JPH0363522B2 - - Google Patents
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- Publication number
- JPH0363522B2 JPH0363522B2 JP23044182A JP23044182A JPH0363522B2 JP H0363522 B2 JPH0363522 B2 JP H0363522B2 JP 23044182 A JP23044182 A JP 23044182A JP 23044182 A JP23044182 A JP 23044182A JP H0363522 B2 JPH0363522 B2 JP H0363522B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- compound
- compounds
- soil
- test
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 23
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- 239000004009 herbicide Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 9
- 239000002689 soil Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
- 235000009566 rice Nutrition 0.000 description 6
- 244000025254 Cannabis sativa Species 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000234653 Cyperus Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000234609 Portulaca oleracea Species 0.000 description 3
- 235000001855 Portulaca oleracea Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000009333 weeding Methods 0.000 description 3
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical group OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical group C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- TYJMXMFZUFPWIK-UHFFFAOYSA-N 2-methylpyridazin-3-one Chemical compound CN1N=CC=CC1=O TYJMXMFZUFPWIK-UHFFFAOYSA-N 0.000 description 1
- SUNABRFQDJGDSE-UHFFFAOYSA-N 6-methyl-3-phenylpyridazino[4,5-e][1,2,4]triazin-5-one Chemical compound N1=C2C(=O)N(C)N=CC2=NN=C1C1=CC=CC=C1 SUNABRFQDJGDSE-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- 239000005493 Chloridazon (aka pyrazone) Substances 0.000 description 1
- 244000301850 Cupressus sempervirens Species 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 241001517923 Douglasiidae Species 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000005583 Metribuzin Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 241000251778 Squalus acanthias Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
本発明は一般式（）：
〔但し、式中Ｒは直鎖の低級アルキル基を表
す。
で表わされる化合物（以下単に本発明化合物とい
う）の１種又は２種以上を有効成分とすることを
特徴とする選択性除草剤に関するものである。
従来、３（2H）−ピリダジノン環を有する選択
性除草剤として構造式（）で表わされるピラゾ
ン，構造式（）で表わされるノルフルラゾンが
知られている。一方、１，２，４−トリアジン環
を有する除草剤として例えば構造式（）で表わ
されるメトリブジンが実用化に供されている。し
かし、３（2H）−ピリダジノン環と１，２，４−
トリアジン環が縮合した本発明化合物の除草活性
については文献に記載されていない。
本発明化合物は後記の試験例に示すように土壌
処理，茎葉処理により種々の雑草に対して除草活
性を有するとともに、トウモロコシ，コムギ，オ
オムギ，ダイズ等の主要作物に顕著な選択性を有
するで除草剤として優れた特性を有するものであ
る。
本発明に包含される化合物を具体的に例示すれ
ば第１表に示す化合物を挙げることができる。但
し、第１表に示す化合物は例示のためのもので本
発明の範囲を限定するものではない。なお、化合
物番号は以下の記載においても使用するものとす
る。
The present invention is based on the general formula (): [However, in the formula, R represents a linear lower alkyl group. The present invention relates to a selective herbicide characterized by containing as an active ingredient one or more of the compounds represented by (hereinafter simply referred to as compounds of the present invention). Conventionally, pyrazone represented by the structural formula () and norflurazone represented by the structural formula () have been known as selective herbicides having a 3(2H)-pyridazinone ring. On the other hand, as a herbicide having a 1,2,4-triazine ring, for example, metribuzin represented by the structural formula () has been put into practical use. However, the 3(2H)-pyridazinone ring and the 1,2,4-
The herbicidal activity of the compounds of the present invention having fused triazine rings is not described in the literature. As shown in the test examples below, the compound of the present invention has herbicidal activity against various weeds when treated with soil and foliage, and has remarkable selectivity for weeding major crops such as corn, wheat, barley, and soybean. It has excellent properties as a drug. Specific examples of compounds included in the present invention include those shown in Table 1. However, the compounds shown in Table 1 are for illustrative purposes only and are not intended to limit the scope of the present invention. In addition, the compound number shall also be used in the following description.
【表】【table】
【表】
本発明化合物の合成法は一部第11回複素環化学
討論会（1978年）で発表されている（講演要旨集
383頁）。しかし、本発明者らはその後合成法を改
良し、次に示す方法で本発明化合物を合成した。
反応式(1)及び(2)を経て合成した化合物（）を
メタノール性アンモニアと封管中で加熱して閉環
及び脱水素反応を同時に行い、目的とする化合物
（）を良好な収率で得ることができる。
次に実施例により、本発明化合物の合成法を具
体的に説明する。但し、これのみに限定されるも
のではない。
実施例 １
６−メチル−３−フエニル−ピリダジノ〔4.5
−ｅ〕−as−トリアジン−５（6H）オン（化合
物No.１）の合成
０℃でアンモニアガスを飽和させたメタノール
50mlと５−ベンゾイルヒドラジノ−４−クロル−
２−メチル−３（2H）ピリダジノン2.8ｇを耐圧
密封容器中、120℃の油浴中で５時間加熱した。
放冷後容器を開封し、内容物を減圧下で乾固し
た。残渣をエタノールから再結晶してmp212〜
214℃の目的物1.8ｇを得た。
本発明化合物を有効成分とする除草剤を実際に
使用する際には、該化合物の１種又は２種以上を
公知の処方に従つて、不活性な適当な担体と組合
せ、液剤，水和剤，乳剤，粉剤，粒剤などの使い
易い形態に調製するのが適当である。この場合に
用いられる担体は固体担体としては例えばクレ
ー，タルク，ベントナイト，ケイソウ土などが挙
がられる。
また液体担体としては、例えば水，アルコール
類，アセトン，ベンゼン，キシレン，Ｎ，Ｎ−ジ
メチルホルムアミド等が挙げられる。
製剤上の補助剤として乳化剤，分散剤，浸透剤
等の界面活性剤を適宜使用し得る。
なお、本発明化合物は畑地，水田，果樹園など
の農園芸分野以外に運動場，空地，線路端など非
農耕地における各種雑草の防除にも適用すること
ができ、その施用薬量は適用場面，施用時期，施
用方法，対象草種，栽培作物等により差異はある
が、一般には有効成分量として10アール当り５〜
1000ｇ程度が適当である。
次に本発明化合物を有効成分とする除草剤の配
合例を具体的に挙げて説明する。但し、これらの
配合例のみに限定されるものではない。
なお、以下の「部」は重量部を意味するもので
ある。
配合例１ 乳剤
〓本発明化合物 50部
Ｎ，Ｎ−ジメチルホルムアミド 45部
ソルボール2175（乳化剤，東邦化学製） ５部
以上を均一に混和溶解して乳剤とする。使用に
際しては、水で希釈して散布する。
配合例２ 水和剤
〓本発明化合物 25部
ジークライトＡ（商品名） 69部
ソルボールBC8048（界面活性剤，東邦化学製）
３部
カーブレツクス（固結防止剤，塩野義製薬製）
３部
以上を均一に混合粉砕して水和剤とする。使用
に際しては、水で希釈して散布する。
次に本発明化合物の除草効果及び作物選択性に
ついて試験例により説明する。
試験例１ 土壌処理による除草効果試験
縦15cm，横22cm，深さ６cmのプラスチツク製箱
に殺菌した洪積土壌を入れ、イネ，メヒシバ，カ
ヤツリグサ，コアカザ，スベリヒユ，イヌガラ
シ，ハキダメギクを混種し、約1.5cm覆土した後、
本発明化合物が25ｇ／ａの割合となるよう土壌表
面に散布した。散布の際の薬液は前記配合例２の
水和剤を水で希釈して小型スプレーで散布した。
薬液散布３週間後にイネおよび各雑草に対する除
草効果を下記判定基準に従い調査した。結果を第
２表に示す。
判定基準
５ 殺草率90％以上
４ 〃70〜90％
３ 〃40〜70％
２ 〃20〜40％
１ 〃５〜20％
０ 〃５％以下
但し、上記の殺草率は、薬剤処理の地上部生草
重および無処理区の地上部生草重を測定して下記
の式により求めたものである。
殺草率（％）＝（１−処理区の地上部生草重／無処理区
の地上部生草重）×
100
試験例２ 茎葉処理による除草効果試験
縦15cm，横22cm，深さ６cmのプラスチツク製箱
に殺菌した洪積土壌を入れ、イネ，メヒシバ，カ
ヤツリグサ，コアカザ，スベリヒユ，イヌガラ
シ，ハキダメギタの種子をそれぞれスポツト状に
播種し、約1.5cm覆土した。イネ及び各種雑草が
２〜３葉期に達したとき、本発明化合物が25ｇ／
ａの割合になるように茎葉部へ散布した。散布の
際の薬液は前記配合例２の水和剤を水で希釈し小
型スプレーでイネ及び各種雑草の茎葉部の全面に
散布した。
薬液散布２週間後，イネ及び各種雑草に対する
防除効果を試験例１に記載した判定基準に従つて
調査した。結果を第２表に示す。[Table] Some of the methods for synthesizing the compounds of the present invention were presented at the 11th Heterocyclic Chemistry Symposium (1978) (collection of lecture abstracts).
383 pages). However, the present inventors subsequently improved the synthesis method and synthesized the compound of the present invention by the method shown below. Compound () synthesized through reaction formulas (1) and (2) is heated with methanolic ammonia in a sealed tube to simultaneously perform ring-closing and dehydrogenation reactions to obtain the target compound () in good yield. be able to. Next, the method for synthesizing the compounds of the present invention will be specifically explained with reference to Examples. However, it is not limited to this only. Example 1 6-methyl-3-phenyl-pyridazino [4.5
-e]-as-triazin-5(6H)one (compound No. 1) synthesis Methanol saturated with ammonia gas at 0℃
50ml and 5-benzoylhydrazino-4-chloro-
2.8 g of 2-methyl-3(2H)pyridazinone was heated in a pressure-tight sealed container in an oil bath at 120°C for 5 hours.
After cooling, the container was opened and the contents were dried under reduced pressure. Recrystallize the residue from ethanol to obtain mp212~
1.8 g of the target product was obtained at 214°C. When actually using a herbicide containing a compound of the present invention as an active ingredient, one or more of the compounds are combined with an appropriate inert carrier according to a known formulation, and a solution or wettable powder is prepared. It is appropriate to prepare it in an easy-to-use form such as emulsion, powder, or granule. Solid carriers used in this case include, for example, clay, talc, bentonite, diatomaceous earth, and the like. Examples of liquid carriers include water, alcohols, acetone, benzene, xylene, N,N-dimethylformamide, and the like. Surfactants such as emulsifiers, dispersants, and penetrants may be used as appropriate formulation aids. The compound of the present invention can be applied to control various weeds in agricultural and horticultural areas such as fields, paddy fields, and orchards, as well as in non-agricultural areas such as playgrounds, vacant lots, and railway edges, and the amount of application depends on the application situation. There are differences depending on the application time, application method, target grass species, cultivated crops, etc., but in general, the amount of active ingredients is 5 to 5 per 10 ares.
Approximately 1000g is appropriate. Next, specific formulation examples of herbicides containing the compound of the present invention as an active ingredient will be explained. However, the composition is not limited to these examples. Note that "parts" below mean parts by weight. Formulation Example 1 Emulsion: 50 parts of the compound of the present invention, 45 parts of N,N-dimethylformamide, 5 parts of Sorbol 2175 (emulsifier, manufactured by Toho Chemical Co., Ltd.) The above ingredients are uniformly mixed and dissolved to form an emulsion. When using, dilute with water and spray. Formulation Example 2 Wettable powder: Compound of the present invention 25 parts Siegrite A (trade name) 69 parts Sorbol BC8048 (surfactant, manufactured by Toho Chemical Co., Ltd.)
3-part curvex (anti-caking agent, manufactured by Shionogi & Co., Ltd.)
Mix and grind 3 or more parts uniformly to make a wettable powder. When using, dilute with water and spray. Next, the herbicidal effects and crop selectivity of the compounds of the present invention will be explained using test examples. Test Example 1 Weeding effect test by soil treatment Sterilized diluvial soil was placed in a plastic box measuring 15 cm in length, 22 cm in width, and 6 cm in depth, and a mixture of rice, seaweed, Japanese cyperus, koakaza, purslane, dogfish, and leafminer was mixed. After covering with 1.5cm of soil,
The compound of the present invention was sprayed on the soil surface at a rate of 25 g/a. The chemical solution used for spraying was the wettable powder of Formulation Example 2 diluted with water and sprayed using a small sprayer.
Three weeks after spraying the chemical solution, the herbicidal effect on rice and each weed was investigated according to the following criteria. The results are shown in Table 2. Judgment Criteria 5 Weed killing rate 90% or more 4 70-90% 3 40-70% 2 20-40% 1 5-20% 0 5% or less However, the above weed killing rate is for the above-ground part of chemical treatment. It was calculated by measuring the fresh grass weight and the above-ground fresh grass weight in the untreated area using the following formula. Weed killing rate (%) = (1 - Weight of above-ground grass in treated area / Weight of above-ground grass in non-treated area) x 100 Test example 2 Weeding effect test by foliage treatment Plastic 15 cm long, 22 cm wide, 6 cm deep Sterilized diluvial soil was placed in a box, and the seeds of rice, crabgrass, cyperus, cyperus, purslane, purslane, and cypress were sown in spots and covered with soil to a depth of approximately 1.5 cm. When rice and various weeds reach the 2-3 leaf stage, the compound of the present invention is added at 25g/
It was sprayed on the stems and leaves at a ratio of a. The chemical solution for spraying was the hydrating powder of Formulation Example 2 diluted with water and sprayed over the entire surface of the stems and leaves of rice and various weeds using a small sprayer. Two weeks after spraying the chemical solution, the control effect on rice and various weeds was investigated according to the criteria described in Test Example 1. The results are shown in Table 2.
【表】
試験例３ 作物に対する選択性試験
縦15cm，横22cm，深さ６cmのプラスチツク製箱
に殺菌した洪積土壌を入れ、トウモロコシ，コム
ギ，オオムギ，ソルガム，ダイズの種子を播種
し、試験例２と全く同様に試験を行つた。結果を
第３表に示す。[Table] Test Example 3 Selectivity test for crops Sterilized diluvial soil was placed in a plastic box measuring 15 cm long, 22 cm wide, and 6 cm deep, and seeds of corn, wheat, barley, sorghum, and soybean were sown. The test was conducted in exactly the same manner as in Example 2. The results are shown in Table 3.
Claims (1)
す。〕 で表される化合物の１種又は２種以上を有効成分
とする選択性除草剤。[Claims] 1 General formula (): [However, in the formula, R represents a linear lower alkyl group. ] A selective herbicide containing one or more of the compounds represented by as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23044182A JPS59116201A (en) | 1982-12-24 | 1982-12-24 | Selective herbicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23044182A JPS59116201A (en) | 1982-12-24 | 1982-12-24 | Selective herbicide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59116201A JPS59116201A (en) | 1984-07-05 |
| JPH0363522B2 true JPH0363522B2 (en) | 1991-10-01 |
Family
ID=16907945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23044182A Granted JPS59116201A (en) | 1982-12-24 | 1982-12-24 | Selective herbicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59116201A (en) |
-
1982
- 1982-12-24 JP JP23044182A patent/JPS59116201A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59116201A (en) | 1984-07-05 |
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