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- 239000005962 plant activator Substances 0.000 title claims abstract description 68
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 62
- 229930195729 fatty acid Natural products 0.000 claims abstract description 62
- 239000000194 fatty acid Substances 0.000 claims abstract description 62
- -1 oxo fatty acid Chemical class 0.000 claims abstract description 51
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 239000004480 active ingredient Substances 0.000 claims abstract description 8
- JHXAZBBVQSRKJR-UHFFFAOYSA-N coriolic acid Natural products CCCCCC(=O)C=CC=CCCCCCCCC(O)=O JHXAZBBVQSRKJR-UHFFFAOYSA-N 0.000 claims description 24
- PMTMAFAPLCGXGK-JMTMCXQRSA-N (15Z)-12-oxophyto-10,15-dienoic acid Chemical compound CC\C=C/C[C@H]1[C@@H](CCCCCCCC(O)=O)C=CC1=O PMTMAFAPLCGXGK-JMTMCXQRSA-N 0.000 claims description 17
- PMTMAFAPLCGXGK-UHFFFAOYSA-N OPDA Natural products CCC=CCC1C(CCCCCCCC(O)=O)C=CC1=O PMTMAFAPLCGXGK-UHFFFAOYSA-N 0.000 claims description 15
- JHXAZBBVQSRKJR-BSZOFBHHSA-N 13-oxo-9Z,11E-ODE Chemical group CCCCCC(=O)\C=C\C=C/CCCCCCCC(O)=O JHXAZBBVQSRKJR-BSZOFBHHSA-N 0.000 claims description 8
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- ZNJFBWYDHIGLCU-HWKXXFMVSA-N jasmonic acid Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-HWKXXFMVSA-N 0.000 description 12
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- RIGGEAZDTKMXSI-JPAZTHTMSA-N (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid Chemical compound CC\C=C\C\C=C\C=C\C(O)CCCCCCCC(O)=O RIGGEAZDTKMXSI-JPAZTHTMSA-N 0.000 description 2
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- YUPHIKSLGBATJK-OBKPXJAFSA-N 9-HOTE Chemical compound CC\C=C/CC\C=C\C=C(\O)CCCCCCCC(O)=O YUPHIKSLGBATJK-OBKPXJAFSA-N 0.000 description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 2
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
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- 102000023984 PPAR alpha Human genes 0.000 description 2
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- 229930195482 Validamycin Natural products 0.000 description 2
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- 230000000844 anti-bacterial effect Effects 0.000 description 2
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- 230000000052 comparative effect Effects 0.000 description 2
- 239000002299 complementary DNA Substances 0.000 description 2
- NHSCRWJPZDNMBU-UHFFFAOYSA-L dipotassium carbonic acid carbonate Chemical compound [K+].[K+].OC([O-])=O.OC([O-])=O NHSCRWJPZDNMBU-UHFFFAOYSA-L 0.000 description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
- 230000005059 dormancy Effects 0.000 description 2
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- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- FELONIKRCJBDIO-ZAJAATJQSA-N (2e,4e,6e)-deca-2,4,6-trienoic acid Chemical compound CCC\C=C\C=C\C=C\C(O)=O FELONIKRCJBDIO-ZAJAATJQSA-N 0.000 description 1
- ZUUFLXSNVWQOJW-MBIXAETLSA-N (2e,4e,6e)-octadeca-2,4,6-trienoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C(O)=O ZUUFLXSNVWQOJW-MBIXAETLSA-N 0.000 description 1
- BWLORZJWVOWJRJ-UHFFFAOYSA-N 16-(oxiren-2-yl)hexadec-15-enoic acid Chemical compound C1=C(C=CCCCCCCCCCCCCCC(=O)O)O1 BWLORZJWVOWJRJ-UHFFFAOYSA-N 0.000 description 1
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- JRIHOQHSQJDCKE-UHFFFAOYSA-N 2-hydroperoxyoctadeca-2,4,6-trienoic acid Chemical compound CCCCCCCCCCCC=CC=CC=C(OO)C(O)=O JRIHOQHSQJDCKE-UHFFFAOYSA-N 0.000 description 1
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- 239000012190 activator Substances 0.000 description 1
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- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
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Images
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P15/00—Biocides for specific purposes not provided for in groups A01P1/00 - A01P13/00
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P21/00—Plant growth regulators
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Botany (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cultivation Of Plants (AREA)
Abstract
Description
HOOC−(R1)−C=C−C(=O)−R2 (I)
(式中、
R1:直鎖または分岐の、炭素数6〜12のアルキル基であって、1つまたはそれ以上の二重結合を含んでいてもよく、
R2:炭素数2〜8のアルキル基であって、1つまたはそれ以上の分岐および/または二重結合を含んでいてもよい)
の構造式を有するオキソ脂肪酸誘導体またはその塩もしくはエステルを有効成分として含むことを特徴とする植物賦活剤に関する。
本発明の植物賦活剤は、オキソ脂肪酸誘導体であって、以下の式:
HOOC−(R1)−C=C−C(=O)−R2 (I)
(式中、
R1:直鎖または分岐の、炭素数6〜12のアルキル基であって、1つまたはそれ以上の二重結合を含んでいてもよく、
R2:炭素数2〜8のアルキル基であって、1つまたはそれ以上の分岐および/または二重結合を含んでいてもよい)
の構造式を有するオキソ脂肪酸誘導体、またはその塩もしくはエステルを有効成分として含むことを特徴とする。本発明はまた、すべての幾何異性体および立体異性体を含む式(I)の化合物またはその塩もしくはエステルを有効成分として含む植物賦活剤に関する。
実施例1として、0.012%の13−オキソ−9,11−オクタデカジエン酸を含む0.15%炭酸水素二カリウム水溶液を調製した。なお、13−オキソ−9,11−オクタデカジエン酸としては、(9Z,11E)−13−オキソ−9,11−オクタデカジエン酸(13−oxoODA、ケイマンケミカル社製)を用いた。比較例として、0.012%の脂肪酸類縁物質である13−HPODE((9Z,11E)−13−ヒドロペルオキシ−9,11−オクタデカジエン酸、ケイマンケミカル社製)、9−HPODE((10Z,12E)−9−ヒドロペルオキシ−10,12−オクタデカジエン酸、ケイマンケミカル社製)、9−HPOTE((10E,12Z,15Z)−9−ヒドロペルオキシ−10,12,15−オクタデカトリエン酸、ケイマンケミカル社製)、9−HOTE((10E,12Z,15Z)−9−ヒドロキシ−10,12,15−オクタデカトリエン酸、ケイマンケミカル社製)、13−HPOTE((9Z,11E,15Z)−13−ヒドロペルオキシ−9,11,15−オクタデカトリエン酸、ケイマンケミカル社製)、13−HOTE((9Z,11E,15Z)−13−ヒドロキシ−9,11,15−オクタデカトリエン酸、ケイマンケミカル社製)および12−OPDA(12−オキソ−フィトジエン酸、ケイマンケミカル社製)、ならびに、0.012%のα−ケトール脂肪酸をそれぞれ含む0.15%炭酸水素二カリウム水溶液をそれぞれ調製した。なお、α−ケトール脂肪酸水溶液は、次のような合成手段で合成した。
実施例2として、0.012%の13−オキソ−9,11−オクタデカジエン酸を含む0.15%リン酸水素二カリウム水溶液を調製した。なお、13−オキソ−9,11−オクタデカジエン酸としては、(9Z,11E)−13−オキソ−9,11−オクタデカジエン酸(13−oxoODA、ケイマンケミカル社製)を用いた。比較例として、0.012%の脂肪酸類縁物質である13−HPODE((9Z,11E)−13−ヒドロペルオキシ−9,11−オクタデカジエン酸、ケイマンケミカル社製)、9−HPODE((10Z,12E)−9−ヒドロペルオキシ−10,12−オクタデカジエン酸、ケイマンケミカル社製)、9−HPOTE((10E,12Z,15Z)−9−ヒドロペルオキシ−10,12,15−オクタデカトリエン酸、ケイマンケミカル社製)、9−HOTE((10E,12Z,15Z)−9−ヒドロキシ−10,12,15−オクタデカトリエン酸、ケイマンケミカル社製)、13−HPOTE((9Z,11E,15Z)−13−ヒドロペルオキシ−9,11,15−オクタデカトリエン酸、ケイマンケミカル社製)、13−HOTE((9Z,11E,15Z)−13−ヒドロキシ−9,11,15−オクタデカトリエン酸、ケイマンケミカル社製)および12−OPDA(12−オキソ−フィトジエン酸、ケイマンケミカル社製)、ならびに、0.012%のα−ケトール脂肪酸をそれぞれ含む0.15%リン酸水素二カリウム水溶液をそれぞれ調製した。なお、α−ケトール脂肪酸水溶液は、実施例1と同様の合成手段で合成した。
(9Z,11E)−13−オキソ−9,11−オクタデカジエン酸(13−oxoODA、ケイマンケミカル社製)と脂肪酸類縁物質である12−OPDA(12−オキソ−フィトジエン酸、ケイマンケミカル社製)とをそれぞれ0.012%含む、0.15%炭酸水素二カリウム水溶液を調製した。
(9Z,11E)−13−オキソ−9,11−オクタデカジエン酸(13−oxoODA、ケイマンケミカル社製)と脂肪酸類縁物質である12−OPDA(12−オキソ−フィトジエン酸、ケイマンケミカル社製)とをそれぞれ0.012%含む、0.15%リン酸水素二カリウム水溶液を調製した。
Claims (12)
- 以下の式:
HOOC−(R1)−C=C−C(=O)−R2 (I)
(式中、
R1:直鎖または分岐の、炭素数6〜12のアルキル基であって、1つまたはそれ以上の二重結合を含んでいてもよく、
R2:炭素数2〜8のアルキル基であって、1つまたはそれ以上の分岐および/または二重結合を含んでいてもよい)
の構造式を有するオキソ脂肪酸誘導体またはその塩もしくはエステルを有効成分として含むことを特徴とする植物賦活剤。 - 請求項1記載の植物賦活剤であって、前記オキソ脂肪酸誘導体の、
R1のアルキル基の炭素数が8〜10であり、
R2のアルキル基の炭素数が4〜6である。 - 請求項1または2記載の植物賦活剤であって、前記オキソ脂肪酸誘導体の、
R1が、式(I)におけるカルボニル基のαおよびβ炭素の間の二重結合と共役二重結合を形成する二重結合を含む。 - 請求項3記載の植物賦活剤であって、前記オキソ脂肪酸誘導体の、
R1が、炭素数9のアルキル基であり、
R2が、炭素数5のアルキル基である。 - 請求項4記載の植物賦活剤であって、前記オキソ脂肪酸誘導体が、(9Z、11E)−13−オキソ−9,11−オクタデカジエン酸またはその塩である。
- 請求項5記載の植物賦活剤であって、前記オキソ脂肪酸誘導体が、(9Z、11E)−13−オキソ−9,11−オクタデカジエン酸である。
- 12−オキソ−フィトジエン酸またはその塩をさらに含む請求項1〜6のいずれか1項に記載の植物賦活剤。
- 界面活性剤および/または希釈剤もしくは担体をさらに含む請求項1〜7のいずれか1項に記載の植物賦活剤。
- 前記オキソ脂肪酸誘導体またはその塩もしくはエステルの濃度が、0.012〜0.12g/lである請求項1〜8のいずれか1項に記載の植物賦活剤。
- 前記12−オキソ−フィトジエン酸またはその塩の濃度が、0.012〜0.12g/lである請求項7記載の植物賦活剤。
- 植物の茎葉もしくは根に接触させる噴霧剤もしくは浸漬用薬剤、または、土壌灌注用薬剤として用いられる請求項1〜10のいずれか1項に記載の植物賦活剤。
- 前記植物賦活剤は、アブラナ科植物に対して使用される請求項1〜11のいずれか1項に記載の植物賦活剤。
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