JPH03151385A - New tetracyclic condensed heterocyclic compound and herbicide - Google Patents
New tetracyclic condensed heterocyclic compound and herbicideInfo
- Publication number
- JPH03151385A JPH03151385A JP28850589A JP28850589A JPH03151385A JP H03151385 A JPH03151385 A JP H03151385A JP 28850589 A JP28850589 A JP 28850589A JP 28850589 A JP28850589 A JP 28850589A JP H03151385 A JPH03151385 A JP H03151385A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- herbicide
- lower alkyl
- heterocyclic compound
- 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.)
- Pending
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 8
- 239000004009 herbicide Substances 0.000 title claims abstract description 7
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 4
- 238000001816 cooling Methods 0.000 abstract description 2
- 239000012442 inert solvent Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract description 2
- VBPNSOZJOPBQFT-UHFFFAOYSA-N 13-methyl-16-oxa-10-azatetracyclo[8.8.0.02,7.012,17]octadeca-2,4,6,8,12(17),13-hexaene-11,15-dione Chemical compound C1=CC=C2C3CC(OC(=O)C=C4C)=C4C(=O)N3C=CC2=C1 VBPNSOZJOPBQFT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- -1 clays Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 230000002262 irrigation Effects 0.000 description 2
- 238000003973 irrigation Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000254158 Lampyridae Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 244000155437 Raphanus sativus var. niger Species 0.000 description 1
- 229920001938 Vegetable gum Polymers 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、四環系縮合複素環化合物に属する一群の新規
な化合物に関する。また、゛四環系縮合複素環化合物化
合物を有効成分として含有する除草剤に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a group of novel compounds belonging to the tetracyclic fused heterocyclic compounds. The present invention also relates to a herbicide containing a tetracyclic fused heterocyclic compound as an active ingredient.
（従来の技術）
従来、四環系縮合複素環化合物に属する化合物としては
、薬学雑誌、第８４巻、８７４頁（１９６４年）、薬学
雑誌、第８７巻、５９７頁（１９６７年）及び薬学雑誌
、第１００巻、５７１頁（１９８０年）に記載されたも
のが知られているが、本発明の化合物については従来報
告されておらず、また、四環系縮合複素環化合物が除草
活性を有することは知られてぃなかった。(Prior Art) Conventionally, as compounds belonging to tetracyclic fused heterocyclic compounds, Pharmaceutical Journal, Vol. 84, page 874 (1964), Pharmaceutical Journal, Vol. 87, page 597 (1967), and Pharmaceutical Journal , Vol. 100, p. 571 (1980), but the compound of the present invention has not been previously reported, and it is also known that the compound of the present invention has a herbicidal activity. That was not known.
本発明は、四環系縮合複素環化合物に属する一群の新規
化合物および四環系縮合複素環化合物のうち少なくとも
一種を有効成分として含有する除草剤を提供するもので
ある。The present invention provides a herbicide containing as an active ingredient at least one of a group of new compounds belonging to the fused tetracyclic fused heterocyclic compounds and the fused tetracyclic fused heterocyclic compounds.
（発明の構成）
本発明は、下記の式（Ｉ）で示される化合物が提供され
る。(Structure of the Invention) The present invention provides a compound represented by the following formula (I).
ルキル基） ； Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６及びＲ
７は同一または異なって水素原子、ハロゲン原子もしく
は低級アルキル基を示す。］
本発明の低級アルキル基とは、０１〜Ｃ６の炭素原子を
含有する基を意味する。例えば、メチル、エチル、プロ
ピル、イソプロピル、ブチル、イソブチル、ペンチル、
イソペンチル、ヘキシル、イソヘキシルなどが挙げられ
る。ハロゲン原子とは、塩素、臭素、フッ素、ヨウ素等
が挙げられる。R2, R3, R4, R5, R6 and R
7 is the same or different and represents a hydrogen atom, a halogen atom, or a lower alkyl group. ] The lower alkyl group of the present invention means a group containing 01 to C6 carbon atoms. For example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl,
Examples include isopentyl, hexyl, isohexyl, and the like. Examples of halogen atoms include chlorine, bromine, fluorine, and iodine.
本発明の式（Ｉ）で示される化合物は次の方法で製造す
ることができる。The compound represented by formula (I) of the present invention can be produced by the following method.
Ａは−Ｎ−である化合物の製造
１
［式中Ｒ１、Ｒ２、Ｒａ 、 Ｒ４、Ｒ５、Ｒ６、Ｒ７
は式（工′）の定義と同一］
この方法は、式（ＩＩ ）の化合物に無溶媒または不活
性溶媒中、式（ＩＩＩ ）で示される化合物を作用させ
ることによって行われる。反応温度は、水冷下から約１
２０°Ｃの範囲が好ましい。式（ＩＩＩ）の化合物は式
（ＩＩ ）の化合物に対して当量以上使用するのが好ま
しい。この際、トリエチルアミン、ピリジン、炭酸ナト
リウム、水酸化ナトリウムなどの有機もしくは無機の塩
基を添加すると反応が円滑に進行する。Production 1 of compounds in which A is -N- [wherein R1, R2, Ra, R4, R5, R6, R7
is the same as the definition of formula (E')] This method is carried out by reacting the compound of formula (II) with the compound of formula (III) without a solvent or in an inert solvent. The reaction temperature is approximately 1
A range of 20°C is preferred. The compound of formula (III) is preferably used in an amount equal to or more than the amount of the compound of formula (II). At this time, the reaction proceeds smoothly by adding an organic or inorganic base such as triethylamine, pyridine, sodium carbonate, or sodium hydroxide.
本発明は、式（Ｉ”）に示す化合物の少なくとも一種を
有効成分として含有する除草剤を提供するものである。The present invention provides a herbicide containing at least one compound represented by formula (I'') as an active ingredient.
本発明除草剤は、前記式（■”）て示される有効成分化
合物をそのまま使用してもよいが、一般にはその使用目
的に応じて固体担体、液体担体、界面活性剤、その他の
製剤用補助剤と混合して水利剤、粒剤、乳剤等に製剤す
る。In the herbicide of the present invention, the active ingredient compound represented by the above formula (■'') may be used as is, but in general, depending on the purpose of use, solid carriers, liquid carriers, surfactants, and other formulation auxiliaries are used. It is mixed with other agents and formulated into irrigation agents, granules, emulsions, etc.
これらの製剤には、該化合物を有効成分として、水利剤
では１０〜８０％、粒剤では１〜１０％、乳剤では１０
〜５０％（いずれも重量％を示す）を含有することが望
ましい。These preparations contain the compound as an active ingredient, 10 to 80% for aquariums, 1 to 10% for granules, and 10% for emulsions.
It is desirable that the content is 50% (all percentages are by weight).
製剤に使用される固体担体には、カオリン、ベントナイ
ト、クレー類、タルク、珪藻土、ジ−クライト、ゼオラ
イト、パイロフィライト、合成含水酸化珪素、炭酸カル
シウム等の微粉末あるいは粒状物があり、液体担体には
、キシレン、メチルナフタレン等の芳香族炭化水素類、
エタノール、イソプロパツール、エチレングリコール、
メチルセロソルブ等のアルコール類、アセトン、イソホ
ロン、シクロヘキサノン等のケトン類、大豆油、綿実油
等の植物油、ジメチルホルムアミド、ジメチルスルホオ
キシド、アセトニトリル、水等がある。Solid carriers used in formulations include fine powders or granules such as kaolin, bentonite, clays, talc, diatomaceous earth, gicrite, zeolite, pyrophyllite, synthetic hydrous silicon oxide, and calcium carbonate, and liquid carriers. Aromatic hydrocarbons such as xylene and methylnaphthalene,
Ethanol, isopropanol, ethylene glycol,
Examples include alcohols such as methyl cellosolve, ketones such as acetone, isophorone, and cyclohexanone, vegetable oils such as soybean oil and cottonseed oil, dimethylformamide, dimethyl sulfoxide, acetonitrile, and water.
乳化、分散、湿炭等のために用いられる界面活性剤には
、ポリオキシエチレンアルキルエーテル、ポリオキシエ
チレンアルキルアリールエーテル、ポリオキシエチレン
脂肪酸エステル、ソルビタン脂肪酸エステル、ポリオキ
シエチレンソルビタン脂肪酸エステル、ポリオキシエチ
レンポリオキシプロピレンプロツクポリマー等のノニオ
ン性界面活性剤、アルキル硫酸エステル塩、アルキルス
ルホン酸塩、アルキルアリールスルホン酸塩、ポリオキ
シエチレンアルキル硫酸エステル塩等のアニオン性界面
活性剤等がある。Surfactants used for emulsification, dispersion, wet carbonization, etc. include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester. Examples include nonionic surfactants such as ethylene polyoxypropylene block polymers, anionic surfactants such as alkyl sulfate salts, alkyl sulfonate salts, alkylaryl sulfonate salts, and polyoxyethylene alkyl sulfate salts.
製剤用補助剤には、リグニンスルホン酸塩、アルギン酸
塩、ポリアクリレート類、ポリビニルアルコール、植物
ガム類、カルボキシメチルセルロース（ＣＭＣ）、ヒド
ロキシエチルセルロース（ＨＥＣ）等がある。Formulation adjuvants include lignin sulfonates, alginates, polyacrylates, polyvinyl alcohol, vegetable gums, carboxymethyl cellulose (CMC), hydroxyethyl cellulose (HEC), and the like.
（実施例）
次に、本発明を実施例によって説明する。なお、実施例
に示した化合物の他に、本発明に含まれる興味ある化合
物としては、次のものが挙げられる。（表１）
（合成例）
合成例１
１３．１３ａ−ジヒドロ−９−メチル−８Ｈ−イソキノ
Ｌ２，１ｇ１［１，６］ナフチリジン−８，１１（１２
Ｈ）−ジオン（化合老歯１）の製造。(Example) Next, the present invention will be explained by referring to an example. In addition to the compounds shown in the examples, the following compounds may be included as interesting compounds included in the present invention. (Table 1) (Synthesis Example) Synthesis Example 1 13.13a-dihydro-9-methyl-8H-isoquino L2,1g1[1,6]naphthyridine-8,11(12
Production of H)-dione (compound old tooth 1).
１３．１３ａ−ジヒドロ−９−メチル−８Ｈ，ＩＩＨ−
ベンゾ［ａ］ヒラノ［３，２−ｇ］キノリジン−８，１
１−ジオン（化合物Ｎｃｔ２）１．５０ｇ 、濃アンモ
ニア水０．５７ｍ１及び水４０ｍＩＣ混合物を５０°Ｃ
で４時間撹はんした。反応混合物を冷却した後、析出し
た結晶をシリカゲルカラムクロマトグラフィーによって
処理し、連記化合物を０．１１ａ得た。13.13a-dihydro-9-methyl-8H,IIH-
Benzo[a]hylano[3,2-g]quinolidine-8,1
A mixture of 1.50 g of 1-dione (compound Nct2), 0.57 ml of concentrated ammonia water, and 40 m of water was heated at 50°C.
The mixture was stirred for 4 hours. After cooling the reaction mixture, the precipitated crystals were treated with silica gel column chromatography to obtain 0.11a of the above mentioned compound.
融点 １７８．５〜１８５．５°Ｃ
ＩＲ（ＫＢｒディスク）： ７８２ 、１２５０ 、１
４６５ 、１５９７１６４０ｃｍ’
ＮＭＲ（ＣＤ０１ａ）δ値：
２．４８（ｓ 、 ３Ｈ） 、 ３．００−４．１０（
ｍ 、 ２Ｈ） 、 ５．２５（ｑ 、 ＩＨ） 。Melting point 178.5-185.5°C IR (KBr disk): 782, 1250, 1
465, 15971640 cm' NMR (CD01a) δ value: 2.48 (s, 3H), 3.00-4.10 (
m, 2H), 5.25(q, IH).
５．９５（ｄ 、 ＬＨ） 、 ６．６０（ｓ 、 Ｉ
Ｈ） 、 ６．８０−７．５０（ｍ 、 ５Ｈ） 。5.95 (d, LH), 6.60 (s, I
H), 6.80-7.50 (m, 5H).
１２．６５（ｂｒ 、 ＩＨ）
なお、化合物Ｎα２は薬学雑誌、１００．５７１（１９
８０）記載の方法に従って合成した。12.65 (br, IH) Compound Nα2 is published in Pharmaceutical Journal, 100.571 (19
Synthesized according to the method described in 80).
（試験例）
植物生理活性試験
タルク（５０重量部）、ベントナイト（２５重量部）、
ツルポール−９０４７（東邦化学製、２重量部）、ソル
ボ−ルー５０３９（同前、３重量部）を混合しキャリア
ーを調製した。試験化合物にそれぞれ５０重量部と前記
キャリアー２００重量部とを混合し、２０％永和剤を作
った。この水和剤を純水に分散させ所定濃度の水和剤分
散液を得た。別にイネ、ノビエ、二十日ダイコン、ホタ
ルイ種子を催芽させたシャーレを用意し、上記水利剤分
赦液を添加し、２５°Ｃの照明付き定温庫で７日間育苗
して成長程度を以下の基準に従って評価し、その結果を
表２に示す。(Test example) Plant physiological activity test Talc (50 parts by weight), bentonite (25 parts by weight),
A carrier was prepared by mixing Trupol-9047 (manufactured by Toho Chemical Co., Ltd., 2 parts by weight) and Sorbo-Rue 5039 (manufactured by Toho Chemical Co., Ltd., 3 parts by weight). 50 parts by weight of each of the test compounds and 200 parts by weight of the carrier were mixed to prepare a 20% permanent agent. This hydrating powder was dispersed in pure water to obtain a hydrating powder dispersion having a predetermined concentration. Separately, prepare a petri dish in which seeds of rice, Japanese wildflower, Japanese daikon radish, and firefly seeds have been germinated, add the above-mentioned irrigation agent, and grow the seedlings for 7 days in a constant temperature warehouse with lighting at 25°C. It was evaluated according to the standards, and the results are shown in Table 2.
Claims (2)
１は水素原子あるいは低級アルキル基）；Ｒ＿２、Ｒ＿
３、Ｒ＿４、Ｒ＿５、Ｒ＿６及びＲ＿７は同一または異
なって水素原子、ハロゲン原子もしくは低級アルキル基
を示す。］で表される新規な四環系縮合複素環化合物。(1) Formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, A is ▲There are mathematical formulas, chemical formulas, tables, etc.▼(R_
1 is a hydrogen atom or a lower alkyl group); R_2, R_
3, R_4, R_5, R_6 and R_7 are the same or different and represent a hydrogen atom, a halogen atom or a lower alkyl group. ] A novel tetracyclic fused heterocyclic compound.
あります▼（Ｒ＿１は水素原子あるいは低級アルキル基
）；Ｒ＿２、Ｒ＿３、Ｒ＿４、Ｒ＿５、Ｒ＿６及びＲ＿
７は同一または異なって水素原子、ハロゲン原子もしく
は低級アルキル基を示す。］で表される四環系縮合複素
環化合物の少なくとも一種を有効成分として含有するこ
とを特徴とする除草剤。(2) Formula (I'): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, A is an oxygen atom or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (R_1 is a hydrogen atom or a lower alkyl group); R_2 , R_3, R_4, R_5, R_6 and R_
7 is the same or different and represents a hydrogen atom, a halogen atom, or a lower alkyl group. ] A herbicide characterized by containing at least one type of tetracyclic fused heterocyclic compound represented by the following as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28850589A JPH03151385A (en) | 1989-11-06 | 1989-11-06 | New tetracyclic condensed heterocyclic compound and herbicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28850589A JPH03151385A (en) | 1989-11-06 | 1989-11-06 | New tetracyclic condensed heterocyclic compound and herbicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03151385A true JPH03151385A (en) | 1991-06-27 |
Family
ID=17731093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28850589A Pending JPH03151385A (en) | 1989-11-06 | 1989-11-06 | New tetracyclic condensed heterocyclic compound and herbicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03151385A (en) |
-
1989
- 1989-11-06 JP JP28850589A patent/JPH03151385A/en active Pending
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