JPH03151386A - New tetracyclic condensed heterocyclic compound and herbicide - Google Patents
New tetracyclic condensed heterocyclic compound and herbicideInfo
- Publication number
- JPH03151386A JPH03151386A JP28850689A JP28850689A JPH03151386A JP H03151386 A JPH03151386 A JP H03151386A JP 28850689 A JP28850689 A JP 28850689A JP 28850689 A JP28850689 A JP 28850689A JP H03151386 A JPH03151386 A JP H03151386A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- lower alkyl
- compound
- alkyl group
- hydrogen atom
- 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 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 6
- 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 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 6
- 238000001816 cooling Methods 0.000 abstract description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 3
- 239000012442 inert solvent Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- VQKKTHJCRVBMDM-UHFFFAOYSA-N 15-methyl-16-oxa-10-azatetracyclo[8.8.0.02,7.012,17]octadeca-2,4,6,8,12(17),14-hexaene-11,13-dione Chemical compound C1=CC2=CC=CC=C2C2N1C(=O)C(C(=O)C=C(O1)C)=C1C2 VQKKTHJCRVBMDM-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 ring compounds Chemical class 0.000 description 15
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000013078 crystal 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
- 239000011541 reaction mixture Substances 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000000887 hydrating effect Effects 0.000 description 3
- 238000000034 method Methods 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
- 101150041968 CDC13 gene Proteins 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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-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
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000004094 surface-active agent Substances 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
- YYFLDZZDOUDZQM-UHFFFAOYSA-N 3-[1-[[4-(3-phenylquinolin-2-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 YYFLDZZDOUDZQM-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
- 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
- 235000005733 Raphanus sativus var niger Nutrition 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 240000001970 Raphanus sativus var. sativus 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
- 239000003945 anionic surfactant Substances 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000007864 aqueous solution 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
- 229940126214 compound 3 Drugs 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil 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
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 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
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate 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)、第
87巻、597頁(1967年)及び薬学雑誌、第10
0巻、571頁(1980年)に記載されたものが知ら
れているが、本発明の請求項(1)記載の化合物につい
ては従来報告されておらず、また、既知の四環系縮合複
素環化合物も含めて、これらの化合物が除草活性を有す
ることは知られていなかった。(Prior Art) Conventionally, compounds belonging to tetracyclic fused heterocyclic compounds have been described in Pharmaceutical Journal, Vol. 84, p. 874 (1964-), Vol. 87, p. 597 (1967) and Pharmaceutical Journal, Vol. 10
The compound described in Vol. It was not known that these compounds, including ring compounds, have herbicidal activity.
本発明は、四環系縮合複素環化合物に属する一群の新規
化合物及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 novel 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は水素原子あるいは低級アルキル基;
R3、R4、R5及び狗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:m及びnは
Oもしくは1を示す。ただし、mもしくはnは同時にO
もしくは1になることはなく、またR1及びR2が水素
原子でnが1の場合、R3、R4、R5及び狗のすべて
が同時になることない。]
ここで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
ンペンチル、ヘキシル、イソヘキシルなどが含まれる。R2 is a hydrogen atom or a lower alkyl group;
R3, R4, R5 and dog are the same or different and represent a hydrogen atom, a halogen atom or a lower alkyl group; m and n represent O or 1; However, m or n is O at the same time.
Or, if R1 and R2 are hydrogen atoms and n is 1, then R3, R4, R5 and dog cannot all be the same at the same time. ] Here, the lower alkyl group means a group containing 01 to C6 carbon atoms. Examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, impentyl, hexyl, isohexyl, and the like.
ハロゲン原子には、塩素、臭素、フッ素、ヨウ素が含ま
れる。Halogen atoms include chlorine, bromine, fluorine, and iodine.
本発明の式(工′)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 (E) of the present invention can be produced by the following method.
A=−N−である化合物の製造
1
[式中R1、R2、Ra 、 R4、R5、R6は式(
I′)の定義と同一]
この方法は、上記方法a又はbで製造される式(IV)
の化合物に無溶媒又は不活性溶媒中式(V)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120°Cの範囲が好ましい。式(V)の
化合物は式(IV)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 a compound where A=-N- [wherein R1, R2, Ra, R4, R5, R6 are the formula (
Same as the definition of I')] This method applies to formula (IV) produced by the above method a or b.
This is carried out by reacting a compound represented by formula (V) without a solvent or in an inert solvent. The reaction temperature is preferably in the range from water cooling to about 120°C. The compound of formula (V) is preferably used in an amount equal to or more than the amount of the compound of formula (IV). At this time, triethylamine, pyridine,
The reaction proceeds smoothly when an organic or inorganic base such as sodium carbonate or sodium hydroxide is added.
本発明は式(工′)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 (E) as an active ingredient.
本発明除草剤は、前記式(工′)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和剤、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 (E) 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 formulated into wettable powders, granules, emulsions, etc. by mixing with the drug.
これらの製剤には、該化合物を有効成分として、水和剤
では10〜80%、粒剤では1〜10%、乳剤では10
〜50%(いずれも重量%を示ず)を含有することが望
ましい。These preparations contain the compound as an active ingredient, 10-80% for wettable powders, 1-10% for granules, and 10% for emulsions.
~50% (all percentages by weight are not shown).
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ブロッ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−11−メチル−8H,9H−
ベンゾ[a]ピラノ[3,2−g1キノリジン−8,9
−ジオン(化合物Nα7)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-11-methyl-8H,9H-
benzo[a]pyrano[3,2-g1 quinolidine-8,9
-Production of dione (compound Nα7).
イソキノリン2.50gとベンゼン3mlの溶液に水冷
下ジケテン5mlを約15分かけて滴下した。滴下終了
後、加温して4時間還流させた。反応混合物を冷却し析
出した結晶をろ過、乾燥させ連記化合物を1.89g得
た。5 ml of diketene was added dropwise to a solution of 2.50 g of isoquinoline and 3 ml of benzene over about 15 minutes while cooling with water. After the dropwise addition was completed, the mixture was heated and refluxed for 4 hours. The reaction mixture was cooled, and the precipitated crystals were filtered and dried to obtain 1.89 g of the compound mentioned above.
融点 220〜221°C
合成例2
6a、7−シヒドロー9−メチル−1LH,12H−ベ
ンゾ[0ピラノ[2,3−blキノリジン−11,12
−ジオン(化合物Nα5)の製造。Melting point 220-221°C Synthesis example 2 6a,7-sihydro9-methyl-1LH,12H-benzo[0pyrano[2,3-bl quinolidine-11,12
-Production of dione (compound Nα5).
キノリン5.OOgとベンゼン7.5mlの溶液にジケ
テン15m1を加え4時間還流させた。反応混合物を冷
却し析出した結晶をろ過、乾燥させ連記化合物を6.0
4g得た。Quinoline 5. 15 ml of diketene was added to a solution of OOg and 7.5 ml of benzene, and the mixture was refluxed for 4 hours. The reaction mixture was cooled, the precipitated crystals were filtered and dried, and the compound was reduced to 6.0
I got 4g.
融点 225〜231°C
同様にそれぞれ反応するキノリン類から次の化合物を得
た。Melting point: 225-231°C Similarly, the following compounds were obtained from the respective reacting quinolines.
Nα6)
融点 221;5°C(分解)
3−クロロ−6a、7ジヒドロー9−メチル−11H,
12H−ベンゾ[f1ピラノ[2,3−blキノリジン
−11,12−ジオン(化合物Nα9)
融点 251〜252°C(分解)
IR(KBrディスク): 855 、1168 、1
318 、1445 。Nα6) Melting point 221; 5°C (decomposed) 3-chloro-6a, 7 dihydro 9-methyl-11H,
12H-benzo[f1 pyrano[2,3-bl quinolidine-11,12-dione (compound Nα9) Melting point 251-252°C (decomposed) IR (KBr disk): 855, 1168, 1
318, 1445.
1690cm−1 合成例3 13.13a−ジヒド gl[L6]ナフチリ 翫1)の製造。1690cm-1 Synthesis example 3 13.13a-dihydro gl [L6] Naftiri Manufacture of rod 1).
ロー11−メチル−8H−イソキノ(2,1−ジン−8
,9(12H)−ジオン(化合物13.13a−ジヒド
ロ−11−メチル−8H,9H−ベンゾ[alピラノ[
3,2−g1キノリジン−8,9−ジオン1.OOg、
濃アンモニア水0.39m1及び水30m1の混合物を
45°Cで15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、さらに酢酸エチルと塩化メチレンの
混合物から再結晶することにより連記化合物を382m
g得た。rho-11-methyl-8H-isoquino(2,1-dine-8
,9(12H)-dione (compound 13.13a-dihydro-11-methyl-8H,9H-benzo[alpyrano[
3,2-g1 quinolidine-8,9-dione 1. OOg,
A mixture of 0.39 ml of concentrated ammonia water and 30 ml of water was stirred at 45°C for 15 hours. After cooling the reaction mixture, the precipitated crystals were treated with silica gel column chromatography and further recrystallized from a mixture of ethyl acetate and methylene chloride to obtain the compound 382m
I got g.
融点 186〜18’15°C
IR(KBrディスク): 785 、1250 、1
465 、1598 。Melting point 186~18'15°C IR (KBr disk): 785, 1250, 1
465, 1598.
16401650cm’
NMR(CDC13)δ値:
2.48(s 、 3H) 、 3.10−4.00(
m 、 2H) 、 5.26(q 、 IH) 。16401650 cm' NMR (CDC13) δ value: 2.48 (s, 3H), 3.10-4.00 (
m, 2H), 5.26(q, IH).
5.95(d 、 IH) 、 6.61(s 、 I
H) 、 6.80−7.50(m 、 5H) 。5.95 (d, IH), 6.61 (s, I
H), 6.80-7.50 (m, 5H).
12.57(s 、 IH)
合成例4
6a、7−シヒドロー9−メチル−11H−キノ[1,
2−gl[L6]す6a、7−シヒドロー9−メチル−
1LH,12H−ベンゾ[0ピラノ[2,3−blキノ
リジン−11,12−ジオン1.50g、濃アンモニア
水0.43m1及び水30m1の混合物を55°Cで1
3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、さらに酢酸エチルとl・キサンの混合物から再結
晶することにより連記化・ε1−物を332mg得た。12.57(s, IH) Synthesis Example 4 6a,7-sihydro9-methyl-11H-quino[1,
2-gl[L6]su6a,7-sihydro9-methyl-
A mixture of 1.50 g of 1LH,12H-benzo[0pyrano[2,3-bl quinolidine-11,12-dione, 0.43 ml of concentrated aqueous ammonia and 30 ml of water] was prepared at 55°C.
It was stirred for 3 hours. After cooling the reaction mixture, the precipitated crystals were treated with silica gel column chromatography and further recrystallized from a mixture of ethyl acetate and l.xane to obtain 332 mg of the compound ε1-.
融点 162.5〜164°C 同様に、それぞれ対応する原料から次の化合物を得た。Melting point: 162.5-164°C Similarly, the following compounds were obtained from the corresponding raw materials.
なお、化合物Nα8の製造においては、アンモニア水の
代わりに40%メチルアミン水溶液を用いる。Note that in the production of compound Nα8, a 40% methylamine aqueous solution is used instead of aqueous ammonia.
3−クロロ−6a、7−シヒドロー9−メチル−11H
−キノ[1,2−gl[L6]ナフチリジン−11,1
2(8H)−ジオン(化合物3)。3-chloro-6a,7-sihydro-9-methyl-11H
-quino[1,2-gl[L6]naphthyridine-11,1
2(8H)-dione (compound 3).
融点 186.5〜188.5°C
IR(KBrディスク): 1200 、1260 、
1380 、1482 。Melting point 186.5-188.5°C IR (KBr disk): 1200, 1260,
1380, 1482.
1605 1652cm’
NMR(CDC1a)δ値:
2.4.6(s 、 3H) 、 3.30(d 、
2H) 、 4.50−5.00(m 、 LH) 。1605 1652 cm' NMR (CDC1a) δ value: 2.4.6 (s, 3H), 3.30 (d,
2H), 4.50-5.00 (m, LH).
5.85(q 、 IH) 、 6.42(q 、 I
H) 、 6.97−7.33(m 、 2H) 。5.85 (q, IH), 6.42 (q, I
H), 6.97-7.33 (m, 2H).
8.07(d 、 LH) 、 8.50−12.00
(br 、 IH)6a、7−シヒドロー5,9−ジメ
チル−11H−キノ[1,2−gl[1,6]ナフチリ
ジン−11,12−(8H)−ジオン(化合物歯4)。8.07 (d, LH), 8.50-12.00
(br, IH) 6a,7-cyhydro5,9-dimethyl-11H-quino[1,2-gl[1,6]naphthyridine-11,12-(8H)-dione (compound tooth 4).
融点 138.5〜140.5°C
IR(KBrディスク): 1208 、1443 、
1485 、1580 。Melting point 138.5-140.5°C IR (KBr disk): 1208, 1443,
1485, 1580.
1650cm’
NMR(CDC13)δ値:
2.00−2.22(m 、 3H) 、 2.39(
s 、 3H) 、 2.90−3.80(m 。1650 cm' NMR (CDC13) δ value: 2.00-2.22 (m, 3H), 2.39 (
s, 3H), 2.90-3.80 (m.
2H) 、 4.40−4.90(m 、 IH) 、
5.60−5.85(m 、 IH) 。2H), 4.40-4.90 (m, IH),
5.60-5.85 (m, IH).
6.63(s 、 IH) 、 7.00−8.20(
m 、 4H)6a、7−シヒドロー8,9−ジメチル
−11H−キノ[1,2−gl[1,6]ナフチリジン
−11,12(8H)−ジオン(化合物Nα8)融点
300°C以上
IR(KBrディスク): 782 、852 、11
90 、1275 。6.63 (s, IH), 7.00-8.20 (
m, 4H) 6a,7-sihydro8,9-dimethyl-11H-quino[1,2-gl[1,6]naphthyridine-11,12(8H)-dione (compound Nα8) melting point
IR above 300°C (KBr disk): 782, 852, 11
90, 1275.
1358 、1483 、1555 、1625 。1358, 1483, 1555, 1625.
1675cm−1
(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)、ツル
ポール−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、上記水和剤分
数液を添加し、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。1675 cm-1 (Test example) Plant physiological activity test Talc (50 parts by weight), bentonite (25 parts by weight),
A carrier was prepared by mixing Tsurupol-9047 (manufactured by Toho Chemical Co., Ltd., 2 parts by weight) and Tsurupol-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 containing germinated rice, wildflower, Japanese radish, and firefly seeds, add the above-mentioned hydrating agent fraction, 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は水素
原子あるいは低級アルキル基;R_3、R_4、R_5
及びR_6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;m及びnは0もしくは1を
示す。ただし、mもしくはnは同時に0もしくは1にな
ることはなく、またR_1及びR_2が水素原子でnが
1の場合、R_3、R_4、R_5及びR_6のすべて
が同時になることない。]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 is a hydrogen atom or a lower alkyl group; R_3, R_4, R_5
and R_6 are the same or different and represent a hydrogen atom, a halogen atom, or a lower alkyl group; m and n represent 0 or 1; However, m or n will never become 0 or 1 at the same time, and if R_1 and R_2 are hydrogen atoms and n is 1, R_3, R_4, R_5, and R_6 will never become all at the same time. ] 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は水素原子あるいは低級アルキル基;R_3
、R_4、R_5及びR_6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;m及びn
は0もしくは1を示す。ただし、mもしくはnは同時に
0もしくは1になることはない。]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 is a hydrogen atom or a lower alkyl group; R_3
, R_4, R_5 and R_6 are the same or different hydrogen atom, halogen atom or lower alkyl group; m and n
indicates 0 or 1. However, m or n cannot be 0 or 1 at the same time. ] 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 |
---|---|---|---|
JP28850689A JPH03151386A (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 |
---|---|---|---|
JP28850689A JPH03151386A (en) | 1989-11-06 | 1989-11-06 | New tetracyclic condensed heterocyclic compound and herbicide |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH03151386A true JPH03151386A (en) | 1991-06-27 |
Family
ID=17731107
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP28850689A Pending JPH03151386A (en) | 1989-11-06 | 1989-11-06 | New tetracyclic condensed heterocyclic compound and herbicide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH03151386A (en) |
-
1989
- 1989-11-06 JP JP28850689A patent/JPH03151386A/en active Pending
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