JPS623801B2 - - Google Patents
Info
- Publication number
- JPS623801B2 JPS623801B2 JP4386579A JP4386579A JPS623801B2 JP S623801 B2 JPS623801 B2 JP S623801B2 JP 4386579 A JP4386579 A JP 4386579A JP 4386579 A JP4386579 A JP 4386579A JP S623801 B2 JPS623801 B2 JP S623801B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- compound
- alkyl group
- substituted
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 230000005097 photorespiration Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- -1 isopentenyl group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- DCEMCPAKSGRHCN-UHFFFAOYSA-N oxirane-2,3-dicarboxylic acid Chemical compound OC(=O)C1OC1C(O)=O DCEMCPAKSGRHCN-UHFFFAOYSA-N 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 230000029553 photosynthesis Effects 0.000 description 3
- 238000010672 photosynthesis Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241001464837 Viridiplantae Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 150000001722 carbon compounds Chemical class 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 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
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 230000000243 photosynthetic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は光呼吸阻害剤に関するものである。
農業生産を生物学的に見た場合に、その特徴は
緑色植物の光合成能力を利用して、地球上に太陽
エネルギーを蓄積する方法で生産を行なう点にあ
り、併せて大気中に酸素を供給していることにな
る。しかしこれは太陽エネルギーの利用方法とし
ては必ずしも効率がよいものではない。世界の食
糧事情をみた場合、今世紀末には世界の人口が現
在のほゞ倍位になるものと予想されており、この
人口増大に対処するための食糧の確保は極めて困
難であろうと予想されている。
この様な人口増加に対処するために従来多くの
研究努力が払われて来た。しかし農業生産力増強
のために実施されて来た従来の開発研究はその多
くが生産技術の改良に止まり、植物が本来的に具
備している機能の細部を具体的に把握し、それを
強化するという方向への努力がほとんど払われて
いなかつた。一般に植物は光合成作用によつて、
太陽エネルギーを利用して、水と炭酸ガスから炭
水化物を合成し、大気中に酸素を供給している。
一方植物は空気中の酸素を吸収して炭酸ガスを放
出するいわゆる呼吸作用を行なつているが、この
呼収作用には光の照射下で行なわれる光呼吸と暗
所において行なわれる暗呼吸とがあり、光呼吸は
C3植物のみに認められることが知られている。
しかも光呼吸によつて消費される炭素化合物の量
は多く、或る種の植物では光合成によつて、同化
された炭素化合物の50％が光呼吸によつて分離さ
れてしまうといわれている。したがつて植物体内
における他の代謝過程に悪影響を及ぼすことな
く、光呼吸だけを選択的に抑制することが出来れ
ば、それに対応して作物の生産性を高めうる可能
性が期待される。
発明者等は緑色植物による太陽エネルギー固定
機能の増進について研究を行なつた結果、光呼吸
を行なう植物の光呼吸をある種の阻害剤によつて
抑制することによつて、植物の光合成をより効率
的に行なうことが出来ることを発見し、本発明を
完成するに至つた。
本発明剤を利用した場合には例えばイネ、ム
ギ、マメ、サトウダイコンなどの様なC3植物、
即ち食糧の主要な供給源となる植物の光呼吸を抑
制することが可能である。
即ち本発明は、一般式
（たゞしR1、R2はＨ、アルカリもしくはアルカリ
土金属、炭素数１〜12の直鎖状アルキル基、炭素
数３〜４の分枝状アルキル基、アリル基、イソペ
ンテニル基、炭素数３又は６の環状アルキル基、
フエニル基、ハロゲン置換フエニル基、ベンジル
基、ハロゲン置換ベンジル基、チエニル基置換メ
チル基、フリル基置換メチル基を示す）；
（たゞしR3はＨ、炭素数１〜12の直鎖状アルキル
基、炭素数６の環状アルキル基、ハロゲン置換フ
エニル基、ベンジル基、R4はアルカリ金属を示
す）；
又は
（たゞしR5、R6はＨ、炭素数１〜12の直鎖状アル
キル基、アリル基、フエニル基、ベンジル基を示
す）
で示される化合物から選ばれる１種又は２種以上
の化合物を有効成分として含有することを特徴と
する光呼吸阻害剤である。
本発明におけるエポキシコハク酸またはその誘
導体（以下これらを単にエポキシコハク酸類と記
す）はシス型またはトランス型のいずれの化合物
も使用が可能である。
次にエポキシコハク酸類を第１表に例示する。
なお第１表において※はアーニトロベンジルチオ
ウロニウム塩を示す。
The present invention relates to photorespiration inhibitors. From a biological perspective, agricultural production is characterized by the fact that it uses the photosynthetic ability of green plants to accumulate solar energy on the earth, while also supplying oxygen to the atmosphere. That means you are doing it. However, this is not necessarily an efficient way to utilize solar energy. Looking at the world's food situation, it is predicted that by the end of this century the world's population will be approximately double its current level, and it will be extremely difficult to secure enough food to cope with this population increase. ing. Many research efforts have been made to cope with such population growth. However, most of the conventional development research that has been carried out to increase agricultural productivity has stopped at improving production technology, and has focused on concretely grasping the details of the functions that plants inherently have and strengthening them. Little effort has been made in this direction. In general, plants use photosynthesis to
They use solar energy to synthesize carbohydrates from water and carbon dioxide, supplying oxygen to the atmosphere.
On the other hand, plants absorb oxygen from the air and release carbon dioxide gas, which is called respiration. There is, and photorespiration is
It is known to be found only in C3 plants.
Moreover, the amount of carbon compounds consumed through photorespiration is large, and it is said that in some plants, 50% of the carbon compounds assimilated through photosynthesis are separated through photorespiration. Therefore, if photorespiration can be selectively suppressed without adversely affecting other metabolic processes within the plant, it is expected that crop productivity may be increased accordingly. The inventors conducted research on enhancing the solar energy fixation function of green plants, and found that by suppressing the photorespiration of plants with a certain type of inhibitor, they were able to increase the photosynthesis of plants. They have discovered that this can be done efficiently and have completed the present invention. When the agent of the present invention is used, C3 plants such as rice, wheat, beans, sugar beet, etc.
In other words, it is possible to suppress the photorespiration of plants, which are the main source of food. That is, the present invention is based on the general formula (R 1 and R 2 are H, alkali or alkaline earth metal, linear alkyl group having 1 to 12 carbon atoms, branched alkyl group having 3 to 4 carbon atoms, allyl group, isopentenyl group, carbon cyclic alkyl group of number 3 or 6,
phenyl group, halogen-substituted phenyl group, benzyl group, halogen-substituted benzyl group, thienyl-substituted methyl group, furyl-substituted methyl group); (R 3 is H, a linear alkyl group having 1 to 12 carbon atoms, a cyclic alkyl group having 6 carbon atoms, a halogen-substituted phenyl group, a benzyl group, and R 4 is an alkali metal); or (R 5 and R 6 each represent H, a linear alkyl group having 1 to 12 carbon atoms, an allyl group, a phenyl group, or a benzyl group) One or more compounds selected from the following: It is a photorespiration inhibitor characterized by containing as an active ingredient. As the epoxysuccinic acid or its derivatives (hereinafter simply referred to as epoxysuccinic acids) in the present invention, either cis-type or trans-type compounds can be used. Next, Table 1 shows examples of epoxysuccinic acids.
In Table 1, * indicates an arnitrobenzylthiouronium salt.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
本発明に係る化合物は例えば次の様にして製造
することが出来る。
製造例 １
化合物番号２の製造方法
19.7ｇのフマル酸を60mlの水に懸濁し15mlの水
に溶解した10ｇの水酸化ナトリウムを撹拌しなが
ら加えた。
次に9.3ｇのタングステン酸ナトリウムと20ml
の30％過酸化水素水を添加した。はじめ冷却し、
次に加温しながら１時間半63〜64℃に保つた。PH
を４以上に保つために、0.5Nの水酸化ナトリウ
ム水溶液を滴下した。反応終了後、大部分の水を
減圧留去し、残渣を大量のアセトンに注ぎ、ねば
りのある油状の化合物を得た。アセトンを除き更
に新しいアセトンを加えた。この操作を２回繰返
して化合物番号２の結晶を得た。
製造例 ２
化合物番号３の製造方法
製造例１と同じ方法で得られた化合物番号２の
化合物22.5ｇを最少量の水に溶解し、これを、40
ｇの塩化バリウムを溶解した120mlの熱水溶液中
かきまぜながら加えた結果、定量的に化合物番号
３の化合物が得られた。
製造例 ３
化合物番号６の製造方法
25.5ｇの化合物番号３の化合物を90mlの乾燥メ
タノールに溶解した。これを10〜15℃に冷却し、
6.8mlの濃硫酸をかきまぜながら、４時間かけて
滴下した。12時間後、3.6ｇの無水硫酸マグネシ
ウムを加え、混合物をかきまぜながら５時間還流
した。2.8ｇの炭酸カルシウムを加えて、メタノ
ール溶液を加温ロートで過し、溶媒を減圧留去
して、12.3ｇの化合物番号６の化合物を得た。
製造例 ４
化合物番号55の製造方法
0.8ｇの化合物番号６の化合物を開放したビー
カー中で20mlのメタノールに溶かし、激しくかき
まぜながらｎ−オクチルアミン2.6ｇを添加し
た。はじめ冷却し、反応混合物が白濁してきたら
室温に更に１時間かきまぜ、溶媒を留去後、メタ
ノールから再結晶することによつて、化合物番号
55の化合物を得た。
製造例 ５
化合物番号５の化合物の製造方法
11.6ｇの化合物番号６の化合物をメタノール50
mlに溶解し、これに4.6ｇの水酸化カリウムを含
むメタノール溶液120mlを加え、氷冷し、かきま
ぜながら２時間同じ温度に保ち、次に溶媒を留去
し、メタノールにより洗浄して11.2ｇの化合物番
号５の化合物を得た。
製造例 ６
化合物番号28の化合物の製造方法
エポキシコハク酸1.32ｇ、ｎ−オクチルアルコ
ール6.5ｇおよび硫酸30mlからなる混合物をDean
−Stark水分離器に入れ、ベンゼンを溶媒として
還流させた。反応終了後、反応液を重曹水で洗
い、水洗し、乾燥後溶媒を留去した。オクチルア
ルコールを減圧蒸留で除き、シリカゲルカラムク
ロマトグラフイー（ヘキサン−ベンゼン）でベン
ゼン100％の流出区分より化合物番号28の化合物
を得た。
製造例 ７
化合物番号50の化合物の製造方法
開放したビーカー中で、強力なスターラーを用
いて、0.8ｇのコハク酸ジメチルと２mlの冷アン
モニア水とを15分間撹拌を行なつた。生成物を
過により分離し、少量の水で洗浄した。化合物番
号50の化合物の粗結晶0.6ｇが得られた。これを
水から再結して0.52ｇの精製物を得た。
本発明剤を製剤するには例えば粉末、水溶液、
乳濁液、水性または油性懸濁液の様な通常の公知
の任意の剤型に製剤が可能である。
本発明剤の使用量は作物の種類、作物の生育ス
テージ、使用方法または使用時期等によつて異な
るが、一般的には土壌施用の場合には乾土に対し
て化合物即ち有効成分として0.1〜1000ppmであ
り、作物の茎葉部に水溶液で散布する場合には有
効成分として１〜20000ppm好ましくは100〜
10000ppmの濃度の水溶液を散布する。
また本発明剤の使用方法は一般的には水溶液に
して使用するが、肥料と一緒にして土壌中に混和
してもよく、また追肥の際に土壌表面に散布して
もよい。更に液肥、殺虫剤、殺菌剤または葉面散
布剤等と混用することも可能である。なお薬剤が
作物に付着して浸透し易いようにするために、界
面活性剤を添加した水溶液を散布することは好ま
しいことである。本発明剤の使用時期は一般的に
は植物の光呼吸が盛んな時期が好ましく、例えば
植物の生殖生長期から収穫期までの間に使用する
のが好ましい。しかし作物によつては栄養生長期
に使用した場合に、より好ましい効果を示す場合
があるので使用時期は特に限定されるものではな
い。
次に本発明剤の効果を試験例により説明する。
試験例 １
本発明剤に係る化合物を所定の濃度に調整した
ホーグランド水耕液を、紙を敷いたガラスチユ
ーブ（φ2.3cm×15.8cm）に入れ、発芽直後のイ
ネ（品種・日本晴）を10粒宛播種した。これを30
℃で2800 luxの人工光線照射下で育成し、10日後
の草丈および生体重を測定した。測定結果を第２
表に示した。
なお比較値は無処理区の測定結果を100とした
場合の値（％）を示す。[Table] The compound according to the present invention can be produced, for example, in the following manner. Production Example 1 Method for producing Compound No. 2 19.7 g of fumaric acid was suspended in 60 ml of water, and 10 g of sodium hydroxide dissolved in 15 ml of water was added with stirring. Next, add 9.3g of sodium tungstate and 20ml
30% hydrogen peroxide solution was added. First cool down,
Next, it was kept at 63-64°C for 1.5 hours while heating. PH
In order to keep the temperature above 4, a 0.5N aqueous sodium hydroxide solution was added dropwise. After the reaction was completed, most of the water was distilled off under reduced pressure, and the residue was poured into a large amount of acetone to obtain a sticky oily compound. Acetone was removed and fresh acetone was added. This operation was repeated twice to obtain crystals of Compound No. 2. Production Example 2 Method for producing Compound No. 3 Dissolve 22.5 g of compound No. 2 obtained in the same manner as Production Example 1 in the minimum amount of water, and add 40
When the mixture was stirred into 120 ml of a hot aqueous solution in which g of barium chloride was dissolved, Compound No. 3 was quantitatively obtained. Preparation Example 3 Method for Preparing Compound No. 6 25.5 g of Compound No. 3 was dissolved in 90 ml of dry methanol. Cool this to 10-15℃,
6.8 ml of concentrated sulfuric acid was added dropwise over 4 hours while stirring. After 12 hours, 3.6 g of anhydrous magnesium sulfate was added and the mixture was refluxed with stirring for 5 hours. 2.8 g of calcium carbonate was added, the methanol solution was filtered through a heating funnel, and the solvent was distilled off under reduced pressure to obtain 12.3 g of compound No. 6. Preparation Example 4 Method for Preparing Compound No. 55 0.8 g of Compound No. 6 was dissolved in 20 ml of methanol in an open beaker and 2.6 g of n-octylamine was added with vigorous stirring. The reaction mixture was first cooled, and when it became cloudy, it was stirred for another hour at room temperature, the solvent was distilled off, and then recrystallized from methanol to obtain compound no.
55 compounds were obtained. Production Example 5 Method for producing compound No. 5 11.6g of Compound No. 6 was mixed with 50% methanol.
ml, add 120 ml of methanol solution containing 4.6 g of potassium hydroxide, cool on ice, keep at the same temperature for 2 hours with stirring, then distill off the solvent, wash with methanol, and add 120 ml of methanol solution containing 4.6 g of potassium hydroxide. A compound No. 5 was obtained. Production Example 6 Method for producing compound No. 28 A mixture of 1.32 g of epoxysuccinic acid, 6.5 g of n-octyl alcohol, and 30 ml of sulfuric acid was
- Placed in Stark water separator and refluxed with benzene as solvent. After the reaction was completed, the reaction solution was washed with aqueous sodium bicarbonate, washed with water, dried, and the solvent was distilled off. Octyl alcohol was removed by vacuum distillation, and compound No. 28 was obtained from the 100% benzene effluent fraction by silica gel column chromatography (hexane-benzene). Production Example 7 Method for producing Compound No. 50 In an open beaker, 0.8 g of dimethyl succinate and 2 ml of cold aqueous ammonia were stirred for 15 minutes using a strong stirrer. The product was separated by filtration and washed with a small amount of water. 0.6 g of crude crystals of compound No. 50 were obtained. This was reconstituted from water to obtain 0.52 g of purified product. To prepare the agent of the present invention, for example, powder, aqueous solution,
It can be formulated into any conventional and known dosage forms such as emulsions, aqueous or oily suspensions. The amount of the agent of the present invention to be used varies depending on the type of crop, the growth stage of the crop, the method or time of use, etc., but in general, in the case of soil application, the amount of the compound, that is, the active ingredient, is 0.1 to 0.1 to 1000ppm, and when spraying as an aqueous solution on the foliage of crops, the active ingredient is 1-20000ppm, preferably 100-20000ppm.
Spray an aqueous solution with a concentration of 10000ppm. The agent of the present invention is generally used in the form of an aqueous solution, but it may also be mixed into the soil together with fertilizer, or it may be sprayed on the soil surface during top dressing. Furthermore, it is also possible to use it in combination with liquid fertilizers, insecticides, fungicides, foliar sprays, etc. It is preferable to spray an aqueous solution containing a surfactant in order to make it easier for the chemicals to adhere to and penetrate the crops. The agent of the present invention is generally preferably used during the period when the photorespiration of the plant is active, for example, from the reproductive growth period to the harvest period of the plant. However, depending on the crop, it may show more favorable effects when used during the vegetative growth period, so the timing of use is not particularly limited. Next, the effects of the present agent will be explained using test examples. Test Example 1 A Hoagland hydroponic solution in which the compound of the present invention was adjusted to a predetermined concentration was placed in a glass tube (φ2.3 cm x 15.8 cm) lined with paper, and immediately after germination, rice (variety: Nipponbare) was placed in it. Sowed 10 seeds each. This is 30
The plants were grown under artificial light irradiation at 2800 lux at ℃, and the plant height and fresh weight were measured 10 days later. The second measurement result
Shown in the table. Note that the comparison values are the values (%) when the measurement results of the untreated area are set as 100.
【表】【table】
【表】【table】
【表】【table】
【表】
試験例 ２
播種後約１ケ月生育した５葉期の水稲（品種・
日本晴）を直径が3.5cm、高さが14cmの容器に入
れ、所定濃度の本発明剤に係る化合物を溶解した
本村氏Ｂ液（PH５〜5.5）を与えて、30℃で10000
lux、長日条件下で生育させ、21日後の長さ、生
体重および乾物重量を測定した。結果を第３表に
示した。
なお測定値は無処理区の測定結果を100とした
場合の比較値（％）を示す。[Table] Test Example 2 Paddy rice (varieties/
Nipponbare) was placed in a container with a diameter of 3.5 cm and a height of 14 cm, and Motomura's solution B (PH 5 to 5.5) in which a compound related to the present invention agent at a predetermined concentration was dissolved was added, and the mixture was heated to 10,000 at 30°C.
lux, and were grown under long-day conditions, and the length, fresh weight, and dry weight were measured after 21 days. The results are shown in Table 3. The measured values are comparative values (%) when the measurement results of the untreated area are set as 100.
【表】【table】
Claims (1)
土金属、炭素数１〜12の直鎖状アルキル基、炭素
数３〜４の分枝状アルキル基、アリル基、イソペ
ンテニル基、炭素数３又は６の環状アルキル基、
フエニル基、ハロゲン置換フエニル基、ベンジル
基、ハロゲン置換ベンジル基、チエニル基置換メ
チル基、フリル基置換メチル基を示す）； （たゞしR3はＨ、炭素数１〜12の直鎖状アルキル
基、炭素数６の還状アルキル基、ハロゲン置換フ
エニル基、ベンジル基、R4はアルカリ金属を示
す）；又は （たゞしR5、R6はＨ、炭素数１〜12の直鎖状アル
キル基、アリル基、フエニル基、ベンジル基を示
す） で示される化合物から選ばれる１種又は２種以上
の化合物を有効成分として含有することを特徴と
する光呼吸阻害剤。[Claims] 1. General formula (R 1 and R 2 are H, alkali or alkaline earth metal, linear alkyl group having 1 to 12 carbon atoms, branched alkyl group having 3 to 4 carbon atoms, allyl group, isopentenyl group, carbon cyclic alkyl group of number 3 or 6,
phenyl group, halogen-substituted phenyl group, benzyl group, halogen-substituted benzyl group, thienyl-substituted methyl group, furyl-substituted methyl group); (R 3 is H, a linear alkyl group having 1 to 12 carbon atoms, a cyclic alkyl group having 6 carbon atoms, a halogen-substituted phenyl group, a benzyl group, and R 4 is an alkali metal); or (R 5 and R 6 each represent H, a linear alkyl group having 1 to 12 carbon atoms, an allyl group, a phenyl group, or a benzyl group) One or more compounds selected from the following: A photorespiration inhibitor characterized by containing as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4386579A JPS55136205A (en) | 1979-04-11 | 1979-04-11 | Photorespiration inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4386579A JPS55136205A (en) | 1979-04-11 | 1979-04-11 | Photorespiration inhibitor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55136205A JPS55136205A (en) | 1980-10-23 |
| JPS623801B2 true JPS623801B2 (en) | 1987-01-27 |
Family
ID=12675582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4386579A Granted JPS55136205A (en) | 1979-04-11 | 1979-04-11 | Photorespiration inhibitor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55136205A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0591686U (en) * | 1993-04-08 | 1993-12-14 | オリンパス光学工業株式会社 | Endoscope syringe |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4975459A (en) * | 1989-12-13 | 1990-12-04 | Rohm And Haas Company | Microbicidal and plant growth regulating compounds |
-
1979
- 1979-04-11 JP JP4386579A patent/JPS55136205A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0591686U (en) * | 1993-04-08 | 1993-12-14 | オリンパス光学工業株式会社 | Endoscope syringe |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55136205A (en) | 1980-10-23 |
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