JPS59231068A - Acid amide compound and its preparation - Google Patents
Acid amide compound and its preparationInfo
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- JPS59231068A JPS59231068A JP10623383A JP10623383A JPS59231068A JP S59231068 A JPS59231068 A JP S59231068A JP 10623383 A JP10623383 A JP 10623383A JP 10623383 A JP10623383 A JP 10623383A JP S59231068 A JPS59231068 A JP S59231068A
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- Indole Compounds (AREA)
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Abstract
Description
【発明の詳細な説明】
本発明は植物病原菌による土壌病害に対して優れた防除
効果を有する酸イミド系化合物およびその製造法に関す
る。さらに詳しくは本発明は一般式［Ｉ］
〔式中、ＸおよびＹは同一または相異なり、酸素原子ま
たは硫黄原子を表わす。Ｚは低級アルキレン基、低級シ
クロアルキレン基、低級シクロアルケニレン基またはア
リーレン基を表わすか、ハロゲン原子、カルボキシル基
またはフェニル基で置換されていてもよ０低級アルケニ
レン基を表わす。ｎは１．２．８または４を表わす。た
だし、ＸおよびＹがともに酸素原子であり、かつｎが２
であるとき、Ｚ ハｏ −フェニレン基ではない。〕で
示される酸イミド系化合物（以下、本発明化合物と記す
。）およびその製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an acid imide compound having an excellent control effect on soil diseases caused by plant pathogens and a method for producing the same. More specifically, the present invention is based on the general formula [I] [wherein X and Y are the same or different and represent an oxygen atom or a sulfur atom. Z represents a lower alkylene group, a lower cycloalkylene group, a lower cycloalkenylene group or an arylene group, or a lower alkenylene group which may be substituted with a halogen atom, a carboxyl group or a phenyl group. n represents 1.2.8 or 4. However, both X and Y are oxygen atoms, and n is 2
, Z is not a o -phenylene group. The present invention relates to an acid imide compound (hereinafter referred to as the compound of the present invention) represented by the following formula and a method for producing the same.
土壌中に存在する植物病原菌が植物に感染し多大の被害
を与える土壌病害は最も防除が困難な植物病害の一つで
あり、従来クロルピクリン、臭化メチル等の土壌燻蒸剤
やベノミノル、ヒドロキシイソキサゾール等の殺菌剤が
防除のため除のために特別な労力を要することなどの点
で必ずしも充分なものではない。Soil diseases, in which plant pathogenic bacteria present in the soil infect plants and cause great damage, are among the most difficult plant diseases to control. Bactericidal agents such as ZOL are not necessarily sufficient for controlling the pests, as they require special effort for removal.
このような状況のもとで、本発明者らは土壌病害防除剤
の開発について鋭意検討を重ねた結果、本発明化合物が
多くの植物病原菌による土Ｈ病害に対し優れた防除効果
を有することを見いだした。Under these circumstances, the present inventors have conducted extensive studies on the development of soil disease control agents, and have found that the compounds of the present invention have excellent control effects against soil H diseases caused by many plant pathogens. I found it.
本発明化合物が優れたＶｊ除効果を有する植物病原菌に
は、フザリウム属のトマト萎凋病菌（Ｆｕｓａｒｊｕｒ
ｎ ｏｘｙｓｐｏｒｕｍ ｆ＋ｓｐ、 ｌ１ｃｏｐｏｒ
ｓｉｃｉ ）、ダイコン萎黄病菌（Ｆ＋ｔｓａｒｉｕｒ
ｎ ｏｘｙｓｐｏｒｕｍ ｆ＋ｓｐ、ｒａｐｈａｎｉ
）、キュウリ蔓割病菌（Ｆｕｓａｒｉｕｍ ｏｘｙｓｐ
ｏｒｕｍ ｆ、ｓｐ。Plant pathogenic bacteria for which the compound of the present invention has an excellent Vj eliminating effect include tomato wilt fungus belonging to the genus Fusarium.
no oxysporum f+sp, l1copor
sici), radish chlorosis fungus (F+tsariur
no oxysporum f+sp, raphani
), cucumber oxysp
orum f, sp.
ｃｕｃｕｍｅｒｉｎｕｍ ）、スイカ蔓割病５１４ （
Ｆｕｓａｒｉｕｍ ｏｘｙｓｐｏｒｕｍｆ、 ｓｐ、
ｎｉｖＣｕｍ ）、キャベツ萎黄病菌（Ｆｕｓａｒｉｕ
ｍｏｘｙｓｐｏｒｕｒｎ ｒ、ｓｐ、ｃｏｎｇＬ＋ｔｉ
ｎａｎｓ ）、イチゴ萎黄病閑（Ｉ’ｕｓａｒｉｕｍ
ｏｘｙｓｐｎｒｕｍ ｆ’−ｓｐ、 ｆｒａｇａｒｉａ
ｅ ）、コムギ紅色雪質病菌（Ｆｕｓａｒｉｕｍ ｎ１
ｖａｌｅ ｆ、 ｓｐ＋ｇｒａｎ］１ｎｊｃｏｌａ ）
、コムギ赤黴病菌（Ｆｕｓａｒｉｕｍ ｒｏ！Ｉｃｕｍ
「、 ｓｐ、 ｃｏｒｅａｌｉｓ）、エントウ根腐病
函（１’ｕｓａｒｉｕｒｎ ５ｏｌａｎｉ ｆ、 ｓｐ
−ｐｉｓｉ ）、ピシウム属のキュウリ苗立枯病菌（Ｐ
ｆｔｈｉｕｍａｐｈａｎｉｄｅｒｒｒ！ｏｆ、ｕｍ ）
、タバコ苗立枯病菌（Ｐｙｔ、ｈｉｕｍｄｅｂａｒｙａ
ｎｕｍ ）、リゾクトニア属のキュウリｔ１１−立枯病
菌・ジャカイモ！Ａ７病菌・テンサイ根腐病菌・シバ葉
音病菌・タバコ腰折病＠ （Ｒｈ１ｚｏｃｔｏｎｊａｓ
ｏｌａｎｉ ）、−１ｉ−ンサイ立枯病菌（几ｈｉｚｏ
ｃｔｎｎｉａ ｃａｎｒＨｄａ）、ダ４ズ炭腐病菌（Ｒ
ｂ１ｚｏｃｔｏｎｉａ ｂａｔａｔｉｃｏｌａ ）、パ
ーティシイリューム属のナス半身萎凋病菌・ノ１クサ白
絹病菌・チャ白組病菌（Ｃｏｒｔｉｃｉｕｒ＋＋ ｒｏ
ｌｆｓｊｉ ）、ティフラ属のコムキ雪腐菌核病菌・ア
ルファルフｙＭ腐小粒菌核病菌（ＴｙｐｂｕＪａ １ｎ
ｃａｒｎａｔａ 、 Ｔｙｐｈｕｌａｉｓｈｉｋａｒｉ
ｅｎｓｉｓ ）、ブラズモディオフォーラ属のハクサイ
根瘤病菌・キャベツ根瘤病＠：ｊ（）’Ｉａｓｍｏｄｉ
ｏｐｈｏｒａｂｒａｓｓｉｃａｅ ）等がある。cucumerinum), watermelon vine split disease 514 (
Fusarium oxysporumf, sp.
nivCum), Cabbage chlorosis fungus (Fusariu
moxysporurn r, sp, congL+ti
nans), strawberry yellowing disease (I'usarium)
oxyspnrum f'-sp, fragaria
e), wheat fusarium n1
Vale f, sp+gran]1njcola)
, Fusarium ro!Icum
", sp.
-pisi), cucumber seedling blight fungus of the genus Pythium (P
fthiumaphaniderrr! of, um)
, tobacco seedling damping-off fungus (Pyt, hiumdebarya)
num ), Rhizoctonia cucumber t11- damping-off fungus, potato! A7 disease fungus, sugar beet root rot disease fungus, Shiba leaf sound disease fungus, tobacco hip buckling disease @ (Rh1zoctonjas
olani),
ctnnia canrHda), Da4zu charcoal rot fungus (R
b1zoctonia bataticola), eggplant half-wilt fungus, Corticiur++ ro
lfsji), TypbuJa 1n, Alfalf yM small-grain sclerotide fungus (TypbuJa 1n
carnata, Typhulaishikari
ensis ), Chinese cabbage root-knot fungus and cabbage root-knot fungus of the genus Blasmodiophora @:j()'Iasmodi
ophorabrassicae), etc.
従って、本発明化合物は畑地、水田、果樹園、茶畑、桑
畑、牧草地、芝生、！ｔｌＩ等の土壌病害防除剤の有効
成分として用いることができる。Therefore, the compound of the present invention can be used in fields, paddy fields, orchards, tea plantations, mulberry fields, pastures, lawns, etc. It can be used as an active ingredient of soil disease control agents such as tlI.
上記一般式［Ｉ）で示される本発明に係る酸イミド系化
合物において、アリーレン基としては、たとえば０−フ
ェニレン基ナフチレフ基またはる基などが挙げられる。In the acid imide compound according to the present invention represented by the above general formula [I], examples of the arylene group include 0-phenylene group, naphthylev group, and Ru group.
次に、本発明に係る酸イミド系化合物の製造法について
述べる。Next, a method for producing an acid imide compound according to the present invention will be described.
本発明の酸イミド糸化合物は、一般式［１］〔式中、Ｘ
、Ｙお６（び２は前記と同じである。〕で示される化合
物とを溶媒中、１００〜］、 ８０°Ｃ１好ましく １
．ｔ １８０〜１６０ ”Ｃ−Ｃ’ １〜８０時間反応
させることによりｆＭ造することができる。The acid imide thread compound of the present invention has the general formula [1] [wherein X
, Y6 (and 2 are the same as above) in a solvent at 100~], 80°C1 preferably 1
．． t 180-160 "C-C' fM can be produced by reacting for 1-80 hours.
また、本発明化合物は、一般″式〔■コ（）
υ
〔式中、２およびｎは前記と同じである。〕で示される
化合物と１または２当量の三硫化リンとを溶媒中、２５
〜１５０℃、１〜２４時間反応させることによっても製
造できる。なお、一般式［ｙ］で示される化合物は前述
の製造法により得られる。In addition, the compound of the present invention can be prepared by combining a compound represented by the general formula [■co() υ [where 2 and n are the same as above] and 1 or 2 equivalents of phosphorus trisulfide in a solvent,
It can also be produced by reacting at ~150°C for 1 to 24 hours. Incidentally, the compound represented by the general formula [y] can be obtained by the above-mentioned production method.
上記製造法において、一般式［Ｕで示される化合物とし
ては、たとえばコハク酸、１．２−シクロヘキサンジカ
ルボン酸、マレイン酸、イタコン酸、シトラコン酸、イ
゛ノブロピリデンコハク酸、８，４．５．６−チトラヒ
ドロフタル酸、メリメット酸、４−カルボキシフタル酸
、ジクロロマレイン酸、フェニルマレイン酸、テトラク
ロロフタル酸、テトラブロモフタル酸、４−ニトロフタ
ル酸、１．２−ピリジンジカルボン酸、８，４−フラン
ジカルボン酸、グルタル酸、２．２−ジメチルグルクン
酸、３，４−ピラジンジカルボン酸、８．８−ジメチル
グルタル酸、ジメチルマレイン酸、フタル酸、ナフタル
酸、１．２−シクロブタンジカルボン酸、モノクロロマ
レイン酸、モノブロモマレイン酸等の無水物がある。In the above production method, examples of the compound represented by the general formula [U include succinic acid, 1,2-cyclohexanedicarboxylic acid, maleic acid, itaconic acid, citraconic acid, isopropylidene succinic acid, 8,4. 5.6-titrahydrophthalic acid, melimetic acid, 4-carboxyphthalic acid, dichloromaleic acid, phenylmaleic acid, tetrachlorophthalic acid, tetrabromophthalic acid, 4-nitrophthalic acid, 1.2-pyridinedicarboxylic acid, 8 , 4-furandicarboxylic acid, glutaric acid, 2,2-dimethylgluconic acid, 3,4-pyrazinedicarboxylic acid, 8,8-dimethylglutaric acid, dimethylmaleic acid, phthalic acid, naphthalic acid, 1,2-cyclobutanedicarboxylic acid There are acids, anhydrides such as monochloromaleic acid and monobromomaleic acid.
また、浴媒には、ヘキサン、ヘプタン、リグロイン、石
油エーテル等の脂肪族炭化水素、ベンゼン、トルエン、
キシレン等の芳香族炭化水素、クロロホルム、四塩化炭
素、ジクロロエタン、クロロベンゼン、ジクロロベンセ
ン等のハｏ ケン化Ｒ化水素、ジエチルエーテル、ジイ
ソプロピルエーテル、ジオキサン、テトラヒドロフラン
、ジエチレングリコールジメチルエーテル等（１） エ
ーテル、蟻酸、酢酸、オレー（：、／酸等のｍｌ ＩＪ
Ｉ ｅ 、メタノール、エタノール、イソプロパツール
、ｔ−ブタノール、オクタツール、シクロヘキサノール
、メチルヤロ゛ノルブ、ジエチレングリコール、グリセ
リン等のアルコール、ニトロエタン、ニトロベンゼン等
のニトロ化物、アセトニトリル、イソブチロニトリル等
のニトリル、ピリジン、トリスチルアミン、Ｎ、Ｎ−ジ
エチルアニリン、トリフチルアミン、Ｎ−メチルモルホ
リン等の第三級アミン、ジメチルスルホキシド、スルホ
ラン等の硫黄化合物、水等、あるいはそれらの混合物が
ある。In addition, the bath medium includes aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, benzene, toluene,
Aromatic hydrocarbons such as xylene, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, hao such as dichlorobenzene, R hydrogen saponide, diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, etc. (1) Ether, formic acid, Acetic acid, Ole(:,/acid etc. ml IJ
Ie, alcohols such as methanol, ethanol, isopropanol, t-butanol, octatool, cyclohexanol, methyl alcohol, diethylene glycol, glycerin, nitrides such as nitroethane and nitrobenzene, nitrites such as acetonitrile and isobutyronitrile, Examples include tertiary amines such as pyridine, tristylamine, N,N-diethylaniline, triphthylamine, and N-methylmorpholine, sulfur compounds such as dimethylsulfoxide and sulfolane, water, and mixtures thereof.
反応終了後は、通常の後処理を行い、必要ならば、クロ
マトグラフィー、蒸留、再結晶等によって精製する。After the reaction is completed, usual post-treatments are carried out, and if necessary, purification is carried out by chromatography, distillation, recrystallization, etc.
次に本発明化合物の製造例を示す。Next, production examples of the compounds of the present invention will be shown.
製造例１ （本発明化合物（１）の製造）２−シクロへ
キセニルアミン（０，９７Ｆ）、無水コハク酸（１，０
ｇ）および酢酸（１０ｍｊ）の混合物を２４時間加熱還
流した。冷却後、反応混合物にエーテル（１０ｍＡ）を
加え、飽和炭酸水素ナトリウム水溶液、水飽和食塩水の
順に洗った。有機層を無水硫酸マグネシウムで乾燥し、
濃縮した。このようにして得られる油状物をシリカゲル
カラムクロマトグラフィーにより精製して、Ｎ−（２−
シクロへキセニル）コハク酸イミ・ド１．０７Ｆを得り
。Production Example 1 (Production of Compound (1) of the Present Invention) 2-cyclohexenylamine (0,97F), succinic anhydride (1,0
A mixture of g) and acetic acid (10mj) was heated under reflux for 24 hours. After cooling, ether (10 mA) was added to the reaction mixture, and the mixture was washed successively with a saturated aqueous sodium bicarbonate solution and a saturated brine solution. The organic layer was dried with anhydrous magnesium sulfate,
Concentrated. The oil obtained in this way was purified by silica gel column chromatography and N-(2-
cyclohexenyl) succinimide 1.07F was obtained.
ｎ２８°” １．５１９２
製造例２ （本発明化合物（２）の製造）２−シクロへ
キセニルアミン（０，９７ｆ）、無水マレイン酸（０，
９８Ｆ）、酢酸（１０ｔｄ）の混合物を２４時間加熱還
流した。製造例１と同様に後処理をして、Ｎ−（２−シ
クロへキセニル）マレイン酸イミド１．０６ｇを得た。n28°" 1.5192 Production Example 2 (Production of Compound (2) of the Invention) 2-cyclohexenylamine (0,97f), maleic anhydride (0,
A mixture of 98 F) and acetic acid (10 td) was heated under reflux for 24 hours. Post-treatment was carried out in the same manner as in Production Example 1 to obtain 1.06 g of N-(2-cyclohexenyl)maleic acid imide.
ｎ２ニーｓ ｔ、 ５２１１
製造例８ （本発明化合物（８）の製造）Ｎ−２−シク
ロへキナニル−８，４，５，６，−テトラヒドロフタル
イミド（８，５４１，１５，８ミリモル）、五硫化リン
（８，４０９，１５，８ミリモル）およびトルエン（１
０ｍｇ）の混合物を５時間加熱還流した。反応混合物を
冷却後、水にあけ、エーテルを加えて抽出した。n2nee st, 5211 Production Example 8 (Production of the present compound (8)) N-2-cyclohequinanyl-8,4,5,6-tetrahydrophthalimide (8,541,15,8 mmol), Phosphorus sulfide (8,409,15,8 mmol) and toluene (1
(0 mg) was heated under reflux for 5 hours. After cooling the reaction mixture, it was poured into water and extracted with ether.
有機層を無水硫酸マグネシウムで乾燥し、濃縮した。得
られる油状液体をシリカゲルクロマトグラフィーにより
精製し、本発明化合物（８）１．５１Ｆを得た。融点４
５〜４８°にのような製造法によって製造できる本発明
化合物のいくつかを第１表に示す。The organic layer was dried over anhydrous magnesium sulfate and concentrated. The obtained oily liquid was purified by silica gel chromatography to obtain the present compound (8) 1.51F. Melting point 4
Table 1 shows some of the compounds of the invention that can be prepared by methods such as 5-48°.
第 １ 表
次に、本発明化合物が土壌病害防除剤の有効成分として
有用であることを参考例で示す。なお、本発明化合物は
第１表の化合物番号で示し、比較対照に用いた化合物は
第２表の化合物記号で示す。Table 1 Next, reference examples show that the compounds of the present invention are useful as active ingredients of soil disease control agents. The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols in Table 2.
第 ２ 表
また、防除効力は調査時の供試植物の発病状態すなわち
葉、茎、根等の菌叢、病徴の程度を肉眼観察し、菌叢、
病徴が全く認められない供試植物数（以下、健ｍ数と記
す。）について。Table 2 In addition, the control efficacy was determined by visually observing the diseased state of the test plants at the time of the survey, that is, the bacterial flora on leaves, stems, roots, etc., and the degree of disease symptoms.
Regarding the number of test plants showing no disease symptoms (hereinafter referred to as the number of healthy plants).
化合物を供試した場合（以下、処理区の健苗数と記す。When a compound is tested (hereinafter referred to as the number of healthy seedlings in the treatment area).
）と、化合物を供試せずかつ病原菌を全く接種していな
い場合（以下、無処理、無接種名の健苗数と記す。）と
をそれぞれ数え、次式に従って健苗率（％）を求めてそ
の数値で示す。) and when no compound was tested and no pathogens were inoculated (hereinafter referred to as the number of healthy seedlings with no treatment or no inoculation), and the healthy seedling rate (%) was calculated according to the following formula. It is shown in numerical value.
試験例１ ダイコン萎黄病防除効果試験プラスチック
ポットに畑地土壌とダイコン萎黄病菌を培養した病原土
壌を良く混合して詰めた。ダイコン（品種：早生４０日
）を１５粒播種し覆土した。その後、水和剤にした供試
化合物の所定量を水で希釈し、土＃！潅注した。温室内
で８週間育成し、防除効力を調査した。Test Example 1 Test for effectiveness in controlling radish yellowing disease Upland soil and pathogenic soil in which radish yellowing fungi had been cultured were mixed well and packed in plastic pots. 15 seeds of Japanese radish (variety: 40 days early) were sown and covered with soil. After that, a predetermined amount of the test compound made into a hydrating powder was diluted with water, and soil #! Irrigated. The plants were grown in a greenhouse for 8 weeks and their pesticidal efficacy was investigated.
結果を第３表に示す。The results are shown in Table 3.
第 ３ 表
参考例２ キャベツ萎黄病防除効果
プラスチックポットに畑地土壌、キャベツ養苗病−を培
養した病原土壌および微粒剤にした供試化合物の所定量
を良く混合して詰めた。なお、クロルピクリンは畑地土
壌と病原土壌を良く混合して詰めた後、その所定量を注
入し、ビニール被覆して１週間放置し、ビニール被覆を
除去して、さらに１週間ガス抜きをした。キャベツ（品
種二四季穫）を１０粒播種し覆土した。温室内で８週間
育成し、防除効力を調査した。Table 3 Reference Example 2 Effect on controlling cabbage chlorotic disease Field soil, pathogenic soil in which cabbage seedling disease was cultured, and a predetermined amount of a test compound made into fine granules were thoroughly mixed and packed in a plastic pot. In addition, after chloropicrin was packed by thoroughly mixing upland soil and pathogenic soil, a predetermined amount of the mixture was injected, covered with vinyl and left for one week, the vinyl coating was removed, and gas was degassed for another week. Ten seeds of cabbage (variety: Nishiki Haru) were sown and covered with soil. The plants were grown in a greenhouse for 8 weeks and their pesticidal efficacy was investigated.
結果を第４表に示す。The results are shown in Table 4.
第 ４ 表
参考例８ キュウリ蔓割病防除効果
プラスチックポットに畑地土壊を詰め、キュウリ蔓割病
菌を＠養した病原土壌と粉剤にした供試化合物の所定量
を表層５ｃｍの深さまで良く混合して詰めた。Table 4 Reference Example 8 Effect on controlling cucumber bulrush blight A plastic pot was filled with field soil, and the pathogenic soil in which cucumber bulwark blight was cultivated and the specified amount of the test compound made into powder were thoroughly mixed to a depth of 5 cm from the surface layer. I packed it.
なお、比較対照化合物Ｃは畑地土壊を詰めたポットに所
定量を水で希釈して潅注した。キュウリ（品種二Ｎ不知
地這ンをＩＱｌ！２播Ｅ１シ覆土した。温室内で３週間
育成し、防除効力を調査した。A predetermined amount of Comparative Compound C was diluted with water and poured into a pot filled with field soil. Cucumber (variety 2N Shiranjikin) was sown with IQl!2 and covered with soil in E1. It was grown in a greenhouse for 3 weeks and its pesticidal efficacy was investigated.
結果を第５表に示す。The results are shown in Table 5.
第 ５ 表
試験例４ トマト萎ちょう病防除効果
乳剤にした供試化合物を水で希釈して所定濃度にし、そ
れを、プラスチックボットで育成した８葉期のトマト苗
（品種：福寿２号）の葉面に充分付着するように散布し
た。散布後、トマト萎ちょう病菌の胞子懸濁液を根元に
潅注した。接種夜温室内で３週間育成、防除効力を調査
した。Table 5 Test Example 4 Tomato wilt disease control effect A test compound made into an emulsion was diluted with water to a specified concentration, and it was applied to 8-leaf tomato seedlings (variety: Fukuju No. 2) grown in a plastic bot. It was sprayed so that it adhered sufficiently to the leaf surface. After spraying, a spore suspension of tomato wilt fungus was irrigated at the roots. The seeds were grown for 3 weeks in a greenhouse on the night of inoculation, and the control efficacy was investigated.
結果を第６表に示す。The results are shown in Table 6.
第 ６ 表
試験例５ ナス半身萎ちょう病防除効果ナス半身萎ちょ
う病菌を培養した銀培地を１区（２ｍ’）あたり１００
ｆ！接種し、微粒剤にした供試化合物の所定量を土壌に
混和した。Table 6 Test Example 5 Effect on controlling eggplant half-body wilt disease 100 g
f! A predetermined amount of the test compound that was inoculated and made into fine granules was mixed into the soil.
なお、クロルピクリンは、病原菌を接種後、その所定量
を注入しビニール被覆して１週間放置し、ビニール被覆
を除去して耕耘し、さらに１週間ガス抜きをした。その
後、２葉期のナス（品種：千両２号）を１区あたり１６
本移植し、温室内で約６週間育成し、防除効力を調査し
た。For chloropicrin, after inoculating pathogenic bacteria, a predetermined amount of the same was injected, covered with vinyl, left for one week, removed the vinyl coating, cultivated, and degassed for another week. After that, two-leaf eggplants (variety: Senryo 2) were added at 16 per section.
The plants were transplanted and grown in a greenhouse for about 6 weeks, and their pesticidal efficacy was investigated.
結果を第７表に示す。The results are shown in Table 7.
第 ７ 表
試験例６ ハクサイ根瘤病防除効果
プラスチックポットｌζ畑地土壌を詰め、ハクサイ根瘤
病菌で汚染された土壌と粉剤にした供試化合物の所定員
を表層５Ｇの深さまで良く混合して詰めた。ハクサイ（
品種：耐病６０日）を１５粒播種し覆土した。温室内で
４週間育成し、防除効力を調査した。Table 7 Test Example 6 Effect on Chinese cabbage root-knot control A plastic pot was filled with field soil, and soil contaminated with Chinese cabbage root-knot bacteria and a predetermined amount of powdered test compound were mixed well to a depth of 5G on the surface layer. Chinese cabbage (
15 seeds of cultivar: disease resistant (60 days) were sown and covered with soil. The plants were grown in a greenhouse for 4 weeks and their pesticidal efficacy was investigated.
結果を第８表に示す。The results are shown in Table 8.
第 ８ 表 第１頁の続き ・ヰ発 明 者 佐々木満 宝塚市高司４丁目２番１号住友 化学工業株式会社内 、ｎ・発 明 者 平田直則 宝塚市高司４丁目２番１号住友 化学工業株式会社内 −６９：Table 8 Continuation of page 1 ・Inventor: Mitsuru Sasaki Sumitomo 4-2-1 Takashi, Takarazuka City Within Kagaku Kogyo Co., Ltd. , n. Founder: Naonori Hirata Sumitomo 4-2-1 Takashi, Takarazuka City Within Kagaku Kogyo Co., Ltd. -69:
Claims (3)
たは硫黄原子を表わす。２は低級アルキレン基、低級シ
クロアルキレン基、低級シクロアルケニレン基またはア
リーレン基を表わすか、ハロゲン原子、カルボキシル基
またはフェニル基で置換されていてもよい低級アルケニ
レン基を表わす。ｎは１．２．８または４を表わす。た
だし、ＸおよびＹがともに酸素原子であり、かつｎが２
であるとき、２はＯ−フェニレン基ではない。］ で示される酸イミド系化合物。(1) General formula [wherein X and Y are the same or different and represent an oxygen atom or a sulfur atom. 2 represents a lower alkylene group, a lower cycloalkylene group, a lower cycloalkenylene group, or an arylene group, or a lower alkenylene group optionally substituted with a halogen atom, a carboxyl group, or a phenyl group. n represents 1.2.8 or 4. However, both X and Y are oxygen atoms, and n is 2
When 2 is not an O-phenylene group. ] An acid imide compound represented by:
るシクロアルヶニルアＥ ン（！： −般式〔式中、Ｘ
およびＹは同一または相異なり、酸素原子または硫黄原
子を表わす。２は低級アルキレン基、低級シクロアルキ
レン基、低級シクロアルケニレン基またはアリーレン基
を表わすか、ハロゲン原子、カルボキシル基またはフェ
ニル基で置換されていてもよい低級アルケニレン基を表
わす。ただし、ＸおよびＹがともに酸素原子であり、か
つｎが２であるとき、２は０−フェニレン基ではない。 ］ で示される化合物とを反応させることを特徴とする一般
式 〔式中、ｘ、ｙ、ｚおよびｎは前記と同じである。〕 で示される酸イミド系化合物の製造法。(2) General formula [where n represents 1.2.8 or 4]. ] Cycloalganyluane E (!: - general formula [wherein, X
and Y are the same or different and represent an oxygen atom or a sulfur atom. 2 represents a lower alkylene group, a lower cycloalkylene group, a lower cycloalkenylene group, or an arylene group, or a lower alkenylene group optionally substituted with a halogen atom, a carboxyl group, or a phenyl group. However, when both X and Y are oxygen atoms and n is 2, 2 is not an 0-phenylene group. ] [wherein x, y, z and n are the same as above]. ] A method for producing an acid imide compound represented by
基、低級シクロアルケニレン基またはアリーレン基を表
わすか、ハロゲン原子、カルボキシル基またはフェニル
基で置換されていてもよい低級アルケニレン基を表わす
。ｎは１．２．８または４を表わす。ただし、 ト−
１ｎ が２であるとき、２はＯ−フェニレン基ではない。］ で示される化合物と三硫化リンとを反応させることを特
徴とする一般式 （１ Ｅ式中、２およびｎは前記と同じである。］で示される
酸イミド系化合物の製造法。(3) General formula () [In the formula, 2 represents a lower alkylene group, a lower cycloalkylene group, a lower cycloalkenylene group, or an arylene group, or a lower alkenylene optionally substituted with a halogen atom, a carboxyl group, or a phenyl group. represents a group. n represents 1.2.8 or 4. However, to
When 1n is 2, 2 is not an O-phenylene group. ] A method for producing an acid imide compound represented by the general formula (1E, in which 2 and n are the same as above), which comprises reacting the compound represented by the above with phosphorus trisulfide.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10623383A JPS59231068A (en) | 1983-06-13 | 1983-06-13 | Acid amide compound and its preparation |
| US06/610,789 US4709052A (en) | 1983-05-31 | 1984-05-16 | Soil disease-controlling imides |
| CA000455433A CA1261839A (en) | 1983-05-31 | 1984-05-30 | 2-cycloalkenylamine derivatives |
| AU28856/84A AU576503B2 (en) | 1983-05-31 | 1984-05-30 | Soil disease controlling agents |
| KR1019840002994A KR840009289A (en) | 1983-05-31 | 1984-05-30 | Method for preparing 2-cycloalkenyl amine derivative |
| EP84303640A EP0128006B1 (en) | 1983-05-31 | 1984-05-30 | A soil-disease-controlling agent |
| DE8484303640T DE3485073D1 (en) | 1983-05-31 | 1984-05-30 | AGENTS FOR COMBATING BASIC DISEASES. |
| US07/066,735 US5075488A (en) | 1983-05-31 | 1987-06-25 | Soil disease-controlling cyano and ester derivatives of cyclopentenyl amine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10623383A JPS59231068A (en) | 1983-06-13 | 1983-06-13 | Acid amide compound and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59231068A true JPS59231068A (en) | 1984-12-25 |
| JPH042588B2 JPH042588B2 (en) | 1992-01-20 |
Family
ID=14428400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10623383A Granted JPS59231068A (en) | 1983-05-31 | 1983-06-13 | Acid amide compound and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59231068A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60156668A (en) * | 1984-01-25 | 1985-08-16 | Sumitomo Chem Co Ltd | Acid imide compound and its preparation |
| JP2006516628A (en) * | 2003-01-31 | 2006-07-06 | アストラゼネカ アクツィエボラーグ | Saturated quinoxaline derivatives and their use as metabotropic glutamate receptor ligands |
-
1983
- 1983-06-13 JP JP10623383A patent/JPS59231068A/en active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60156668A (en) * | 1984-01-25 | 1985-08-16 | Sumitomo Chem Co Ltd | Acid imide compound and its preparation |
| JPH0527621B2 (en) * | 1984-01-25 | 1993-04-21 | Sumitomo Chemical Co | |
| JP2006516628A (en) * | 2003-01-31 | 2006-07-06 | アストラゼネカ アクツィエボラーグ | Saturated quinoxaline derivatives and their use as metabotropic glutamate receptor ligands |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH042588B2 (en) | 1992-01-20 |
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