JPH03361B2 - - Google Patents

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Publication number
JPH03361B2
JPH03361B2 JP19462082A JP19462082A JPH03361B2 JP H03361 B2 JPH03361 B2 JP H03361B2 JP 19462082 A JP19462082 A JP 19462082A JP 19462082 A JP19462082 A JP 19462082A JP H03361 B2 JPH03361 B2 JP H03361B2
Authority
JP
Japan
Prior art keywords
group
carbon atoms
tobacco
axillary bud
leaves
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
Application number
JP19462082A
Other languages
Japanese (ja)
Other versions
JPS5984803A (en
Inventor
Shoin Nagato
Mitsuhiko Katayama
Tetsuya Ogawa
Takeshi Inoi
Heitaro Obara
Yasuhiko Hamazaki
Toshuki Yamamoto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JNC Corp
Original Assignee
Chisso Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Chisso Corp filed Critical Chisso Corp
Priority to JP19462082A priority Critical patent/JPS5984803A/en
Publication of JPS5984803A publication Critical patent/JPS5984803A/en
Publication of JPH03361B2 publication Critical patent/JPH03361B2/ja
Granted legal-status Critical Current

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  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

【発明の詳細な説明】[Detailed description of the invention]

本発明はたばこの腋芽抑制剤に関する。 現在迄に、たばこの腋芽抑制作用を有する物質
は多数知られているが、実用に供されているのは
マレイン酸ヒドラジツドの塩類である。しかし、
マレイン酸ヒドラジツドは処理時期のある条件下
で頂葉に薬害を生ぜしめ、また抑制効果が不十分
な場合も生じる。更に、その塩の一部には、毒性
が心配されているものもある。 本発明者等は、新しいたばこの腋芽抑制剤を開
発すべく鋭意、研究の結果、ジニトロフエニル誘
導体がたばこの葉に対して薬害がなく、かつ、た
ばこの葉腋から発生する腋芽の成長に対して優れ
た抑制作用を有することを見出し、本発明に至つ
た。本発明の有効成分であるジニトロフエニル誘
導体は 一般式 (式中のR1は、次の(ア)〜(キ)のいずれか一つの
置換基を示し、 (ア) 炭素数1〜8の直鎖又は分岐のアルキル基、 (イ) 炭素数3または4のアルケニル基、 (ウ) プロパルギル基、 (エ) メトキシ基、1つ又は2つのエトキシ基、メ
トキシエトキシ基、もしくはフエニル基で置換
された炭素数2〜4のアルキル基、 (オ) シクロプロピルメチル基、 (カ) 炭素数5〜8のシクロアルキル基、 (キ) 第三ブチル基もしくは4−プロピルシクロヘ
キシル基で4−位を置換されたシクロヘキシル
基、 R2は、炭素数1〜5の直鎖又は分岐のアルキ
ル基又はシクロヘキシル基を示す)にて表わされ
る。 式()のこれらの化合物は例えば、ジヤーナ
ル・オブ・ケミカルソサイエテイ、2942〜2947頁
(1954年)に記載の方法等に準じて製造すること
ができる。 本発明はたばこの腋芽抑制剤は、通常の製剤技
術により、各種担体、増量剤、溶剤、界面活性
剤、安定剤等と配合して、例えば、水和剤、乳剤
等の形態に製剤化して使用することが望ましい。 また、本発明のたばこの腋芽抑制剤の使用量
は、たばこの品種、施用方法、施用時期により異
るが、式()の化合物量としては1アール当り
一般的に10〜1000gであり好ましくは30〜300g
である。 本発明のたばこの腋芽抑制剤の好ましい使用方
法としては、たばこの花房の摘芯後に、茎葉部中
心に噴霧処理することによりたばこの葉に薬害を
出さずに、しかも効果的に腋芽の発生を抑制する
ことができる。 参考例 (2,6−ジニトロ−4−t−ブチルフエニ
ル−n−プロピルエーテルの合成) 無水エタノール70mlに金属ナトリウム0.92gを
溶解し、4−t−ブチルフエノール6.0gを注加
したのち、n−プロピルクロライド3.5gを注加
し、20時間煮沸環流して反応させる。次いでエタ
ノールを減圧留去し、水を加えてベンゼンで抽出
し、3%苛性ソーダ溶液及び水で洗浄し、芒硝で
乾燥したのち溶媒を減圧留去し、残査を減圧蒸溜
すると、4−t−ブチル−n−プロポキシベンゼ
ン(沸点130〜131℃/19mmHg)6.5gが得られ
る。これを酢酸6mlに溶解し、0〜5℃で発煙硝
酸(比重1.5)12mlを注加したのち、20%発煙硫
酸12mlを注加し、1時間反応させ、次いで室温で
1時間、35〜40℃で40時間反応させる。反応終了
後、反応混合物を氷水に注加してクロロホルムで
抽出し、この抽出物を水、3%炭酸ソーダ溶液及
び水で洗浄し、芒硝で乾燥したのちクロロホルム
を留去し、残査をエタノールで再結晶すると、
2,6−ジニトロ−4−t−ブチルフエニル−n
−プロピルエーテル4.5g(融点106〜107℃)が
得られる。同様に操作して他の物質を合成した。
その融点、沸点あるいは性状を第1表に示す。 製剤例 1:乳剤 2,6−ジニトロ−4−sec−ブチルフエニ
ル−n−プロピルエーテル 20部 ヘキサン 20部 キシレン 45部 ソルポール900A(東邦化学工業製) 15部 各成分を均一に混合して乳剤となし、水で希釈
して使用する。 製剤例 2:水和剤 2,6−ジニトロ−4−iso−プロピルフエ
ニル−エチルエーテル 50部 珪藻土 25部 クレー 22部 ルノツクスR−1000C(東邦化学工業製) 3部 試験例 1:たばこの腋芽抑制効果試験 実生のたばこ苗(品種:ブライトイエロー)を
畑混合土(畑土:クレハ化学製畑培土:ピートモ
ス:鶏糞=2:2:1:1)を詰めた1/5000a
ワグネルポツトに移植する。 植物は温室内で生育させ、本葉が約10葉出揃つ
た時に本葉8〜9葉を残して摘芯する。本発明の
たばこの腋芽抑制剤として製剤例2にて調製した
水和剤を用い各有効成分の濃度を1000ppmおよび
4000ppmに調節し、摘心直後茎葉部へ噴霧する。
噴霧後は地上部からの散水は行わず、ポツト下部
の吸水孔よりの施水とし、温室内で20日間生育さ
せる。 試験終了後、全ての葉腋から、腋芽を採取し、
その重量を秤量し、その結果を無処理区から取つ
た腋芽重量と比較し、腋芽抑制率を下記の式によ
り算出し、第1表に示した。 腋芽抑制率= (無処理区の腋芽重量)−(処理区の腋芽重量)/(無
処理区の腋芽重量)× 100 なお、本試験期間中、本葉の葉色に変化は見ら
れなかつた。
The present invention relates to a tobacco axillary bud inhibitor. To date, many substances have been known to have an inhibitory effect on tobacco axillary buds, but the ones that have been put into practical use are salts of maleic acid hydrazide. but,
Maleic acid hydrazide can cause damage to the terminal leaves under certain conditions during treatment, and there are also cases where the inhibitory effect is insufficient. Furthermore, there are concerns about the toxicity of some of these salts. The present inventors conducted extensive research to develop a new tobacco axillary bud inhibitor and found that dinitrophenyl derivatives have no phytotoxicity to tobacco leaves and are effective against the growth of axillary buds that develop from the axils of tobacco leaves. The present inventors discovered that the present invention has a suppressive effect. The dinitrophenyl derivative which is the active ingredient of the present invention has the general formula (R 1 in the formula represents any one of the following substituents (a) to (g), (a) a linear or branched alkyl group having 1 to 8 carbon atoms, (b) 3 carbon atoms or 4 alkenyl group, (c) propargyl group, (d) methoxy group, alkyl group having 2 to 4 carbon atoms substituted with one or two ethoxy groups, methoxyethoxy group, or phenyl group, (o) cyclo Propylmethyl group, (f) cycloalkyl group having 5 to 8 carbon atoms, (g) cyclohexyl group substituted at the 4-position with tert-butyl group or 4-propylcyclohexyl group, R 2 is C 1 to 5 (represents a straight-chain or branched alkyl group or cyclohexyl group). These compounds of formula () can be produced, for example, according to the method described in Journal of Chemical Society, pages 2942-2947 (1954). The tobacco axillary bud suppressant of the present invention is prepared by compounding it with various carriers, fillers, solvents, surfactants, stabilizers, etc. in the form of hydrating powders, emulsions, etc. using conventional formulation techniques. It is desirable to use it. Further, the amount of the tobacco axillary bud inhibitor of the present invention to be used varies depending on the tobacco variety, application method, and application time, but the amount of the compound of formula () is generally 10 to 1000 g per are, and is preferably 30~300g
It is. A preferred method of using the tobacco axillary bud inhibitor of the present invention is to spray the tobacco center on the stem and leaves after core-picking the tobacco inflorescences, thereby effectively inhibiting axillary bud development without causing any chemical damage to the tobacco leaves. can do. Reference Example (Synthesis of 2,6-dinitro-4-t-butylphenyl-n-propyl ether) Dissolve 0.92 g of metallic sodium in 70 ml of absolute ethanol, add 6.0 g of 4-t-butylphenol, and then dissolve n-propyl ether. Add 3.5 g of propyl chloride and boil and reflux for 20 hours to react. Next, ethanol was distilled off under reduced pressure, water was added, extracted with benzene, washed with 3% caustic soda solution and water, dried over Glauber's salt, the solvent was distilled off under reduced pressure, and the residue was distilled under reduced pressure. 6.5 g of butyl-n-propoxybenzene (boiling point 130-131°C/19 mmHg) is obtained. Dissolve this in 6 ml of acetic acid, add 12 ml of fuming nitric acid (specific gravity 1.5) at 0 to 5°C, add 12 ml of 20% oleum, react for 1 hour, and then react for 1 hour at room temperature for 35 to 40 minutes. Incubate for 40 hours at °C. After the reaction was completed, the reaction mixture was poured into ice water and extracted with chloroform. The extract was washed with water, a 3% sodium carbonate solution and water, dried over Glauber's salt, the chloroform was distilled off, and the residue was dissolved in ethanol. When recrystallized with
2,6-dinitro-4-t-butylphenyl-n
- 4.5 g of propyl ether (melting point 106-107°C) are obtained. Other substances were synthesized in the same manner.
Their melting points, boiling points and properties are shown in Table 1. Formulation example 1: Emulsion 2,6-dinitro-4-sec-butylphenyl-n-propyl ether 20 parts Hexane 20 parts Xylene 45 parts Solpol 900A (manufactured by Toho Chemical Industries) 15 parts Each component is mixed uniformly to form an emulsion. , dilute with water and use. Formulation example 2: Wettable powder 2,6-dinitro-4-iso-propylphenyl-ethyl ether 50 parts diatomaceous earth 25 parts clay 22 parts Lunox R-1000C (manufactured by Toho Chemical Industries) 3 parts Test example 1: Tobacco axillary bud Suppression effect test Tobacco seedlings (variety: Bright Yellow) were packed with field mixed soil (field soil: Kureha Chemical field soil: peat moss: chicken manure = 2:2:1:1) 1/5000a
Transplant to Wagner pot. The plants are grown in a greenhouse, and when about 10 true leaves have appeared, the cores are pruned, leaving 8 to 9 true leaves. As the tobacco axillary bud suppressant of the present invention, the hydration powder prepared in Formulation Example 2 was used, and the concentration of each active ingredient was 1000 ppm and
Adjust to 4000ppm and spray on the stems and leaves immediately after pruning.
After spraying, water is not applied from above the ground, but rather from the water absorption hole at the bottom of the pot, and the plants are grown in a greenhouse for 20 days. After the test, axillary buds were collected from all leaf axils,
The weight was weighed, and the result was compared with the axillary bud weight taken from the untreated plot, and the axillary bud suppression rate was calculated using the following formula, and is shown in Table 1. Axillary bud suppression rate = (axillary bud weight in untreated area) - (axillary bud weight in treated area)/(axillary bud weight in untreated area) x 100 During this test period, no change was observed in the color of true leaves.

【表】【table】

【表】【table】

【表】 試験例 2 たばこの腋芽抑制試験 実生のたばこ苗(品種:ブライトイエロー)を
畑混合土(畑土:ピートモス:鶏糞=4:4:
1)を詰めた1/2000aワグネルポツトに移植し
畑混合土(畑土:ピートモス:鶏糞=4:4:
1)を詰めた1/2000aワグネルポツトに移植し
た。 植物は温室内で2ケ月間生育させ草丈約1mの
時期に本葉14〜15葉を残して摘芯する。摘芯2日
後に製剤例1で製剤した薬剤を処理濃度に希釈
し、ポツト当り200ml/株を茎部を中心に噴霧処
理した。 処理後ポツトを温室内に置き、25日間ポツト下
部の吸水孔より施水して生育させた。 試験終了後、すべての本葉、および腋芽を採取
し、一週間風乾した後、その風乾重量を秤量し、
その結果を、無処理区の風乾重量と比較し、試験
例1に示した計算式により腋芽抑制率を算出し、
第2表に示した。
[Table] Test Example 2 Tobacco axillary bud suppression test Seedling tobacco seedlings (variety: Bright Yellow) were mixed with field soil (field soil: peat moss: chicken manure = 4:4:
1) into a 1/2000a Wagner pot filled with field mixed soil (field soil: peat moss: chicken manure = 4:4:
I transplanted it into a 1/2000a Wagner pot filled with 1). The plants are grown for two months in a greenhouse, and when the plants reach a height of about 1 m, the cores are removed, leaving 14 to 15 true leaves. Two days after core removal, the drug prepared in Formulation Example 1 was diluted to a treatment concentration, and 200 ml/plant was sprayed onto each pot, focusing on the stems. After treatment, the pots were placed in a greenhouse and watered through the water absorption holes at the bottom of the pots for 25 days to grow. After the test, all true leaves and axillary buds were collected, air-dried for one week, and their air-dried weight was weighed.
The results were compared with the air-dried weight of the untreated area, and the axillary bud suppression rate was calculated using the formula shown in Test Example 1.
It is shown in Table 2.

【表】 試験例 3:たばこに対する薬害および腋芽抑制
試験 実生のたばこ苗(品種:ブライトイエロー)を
畑混合土(畑土:クレハ化学製畑培土:ピートモ
ス:鶏糞=2:2:1:1)を詰めた1/5000a
ワグネルポツトに移植する。 移植したたばこは温室内で生育させ草丈50〜60
cmの時期に本葉7〜8葉を残して摘心する。本発
明の腋芽抑制剤は摘心2日後に茎を中心に所定の
濃度の懸濁液を噴霧した。 噴霧処理後、供試植物はポツト下部の吸水孔よ
り流水し、温室内で2週間生育させた。 試験終了後、摘心部から下部の5葉を採取し、
その生体重を秤量し、無処理区および対照薬剤区
の生体重と比較した。 さらに、葉色および腋芽抑制効果は肉眼観察に
より調査し、第3表に示した。
[Table] Test Example 3: Tobacco toxicity and axillary bud suppression test Tobacco seedlings (variety: Bright Yellow) were grown in mixed field soil (field soil: Kureha Chemical field soil: peat moss: chicken manure = 2:2:1:1) 1/5000a packed with
Transplant to Wagner pot. The transplanted tobacco is grown in a greenhouse and the plant height is 50-60cm.
At the cm stage, pinch the leaves leaving 7 to 8 true leaves. A suspension of the axillary bud inhibitor of the present invention at a predetermined concentration was sprayed on the stems two days after the stems were pruned. After the spray treatment, the test plants were grown in a greenhouse for two weeks with water flowing through the water absorption hole at the bottom of the pot. After the test, collect the lower five leaves from the pinched part,
The live weight was weighed and compared with the live weight of the untreated group and the control drug group. Furthermore, leaf color and axillary bud suppression effect were investigated by visual observation and are shown in Table 3.

【表】【table】

Claims (1)

【特許請求の範囲】 1 一般式 (式中のR1は次の(ア)〜(キ)のいずれか一つの置
換基を示し、 (ア) 炭素数1〜8の直鎖又は分岐のアルキル基、 (イ) 炭素数3または4のアルケニル基、 (ウ) プロパルギル基、 (エ) メトキシ基、1つ又は2つのエトキシ基、メ
トキシエトキシ基、もしくはフエニル基で置換
された炭素数2〜4のアルキル基、 (オ) シクロプロピルメチル基、 (カ) 炭素数5〜8のシクロアルキル基、 (キ) 第三ブチル基もしくは4−プロピルシクロヘ
キシル基で4−位を置換されたシクロヘキシル
基、 R2は、 炭素数1〜5の直鎖又は分岐のアルキル基、又
はシクロヘキシル基を示す)で表されるジニトロ
フエニル誘導体を有効成分として含有することを
特徴とするたばこの腋芽抑制剤。
[Claims] 1. General formula (R 1 in the formula represents any one of the following substituents (a) to (g), (a) a linear or branched alkyl group having 1 to 8 carbon atoms, (b) 3 or 4 alkenyl group, (c) propargyl group, (d) methoxy group, alkyl group having 2 to 4 carbon atoms substituted with one or two ethoxy groups, methoxyethoxy group, or phenyl group, (o) cyclopropyl methyl group, (f) a cycloalkyl group having 5 to 8 carbon atoms, (g) a cyclohexyl group substituted at the 4-position with a tert-butyl group or 4-propylcyclohexyl group, R 2 is a cycloalkyl group having 1 to 5 carbon atoms; 1. A tobacco axillary bud inhibitor comprising a dinitrophenyl derivative represented by a straight-chain or branched alkyl group or a cyclohexyl group as an active ingredient.
JP19462082A 1982-11-08 1982-11-08 Tobacco axillary bud inhibitor Granted JPS5984803A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP19462082A JPS5984803A (en) 1982-11-08 1982-11-08 Tobacco axillary bud inhibitor

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP19462082A JPS5984803A (en) 1982-11-08 1982-11-08 Tobacco axillary bud inhibitor

Publications (2)

Publication Number Publication Date
JPS5984803A JPS5984803A (en) 1984-05-16
JPH03361B2 true JPH03361B2 (en) 1991-01-07

Family

ID=16327554

Family Applications (1)

Application Number Title Priority Date Filing Date
JP19462082A Granted JPS5984803A (en) 1982-11-08 1982-11-08 Tobacco axillary bud inhibitor

Country Status (1)

Country Link
JP (1) JPS5984803A (en)

Also Published As

Publication number Publication date
JPS5984803A (en) 1984-05-16

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