JPH085765B2 - Herbicide containing benzoyloxamide derivative - Google Patents
Herbicide containing benzoyloxamide derivativeInfo
- Publication number
- JPH085765B2 JPH085765B2 JP4747587A JP4747587A JPH085765B2 JP H085765 B2 JPH085765 B2 JP H085765B2 JP 4747587 A JP4747587 A JP 4747587A JP 4747587 A JP4747587 A JP 4747587A JP H085765 B2 JPH085765 B2 JP H085765B2
- Authority
- JP
- Japan
- Prior art keywords
- benzoyloxamide
- derivative
- parts
- compound
- herbicide containing
- 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 - Lifetime
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 20
- 239000004009 herbicide Substances 0.000 title claims description 10
- KNJDRGUFIWQJHI-UHFFFAOYSA-N n'-benzoyloxamide Chemical class NC(=O)C(=O)NC(=O)C1=CC=CC=C1 KNJDRGUFIWQJHI-UHFFFAOYSA-N 0.000 title claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 7
- 241000196324 Embryophyta Species 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000002689 soil Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000008187 granular material Substances 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- -1 benzoyloxamide 1- (2-methylphenyl) hydrazone Compound Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- QKCKCXFWENOGER-UHFFFAOYSA-N 2-phenyloxazol-5(4H)-one Chemical compound O1C(=O)CN=C1C1=CC=CC=C1 QKCKCXFWENOGER-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、ベンゾイルオキサミド誘導体を有効成分と
して利用する除草剤に関する。TECHNICAL FIELD The present invention relates to a herbicide which uses a benzoyloxamide derivative as an active ingredient.
技術的背景 下記一般式（Ｉ）で示されるベンゾイルオキサミド誘
導体は公知の化合物であつて、その合成法も「ジヤーナ
ル オブ ザ ケミカル ソサエテイ（Journal of the
Chemical Society）vol.1962,575,（1962）」に記載さ
れている。Technical Background The benzoyloxamide derivative represented by the following general formula (I) is a known compound, and its synthesis method is also described in “Journal of the Chemical Society”.
Chemical Society) vol.1962,575, (1962) ".
（式中、CH3基はオルト位又はメタ位を表わす） しかし、これらの化合物の整理活性作用についての記
載はみられず、勿論除草作用についての報告も未だみら
れない。 (In the formula, the CH 3 group represents an ortho position or a meta position) However, there is no description of the organizing activity of these compounds, and, of course, no report of the herbicidal action is found.
発明が解決しようとする課題 近年、有用作物と雑草に同時に適用しても、作物に対
して害を与えずに雑草のみを枯殺する、選択的作用を有
する除草剤が強く要望されている。Problems to be Solved by the Invention In recent years, there has been a strong demand for a herbicide having a selective action that kills only weeds without damaging the crops even when applied to useful crops and weeds at the same time.
本発明は、このような状況に鑑みなされたものであつ
て、イネ科植物及び広葉植物、特に広葉植物に対して優
れた除草性を示し、一方、イネ、コムギ、トウモロコシ
等の作物に対して薬害を示さない除草剤を提供すること
を課題とする。The present invention has been made in view of such a situation, and shows excellent herbicidal activity against grasses and broad-leaved plants, especially broad-leaved plants, while rice, wheat, and crops such as corn. It is an object to provide a herbicide that does not show phytotoxicity.
以下本発明を詳しく説明する。 The present invention will be described in detail below.
発明の構成 本発明に係る除草剤の特徴は、下記一般式（Ｉ）で示
されるベンゾイルオキサミド誘導体を有効成分とするこ
とにある。Composition of the Invention The feature of the herbicide according to the present invention is to use a benzoyloxamide derivative represented by the following general formula (I) as an active ingredient.
（式中、CH3基はオルト位又はメタ位を表わす） 課題を解決するための手段 本発明有効成分として用いる上記一般式（Ｉ）で示さ
れるベンゾイルオキサミド誘導体は下記化合物を包含す
る。 (In the formula, CH 3 group represents an ortho position or a meta position) Means for Solving the Problems The benzoyloxamide derivative represented by the above general formula (I) used as the active ingredient of the present invention includes the following compounds.
化合物No.1 ベンゾイルオキサミド１−（２−メチルフ
エニル）ヒドラゾン 化合物No.2 ベンゾオキサミド１−（３−メチルフエニ
ル）ヒドラゾン これらの化合物は、前掲の文献に記載された方法に従
つて容易に合成することができる。Compound No. 1 benzoyloxamide 1- (2-methylphenyl) hydrazone Compound No. 2 benzoxamide 1- (3-methylphenyl) hydrazone These compounds can be easily synthesized according to the method described in the above-mentioned document. it can.
すなわち、下記反応式１に示されるように、まず、一
般式（II）で示されるアニリン誘導体に亜硝酸を作用さ
せて、一般式（III）のジアゾニウム塩を得、このジア
ゾニウム塩に式（IV）の２−フエニル−２−オキサゾリ
ン−５−オンを反応させて一般式（Ｖ）で示されるヒド
ラゾノオキサゾリン誘導体を得る。That is, as shown in the following reaction formula 1, first, a nitrous acid is allowed to act on an aniline derivative represented by the general formula (II) to obtain a diazonium salt of the general formula (III). 2) 2-phenyl-2-oxazoline-5-one is reacted to obtain a hydrazonooxazoline derivative represented by the general formula (V).
次いで、このヒドラゾノオキサゾリン誘導体にアムモ
ニアを作用させると、一般式（Ｉ）で示されるベンゾイ
ルオキサミドフエニルヒドラゾン誘導体が高収率で得ら
れる。Next, when Ammonia is allowed to act on this hydrazonooxazoline derivative, the benzoyloxamidophenylhydrazone derivative represented by the general formula (I) is obtained in high yield.
上述のようにして合成して得られるベンゾイルオキサ
ミドフエニルヒドラゾン誘導体を除草剤成分として利用
するには、一般に農業用薬剤の調製に用いられる広範囲
の種類の担体（希釈剤）及び助剤等を使用して、水和
剤、乳剤、粒剤、粉剤等の形態に調製するとよい。 In order to utilize the benzoyloxamidophenylhydrazone derivative obtained by synthesis as described above as a herbicide component, a wide variety of carriers (diluents) and auxiliaries generally used for the preparation of agricultural chemicals are used. It may be used to prepare wettable powder, emulsion, granule, powder and the like.
上記ベンゾイルオキサミドフエニルヒドラゾン誘導体
である前記化合物No.1並びに化合物No.2を有効成分とす
る除草剤は、広範囲の種類に雑草に対して優れた枯殺効
果を示し、一方、イネ、コムギ、トウモロコシ等の作物
に対しては実質上薬害を起さないので、実用性が高い。The herbicides containing the compound No. 1 and the compound No. 2 which are the benzoyloxamidophenylhydrazone derivatives as active ingredients show an excellent killing effect against weeds in a wide variety of species, while rice and wheat. Since it does not cause chemical damage to crops such as corn and corn, it is highly practical.
実施例と効果 以下に実施例を示して、本発明に係る除草剤の調製と
その除草効果を具体的に説明する。各実施例中の部は特
記しない限り重量を表わす。EXAMPLES AND EFFECTS The preparation of the herbicide according to the present invention and the herbicidal effect thereof will be specifically described below with reference to Examples. Parts in the examples represent weight unless otherwise specified.
実施例１ 水和剤の調製： 化合物No.1 50部 リグニンスルホン酸塩 ５部 アルキルスルホン酸塩 ３部 珪藻土 42部 を混合粉砕し水和剤として水で希釈して使用する。Example 1 Preparation of wettable powder: Compound No. 1 50 parts Lignin sulfonate 5 parts Alkyl sulfonate 3 parts Diatomaceous earth 42 parts are mixed and ground and used as a wettable powder diluted with water.
実施例２ 乳剤の調製： 化合物No.2 25部 キシレン 65部 ポリオキシエチレンアルキルアリルエーテル 10部 を均一に混合し乳剤とし水で希釈して使用する 実施例３ 粒剤の調製： 化合物No.2 ８部 ベントナイト 40部 クレー 45部 リグニンスルホン酸塩 ７部 を均一に混合し更に水を加え練り合わせ押出式造粒機で
粒状に加工乾燥して粒剤とする。Example 2 Preparation of emulsion: 25 parts of compound No. 2 65 parts of xylene 10 parts of polyoxyethylene alkylallyl ether are uniformly mixed and used as an emulsion and diluted with water. Example 3 Preparation of granules: compound No. 2 8 parts Bentonite 40 parts Clay 45 parts Lignin sulfonate 7 parts Uniformly mixed, further mixed with water, kneaded, and processed into granules by an extrusion granulator and dried to give granules.
なお、実施例１〜３に示された担体（希釈剤）及び助
剤、その混合比は広い範囲で変更し得る。The carriers (diluents) and auxiliaries shown in Examples 1 to 3 and the mixing ratio thereof can be changed within a wide range.
次に、本発明に係る除草剤の除草効果を試験した結果
を例示する。Next, the results of testing the herbicidal effect of the herbicide according to the present invention will be exemplified.
試験例１ 畑地雑草に対する除草効果（発芽前土壌処理） プランター（650×210×220mm）に砂壌土を充填して
畑地状となしたものに、種々の植物種子の一定量を播種
し、覆土した後、実施例１に従つて調製した、化合物N
o.1並びに化合物No.2をそれぞれ有効成分とする水和剤
を所定濃度に水で希釈してスプレーガンにより、減退成
分が200g/10アールとなる量を土壌表面に均一に散布
し、その後ガラス温室内で育成管理した。Test Example 1 Herbicidal effect against field weeds (pre-emergence soil treatment) A planter (650 x 210 x 220 mm) was filled with sandy loam soil to form a field, and a certain amount of various plant seeds were sown and covered with soil. Then, the compound N prepared according to Example 1
o.1 and the compound No. 2 as the active ingredient are each diluted with water to a predetermined concentration and spray gun is used to spray 200 g / 10 ares of the reduced component evenly over the soil surface. It was grown and managed in a glass greenhouse.
上記処理から21日目に各雑草に対する殺草効果及び作
物に対する薬剤を観察し、下記の基準により評価を行つ
た。結果は表１に示すとおりである。On the 21st day after the above treatment, the herbicidal effect against each weed and the drug against the crops were observed, and evaluated according to the following criteria. The results are shown in Table 1.
評価基準;0……効果なし 1……30％未満の殺草効果 2……31〜50％の殺草効果 3……51〜70％の殺草効果 4……71〜91％の殺草効果 5……91〜100％の殺草効果 試験例２ 畑地雑草に対する効果（発芽後土壌処理） 試験例１に記載したと同様の手段に従つて、種々の植
物の種子を播種し、各植物が１〜２葉期に達した時期に
試験例１と同様に水で希釈した水和剤を原体成分で200g
/10アールとなる量をスプレーガンにより各植物の茎葉
部と土壌表面に均一に散布した後、再びガラス温室内に
て育成管理し、処理後21日後に試験例１に示したと同様
な基準にて評価した。Evaluation criteria; 0 …… No effect 1 …… Less than 30% herbicidal effect 2 …… 31 ～ 50% herbicidal effect 3 …… 51 ～ 70% herbicidal effect 4 …… 71 ～ 91% herbicidal effect Effect 5 …… 91 ~ 100% herbicidal effect Test Example 2 Effect on upland weeds (post-emergence soil treatment) According to the same procedure as described in Test Example 1, seeds of various plants were sown, and each plant was tested at the time when it reached 1-2 leaf stage. 200g of the active ingredient diluted with water in the same manner as in Example 1
After spraying evenly the amount of / 10 are on the foliage of each plant and the soil surface with a spray gun, it was again grown and managed in a glass greenhouse, and 21 days after the treatment, the same criteria as shown in Test Example 1 were applied. Evaluated.
結果は表２に示すとおりである。 The results are shown in Table 2.
Claims (1)
れるベンゾイルオキサミド誘導体を有効成分とする除草
剤。1. A general formula A herbicide containing a benzoyloxamide derivative represented by the formula (CH 3 group represents an ortho position or a meta position) as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4747587A JPH085765B2 (en) | 1987-03-04 | 1987-03-04 | Herbicide containing benzoyloxamide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4747587A JPH085765B2 (en) | 1987-03-04 | 1987-03-04 | Herbicide containing benzoyloxamide derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63215604A JPS63215604A (en) | 1988-09-08 |
| JPH085765B2 true JPH085765B2 (en) | 1996-01-24 |
Family
ID=12776165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4747587A Expired - Lifetime JPH085765B2 (en) | 1987-03-04 | 1987-03-04 | Herbicide containing benzoyloxamide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH085765B2 (en) |
-
1987
- 1987-03-04 JP JP4747587A patent/JPH085765B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63215604A (en) | 1988-09-08 |
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