JPH01121279A - Carbamoyltriazole derivative, production thereof and herbicide containing said derivative as active ingredient - Google Patents
Carbamoyltriazole derivative, production thereof and herbicide containing said derivative as active ingredientInfo
- Publication number
- JPH01121279A JPH01121279A JP27958487A JP27958487A JPH01121279A JP H01121279 A JPH01121279 A JP H01121279A JP 27958487 A JP27958487 A JP 27958487A JP 27958487 A JP27958487 A JP 27958487A JP H01121279 A JPH01121279 A JP H01121279A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- general formula
- carbamoyltriazole
- derivative
- 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.)
- Granted
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 20
- OSKSVLBJJXQUPI-UHFFFAOYSA-N 2h-triazole-4-carboxamide Chemical class NC(=O)C1=CNN=N1 OSKSVLBJJXQUPI-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000004009 herbicide Substances 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 239000004480 active ingredient Substances 0.000 title claims description 11
- -1 nitro, amino Chemical group 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 7
- 150000003852 triazoles Chemical class 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 1
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- 238000011282 treatment Methods 0.000 description 24
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- 238000006243 chemical reaction Methods 0.000 description 10
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- 238000001816 cooling Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 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
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 235000014774 prunus Nutrition 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- 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、新規なカルバモイルトリアゾール誘導体、そ
の製造法およびそれを有効成分とする除草剤に関するも
のである。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a novel carbamoyltriazole derivative, a method for producing the same, and a herbicide containing the same as an active ingredient.
〈従来の技術〉
これ迄、特開昭59−89880号公報、米国特許第4
280881号明細書等にある種のカルバモイルトリア
ゾール誘導体が、除草剤の有効成分として用いうろこと
が記載されている。<Prior art> Until now, Japanese Patent Application Laid-Open No. 59-89880, U.S. Patent No. 4
No. 280881 and other documents describe that certain carbamoyltriazole derivatives can be used as active ingredients of herbicides.
〈発明が解決しようとする問題点〉
しかしながら、これらの化合物は、除草効力が不充分で
あったり、作物・雑草間の選択性に劣ったりすることか
ら必ずしも満足すべきものとは言い難い。<Problems to be Solved by the Invention> However, these compounds are not necessarily satisfactory because their herbicidal efficacy is insufficient or their selectivity between crops and weeds is poor.
く問題点を解決するための手段〉
本発明者等は、このような状況に鑑み、種々検討した結
果、下記の一般式CI)で示されるカルバモイルトリア
ゾール誘導体が上述のような欠点の少ない、優れた除草
効力を有し、かつ作物・雑草間に優れた選択性を示す化
合物であることを見い出し、本発明に至った。In view of this situation, the present inventors have conducted various studies and found that the carbamoyltriazole derivative represented by the following general formula CI) is an excellent product with few drawbacks as described above. The inventors have discovered that the compound has excellent herbicidal efficacy and exhibits excellent selectivity between crops and weeds, leading to the present invention.
すなわち、本発明は、一般式CI)
〔式中 R1およびR2は同一または相異なり、低級ア
ルキル基、低級アルケニル基またはR1とR2とで環を
なす低級アルキレン基を表わし、XおよびYは同一また
は相異なり、水素原子、ハロゲン原子、低級アルキル基
、低級アルコキシ基、低級アルコキシカルボニル基、ニ
トロ基、アミノ基、アシルアミノ基またはトリフルオロ
メチル基を表わし、nは0.1または2の整数を表わす
。但し R1とR2とが共にメチル基であるものは除く
。〕
で示されるカルバモイルトリアゾール誘導体(以下、本
発明化合物と記す。)、その製造法およびそれを有効成
分とする除草剤を提供するものである。That is, the present invention relates to the general formula CI) [wherein R1 and R2 are the same or different and represent a lower alkyl group, a lower alkenyl group, or a lower alkylene group in which R1 and R2 form a ring, and X and Y are the same or Differently, it represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group, a nitro group, an amino group, an acylamino group or a trifluoromethyl group, and n represents an integer of 0.1 or 2. However, those in which R1 and R2 are both methyl groups are excluded. ] The present invention provides a carbamoyltriazole derivative represented by (hereinafter referred to as the compound of the present invention), a method for producing the same, and a herbicide containing the same as an active ingredient.
次にその製造法について詳しく説明する。Next, the manufacturing method will be explained in detail.
本発明化合物は、一般式CI)
〔式中、X、Yおよびnは前記と同じ意味を表わす。〕
で示されるトリアゾール誘導体と一般式〔I)〔式中
R1およびR2は前記と同じ意味を表わし、Zはハロゲ
ン原子を表わす。〕
で示されるカルバモイルハライドとを反応させることに
よって製造することができる。The compound of the present invention has the general formula CI) [wherein X, Y and n represent the same meanings as above. ] The triazole derivative represented by the general formula [I] [in the formula
R1 and R2 have the same meanings as above, and Z represents a halogen atom. ] It can be produced by reacting with the carbamoyl halide shown below.
との反応は、通常、溶媒中、脱ハロゲン化水素剤の存在
下で行い、反応温度の範囲は0〜150℃、反応時間の
範囲は10分〜24時間であり、反応に供される試剤の
量は、トリアゾール誘導体〔I〕1当量に対してカルバ
モイルハライド(1)は1〜1.5当量、脱ハロゲン化
水素剤は1〜5当量である。The reaction with is usually carried out in a solvent in the presence of a dehydrohalogenating agent, the reaction temperature range is 0 to 150°C, the reaction time is 10 minutes to 24 hours, and the reaction time is 10 minutes to 24 hours. The amount of the carbamoyl halide (1) is 1 to 1.5 equivalents, and the amount of the dehydrohalogenation agent is 1 to 5 equivalents per 1 equivalent of the triazole derivative [I].
溶媒としては、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類、ベンゼン、トルエン、
キシレン等の芳香族炭化水素類、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
ゼン等のハロゲン化炭化水素類、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のエーテ
ル類、アセトン、メチルエチルケトン、メチルイソブチ
ルケトン、イソホロン、シクロヘキサノン等のケトン類
、ニトロエタン、ニトロベンゼン等のニトロ化合物、ア
セトニトリル、イソブチロニトリル等のニトリル類、ピ
リジン、トリエチルアミン、N、N−ジエチルアニリン
、トリブチルア廻ン、N−メチルモルホリン等の第三級
アミン、N、N−ジメチルホルムアミド等の酸アミド、
ジメチルスルホキシド、スルホラン等の硫黄化合物等、
あるいはそれらの混合物があげられる。As a solvent, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, benzene, toluene,
Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, acetone, methyl ethyl ketone, Ketones such as methyl isobutyl ketone, isophorone, and cyclohexanone, nitro compounds such as nitroethane and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile, pyridine, triethylamine, N,N-diethylaniline, tributylamine, and N-methylmorpholine. tertiary amines such as, acid amides such as N,N-dimethylformamide,
Sulfur compounds such as dimethyl sulfoxide and sulfolane, etc.
Or a mixture thereof.
脱ハロゲン化水素剤としては、ピリジン、トリエチルア
ミン、N、N−ジエチルアニリン等の有機塩等、水酸化
ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カ
リウム、水素化ナトリウム等の無機塩基、ナトリウムメ
トキシド、ナトリウムエトキシド等のアルカリ金属アル
コキシド等があげられる。反応終了後の反応液は、水を
加えて、有機溶媒抽出および濃縮等の通常の後処理を行
い、必要ならば、クロマトグラフィー、再結晶等の操作
によって精製することもできる。Examples of the dehydrohalogenation agent include organic salts such as pyridine, triethylamine, and N,N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and sodium hydride, sodium methoxide, Examples include alkali metal alkoxides such as sodium ethoxide. After completion of the reaction, the reaction solution is subjected to conventional post-treatments such as addition of water, organic solvent extraction and concentration, and, if necessary, can be purified by operations such as chromatography and recrystallization.
また、一般式〔I〕においてnが1または2である化合
物は一般式〔I′〕
〔式中 R1、R”、XおよびYは前記と同じ意味を表
わず。〕
で示されるカルバモイルトリアゾール誘導体を酸化する
ことにより製造することもできる。In addition, the compound in which n is 1 or 2 in the general formula [I] is a carbamoyltriazole represented by the general formula [I'] [wherein R1, R", X and Y do not have the same meanings as above.] It can also be produced by oxidizing a derivative.
このとき、用いられる酸化剤としては、メタクロロ過安
息香酸等の芳香族過酸、過酢酸、過トリフルオロ酢酸等
の脂肪族過酸、過酸化水素等があげられる。該反応は通
常溶媒中で行われ、用いられる溶媒は酸化剤の種類によ
り異なり、例えば過酸化水素ならば水、酢酸、アセトン
等が、芳香族過酸ならばクロロホルム、塩化メチレン等
のハロゲン化炭化水素類や、ジエチルエーテル、ジオキ
サン等のエーテル類、脂肪族過酸ならば対応するカルボ
ン酸が通常用いられる。Examples of the oxidizing agent used at this time include aromatic peracids such as metachloroperbenzoic acid, aliphatic peracids such as peracetic acid and pertrifluoroacetic acid, and hydrogen peroxide. The reaction is usually carried out in a solvent, and the solvent used varies depending on the type of oxidizing agent. For example, water, acetic acid, acetone, etc. are used for hydrogen peroxide, and halogenated carbonates such as chloroform, methylene chloride, etc. are used for aromatic peracids. Hydrogens, ethers such as diethyl ether and dioxane, and, in the case of aliphatic peracids, the corresponding carboxylic acids are usually used.
反応温度の範囲は、通常0〜100℃、反応時間の範囲
は通常10分〜24時間であり、反応に用いられる試剤
の量は、カルバモイルトリアゾール誘導体CI’)1当
量に対して酸化剤は通常1〜5当量であるが、一般式C
I)においてn=1で示されるものの製造においては、
通常0°C〜室温下に0.9〜1.2当量の酸化剤を用
いて行い、n=2で、示されるものの製造においては、
通常室温〜100℃で2〜5当量の酸化剤を用いて行う
。The reaction temperature range is usually 0 to 100°C, the reaction time is usually 10 minutes to 24 hours, and the amount of reagent used in the reaction is usually 1 equivalent of carbamoyltriazole derivative CI'). 1 to 5 equivalents, but general formula C
In the production of the product indicated by n=1 in I),
Usually carried out at 0°C to room temperature using 0.9 to 1.2 equivalents of oxidizing agent, n = 2, and in the production of the indicated product,
It is usually carried out at room temperature to 100°C using 2 to 5 equivalents of an oxidizing agent.
反応終了後は、水を加えて有機溶媒抽出および濃縮等の
通常の後処理を行い目的化合物を得る。また、必要によ
りクロマトグラフィー、再結晶等の操作を行う。After the reaction is completed, water is added and conventional post-treatments such as organic solvent extraction and concentration are performed to obtain the target compound. In addition, operations such as chromatography and recrystallization are performed as necessary.
本発明化合物を製造する場合、原料化合物である一般式
CI)で示されるトリアゾール誘導体のうちnが1また
は2であるものは、nが0であるものを上記の方法に準
じて酸化することにより製造される。When producing the compound of the present invention, triazole derivatives represented by the general formula CI), which are starting compounds, where n is 1 or 2 can be prepared by oxidizing those where n is 0 according to the above method. Manufactured.
また、一般式(II)で示されるトリアゾール誘導体の
うちnが0であるものは一般式IJ)〔式中、Xおよび
Yは前記と同じ意味を表わし、Wはハロゲン原子、H3
O4、No、またはClO4を表わす。〕
で示されるジアゾニウム塩と一般式CD〔式中、Mはア
ルカリ金属を表わす。〕で示される化合物とを反応させ
ることにより製造することができる。Furthermore, among the triazole derivatives represented by the general formula (II), those in which n is 0 have the general formula IJ) [wherein, X and Y represent the same meanings as above, W is a halogen atom, H3
Represents O4, No, or ClO4. ] A diazonium salt represented by the general formula CD [where M represents an alkali metal]. ] It can be produced by reacting with the compound shown below.
また、n=0である一般式(1)で示されるトリアゾー
ル誘導体のあるものは一般式〔■〕〔式中、x′および
Y′は同一または相異なり、水素原子、ハロゲン原子、
ニトロ基またはトリフルオロメチル基を表わし、■はハ
ロゲン原子を表わす。但し、x′とY′ とが共に水素
原子であるものは除く。〕
で示される化合物と8−メルカプト−LH−1゜2.4
−)リアゾールとを塩基の存在下に反応させることによ
り製造することもできる。Further, some triazole derivatives represented by the general formula (1) where n=0 have the general formula [■] [where x' and Y' are the same or different, a hydrogen atom, a halogen atom,
It represents a nitro group or a trifluoromethyl group, and ■ represents a halogen atom. However, cases in which x' and Y' are both hydrogen atoms are excluded. ] The compound shown and 8-mercapto-LH-1゜2.4
-) It can also be produced by reacting with lyazole in the presence of a base.
用いられる塩基としては、例えば、水酸化ナトリウム、
水酸化カリウム、炭酸ナトリウム、炭酸カリウム、水素
化ナトリウム、ナトリウムメトキシド、ナトリウムエト
キシド等があげられる。Examples of the base used include sodium hydroxide,
Examples include potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride, sodium methoxide, and sodium ethoxide.
また、該反応を行う際に触媒量の銅化合物等を添加する
こともできる。Further, a catalytic amount of a copper compound or the like may be added when carrying out the reaction.
本発明化合物は、優れた除草効力を有し、かつ作物・雑
草間に優れた選択性を示す。すなわち本発明化合物は、
畑地の茎葉処理および土壌処理において、問題となる種
々の雑草、例えば、ソバカズラ、サナエタデ、スベリヒ
ュ、ハコベ、シロザ、アオゲイトウ、ダイコン、ノハラ
ガラシ、ナズナ、アメリカツノクサネム、イチビ、アメ
リカキンゴジカ、フィールドパンジー、アメリカアサガ
オ、マルバアザガオ、セイヨウヒルガオ、ヒメオドリコ
ソウ、ホトケノザ、シロバナチロウセンアサガオ、イヌ
ホオズキ、オオイヌノフグリ、イヌカミツレ、コーンマ
リーゴールド等の広葉雑草、ヒエ、イヌビエ、エノコロ
グサ、メヒシバ、スズメノカタビラ、ノスズメノテッポ
ウ、エンバク、カラスムギ、セイバンモロコシ、シバム
ギ、ウマノチャヒキ、ギ目つギシバ等のイネ科雑草およ
びツユクサ等のツユクサ科雑草、コゴメガヤツリ、ハマ
スゲ等のカヤツリグサ科雑草等に対して除草効力を有し
、しかも本発明化合物は、トウモロコシ、コムギ、イネ
、ダイズ、ワタ、テンサイ等の主要作物に対して問題と
なるような薬害を示さない。The compounds of the present invention have excellent herbicidal efficacy and exhibit excellent selectivity between crops and weeds. That is, the compound of the present invention is
Various weeds that are problematic in the treatment of foliage and soil in upland fields, such as freckles, Japanese knotweed, purslane, chickweed, white radish, Japanese radish, daikon radish, shepherd's purse, shepherd's purse, American hornwort, field pansy, American goldenrod, field pansy, American Broad-leaved weeds such as morning glory, morning glory, European bindweed, Japanese oatweed, white-breasted morning glory, Japanese oat, Japanese oat, corn marigold, etc., barnyard grass, Japanese millet, foxtail grass, black-seed grass, sycamore, Japanese sorghum, oat, oat, Seiban sorghum , The compound of the present invention has a herbicidal effect on weeds of the grass family, such as grasshopper, grasshopper, and cypress, as well as weeds of the cyperaceae family, such as dayflower, and cypressweeds, such as cyperus spp. It does not cause any harmful effects on major crops such as soybean, cotton, and sugar beet.
また、本発明化合物は、水田の湛水処理において、問題
となる種々の雑草、例えば、タイヌビエ等のイネ科雑草
、アゼナ、キカシグサ、ミゾハコベ等の広葉雑草、クマ
ガヤツリ、ホタルイ、マツバイ、ミズガヤツリ等のカヤ
ツリグサ科雑草、コナギ、ウリカワ等に対して除草効力
を有し、しかもイネに対しては問題となるような薬害を
示さない。In addition, the compound of the present invention can be applied to various weeds that are problematic in the waterlogging treatment of rice fields, such as grass weeds such as Japanese grasshopper, broad-leaved weeds such as azalea, commonweed, and chickweed, and cypress weeds such as cypress It has a herbicidal effect on weeds of the same family, such as Physcomitrella sinensis and Prunus elegans, and does not cause any problematic phytotoxicity to rice.
本発明化合物を除草剤の有効成分として用いる場合は、
通常固体担体、液体担体、界面活性剤その他の製剤用補
助剤と混合して、乳剤、水和剤、懸濁剤、粒剤等に製剤
して用いる。When using the compound of the present invention as an active ingredient of a herbicide,
It is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to formulate emulsions, wettable powders, suspensions, granules, and the like.
これらの製剤には有効成分として本発明化合物を、重量
比で0.1〜90%、好ましくは0.2〜80%含有す
る。These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 90%, preferably 0.2 to 80%.
固体担体としては、カオリンクレー、アッタパルジャイ
トクレー、ベントナイト、酸性白土、パイロフィライト
、タルク、珪藻土、方解石、クル主殻粉、尿素、硫酸ア
ンモニウム、合成含水酸化珪素等の微粉末あるいは粒状
物があげられ、液体担体としては、キシレン、メチルナ
フタレン等の芳香族炭化水素類、イソプロパツール、エ
チレングリコール、セロソルブ等のアルコール類、アセ
トン、シクロヘキサノン、イソホロン等のケトン類、大
豆油、綿実油等の植物油、ジメチルスルホキシド、N、
N−ジメチルホルムア主ド、アセトニトリル、水等があ
げられる。Examples of solid carriers include fine powders or granules such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, Kulu main shell powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, and vegetable oils such as soybean oil and cottonseed oil. dimethyl sulfoxide, N,
Examples include N-dimethylformamide, acetonitrile, and water.
乳化、分散、湿層等のために用いられる界面活性剤とし
ては、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、ジアルキルスルホコ
ハク酸塩、ポリオキシエチレンアルキルアリールエーテ
ルリン酸エステル塩等の陰イオン界面活性剤、ポリオキ
シエチレンアルキルエーテル、ポリオサシエチレンアル
キルアリールエーテル、ポリオキシエチレンポリオキシ
プロピレンブロックコポリマー、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等
の非イオン界面活性剤等があげられる。Surfactants used for emulsification, dispersion, wetting layers, etc. include alkyl sulfate salts, alkyl sulfonate salts, alkylaryl sulfonate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphate salts, etc. Nonionic surfactants such as anionic surfactants, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, etc. .
その他の製剤用補助剤としては、リグニンスルホン酸塩
、アルギン酸塩、ポリビニルアルコール、アラビアガム
、CMC(カルボキシメチルセルロース)、PAP(酸
性リン酸イソプロピル)等があげられる。Other formulation adjuvants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate), and the like.
本発明化合物は、通常製剤化して雑草の出芽前または出
芽後に土壌処理、茎葉処理または湛水処理する。土壌処
理には、土壌表面処理、土壌混和処理等があり、茎葉処
理には、植物体の上方からの処理のほか、作物に付着し
ないよう雑草に限って処理する局部処理等がある。The compound of the present invention is usually formulated and treated with soil, foliage, or flooding before or after the emergence of weeds. Soil treatment includes soil surface treatment, soil mixing treatment, etc., and foliage treatment includes treatment from above the plant body, as well as local treatment that treats only weeds so that they do not attach to crops.
また他の除草剤と混合して用いることにより、除草効力
の増強を期待できる。さらに、殺虫剤、殺ダニ剤、殺線
虫剤、殺菌剤、植物生長調節剤、肥料、土壌改良剤等と
混合して用いることもできる。Further, by mixing it with other herbicides, it can be expected to increase the herbicidal efficacy. Furthermore, it can be used in combination with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners, and the like.
なお、本発明化合物は、水田、畑地、果樹園、牧草地、
芝生地、森林あるいは非農耕地の有効成分として用いる
ことができる。The compound of the present invention can be used in rice fields, fields, orchards, pastures,
It can be used as an active ingredient in lawns, forests or non-agricultural lands.
本発明化合物を除草剤の有効成分として用いる場合、そ
の処理量は、気象条件、製剤形態、処理時期、方法、場
所、対象雑草、対象作物等によっても異なるが、通常1
アールあたり0.2f〜200 f1好ましくは0.5
f〜10(1’であり、乳剤、水和剤、懸濁剤等は、通
常その所定量を1アールあたり1リツトル〜10リツト
ルの(必要ならば、展着剤等の補助剤を添加した)水で
希釈して処理し、粒剤等は、通常なんら希釈することな
くそのまま処理する。When the compound of the present invention is used as an active ingredient of a herbicide, the amount to be treated will vary depending on weather conditions, formulation form, treatment time, method, location, target weeds, target crops, etc., but usually 1.
0.2f to 200 f1 preferably 0.5 per are
f to 10 (1'), and emulsions, wetting agents, suspending agents, etc. are usually used in a specified amount of 1 liter to 10 liters per are (if necessary, auxiliary agents such as spreading agents are added). ) It is treated by diluting it with water, and granules etc. are usually treated as they are without any dilution.
展着剤としては、前記の界面活性剤のほか、ポリオキシ
エチレン樹脂酸(エステル)、リグニンスルホン酸塩、
アビエチン酸塩、ジナフチルメタンジスルホン酸塩、パ
ラフィン等があげられる。In addition to the above-mentioned surfactants, the spreading agents include polyoxyethylene resin acid (ester), lignin sulfonate,
Examples include abietate, dinaphthylmethane disulfonate, and paraffin.
〈実施例〉
以下、本発明を製造例、製剤例および試験例により、さ
らに詳しく説明するが、本発明はこれらの実施例のみに
限定されるものではない。<Examples> Hereinafter, the present invention will be explained in more detail with reference to production examples, formulation examples, and test examples, but the present invention is not limited only to these examples.
まず、本発明化合物の製造例を示す。First, a production example of the compound of the present invention will be shown.
製造例1
8−(8−メトキシ−5−トリフルオロメチルフェニル
チオ)−1,2,4−トリアゾール 2.44Nをピリ
ジン20+lに溶かし、ジエチルカルバモイルクロリド
1.45fulllえ室温で12時間撹拌した。次に、
減圧下でピリジンを留去し、残渣に酢酸エチルを加え、
1規定塩酸、次いで、飽和食塩水で8回洗浄した。無水
硫酸マグネシウムで乾燥した後減圧下に溶媒を留去して
1−(ジエチルカルバモイル)−8−(8−メトキシ−
5−トリフルオロメチルフェニルチオ)−1,2,4−
トリアゾール8.40fを得た。Production Example 1 2.44N of 8-(8-methoxy-5-trifluoromethylphenylthio)-1,2,4-triazole was dissolved in 20+l of pyridine, 1.45 full of diethylcarbamoyl chloride was added, and the mixture was stirred at room temperature for 12 hours. next,
Pyridine was distilled off under reduced pressure, ethyl acetate was added to the residue,
It was washed eight times with 1N hydrochloric acid and then with saturated saline. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 1-(diethylcarbamoyl)-8-(8-methoxy-
5-trifluoromethylphenylthio)-1,2,4-
Triazole 8.40f was obtained.
n、 1.5215
製造例2
1−ジエチルカルバモイル−8−(2−メチルフェニル
チオ)−1,2,4−)リアゾール 1.4TIをクロ
ロホルム120 yxlに溶かし、メタクロロ過安息香
酸(含量70%)1.25fをクロロホルム20 te
lに溶かした液を0〜5°Cで滴下した。0〜5°Cで
1時間撹拌した後、20%炭酸カリウム水溶液で8回洗
浄し、次いで飽和食塩水で2回洗浄した。n, 1.5215 Production Example 2 1-Diethylcarbamoyl-8-(2-methylphenylthio)-1,2,4-)riazole 1.4TI was dissolved in 120 yxl of chloroform, and metachloroperbenzoic acid (content 70%) was dissolved. 1.25f in chloroform 20te
The solution was added dropwise at 0 to 5°C. After stirring at 0 to 5°C for 1 hour, the mixture was washed eight times with a 20% aqueous potassium carbonate solution, and then twice with saturated brine.
無水硫酸マグネシウムで乾燥した後溶媒を減圧下に留去
して1−ジエチルカルバモイル−8−(2−メチルフェ
ニルスルフィニル)−1.2.4−トリアゾール1.2
Ofを得た。After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 1-diethylcarbamoyl-8-(2-methylphenylsulfinyl)-1.2.4-triazole 1.2
I got Of.
nD 1.5688
製造例8
1−ジエチルカルバモイル・−8−(8−クロロフェニ
ルチオ)−1,2,4−トリアゾール 1.09fをク
ロロホルム120 ylに溶かし、メタクロロ過安息香
酸(含R70%)2、16 fを加え、室温で12時間
撹拌した。nD 1.5688 Production Example 8 1-diethylcarbamoyl-8-(8-chlorophenylthio)-1,2,4-triazole 1.09f was dissolved in 120 yl of chloroform, and metachloroperbenzoic acid (R content 70%) 2, 16 f was added and stirred at room temperature for 12 hours.
20%炭酸カリウム水溶液で8回洗浄し、次いで飽和食
塩水で2回洗浄した。無水硫酸マグネシウムで乾燥した
後、溶媒を減圧下に留去して得た残渣をベンゼン、ヘキ
サン混合溶媒より再結晶して1−ジエチルカルバモイル
−8−(8−クロロフェニルスルホニル)−1,2,4
−トリアゾール0.98gを得た。It was washed eight times with a 20% aqueous potassium carbonate solution, and then twice with saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was recrystallized from a mixed solvent of benzene and hexane to give 1-diethylcarbamoyl-8-(8-chlorophenylsulfonyl)-1,2,4.
-0.98 g of triazole was obtained.
融点 118.0〜120.0℃
次に、上記の方法に準じて製造された本発明化合物のい
くつかを第1表に示す。Melting point: 118.0-120.0°C Next, Table 1 shows some of the compounds of the present invention produced according to the above method.
次に、原料化合物であるトリアゾール誘導体(1)の製
造例を参考例にて示す。Next, a production example of the triazole derivative (1), which is a raw material compound, will be shown as a reference example.
参考例1
8−トリフルオロメチルアニリン14.5Ofに水15
0 mlおよび濃塩酸20.4s/を加えた。0〜5℃
で撹拌しながら亜硝酸ナトリウム6.90fを水20g
/に溶かした液を加え、さらに20分間撹拌を続けた。Reference example 1 8-trifluoromethylaniline 14.5Of water 15
0 ml and 20.4 s/concentrated hydrochloric acid were added. 0~5℃
Add 6.90f of sodium nitrite to 20g of water while stirring with
The solution dissolved in / was added, and stirring was continued for an additional 20 minutes.
26%水酸化ナトリウム水溶液で中和した後、メタノー
ル50耐に水酸化カリウム7、92 Fおよび8−メル
カプト−IH−1,2,4−)リアゾール12.12
Fを溶かした液を滴下した。0〜5°Cで2時間、次い
で室温で1時間撹拌した。After neutralization with 26% aqueous sodium hydroxide solution, potassium hydroxide 7,92F and 8-mercapto-IH-1,2,4-) lyazole 12.12% in methanol 50 resistant.
A solution containing F was added dropwise. Stirred at 0-5°C for 2 hours and then at room temperature for 1 hour.
反応液に食塩を加えて飽和し、酢酸エチルで抽出した。The reaction solution was saturated with sodium chloride and extracted with ethyl acetate.
酢酸エチル層を飽和食塩水で2回洗浄し、無水硫酸マグ
ネシウムで乾燥した。The ethyl acetate layer was washed twice with saturated brine and dried over anhydrous magnesium sulfate.
溶媒を減圧下に留去して得た残渣をカラムクロマトグラ
フィーにて処理し8−(8−)リフルオロメチルフェニ
ルチオ)−1,2,4−トリアゾール15.80fを得
た。The residue obtained by distilling off the solvent under reduced pressure was treated with column chromatography to obtain 15.80f of 8-(8-)lifluoromethylphenylthio)-1,2,4-triazole.
融点71.0〜72.5℃
参考例2
水素化ナトリウム(含量60%)2.00fをN、N−
ジメチルホルムアミド100 mlに懸濁させ、8−メ
ルカプト−IH−1,2゜4−トリアゾール5.05F
を加え、80分間室温で撹拌した。8.5−ビス(トリ
フルオロメチル)ブロモベンゼン14.65Fおよび触
媒量の塩化第一銅を加え、窒素雰囲気下で5時間加熱還
流した。放冷後減圧下に溶媒を留去し、酢酸エチルを加
え飽和食塩水で2回洗浄した。無水硫酸マグネシウムで
乾燥し、溶媒を減圧下に留去して得た結晶をベンゼン、
ヘキサン混合溶媒で洗浄した後減圧下に乾燥して8−(
8,5−ビス(トリフルオロメチル)フェニルチオ)−
1,2,4−)リアゾール6.00fを得た。Melting point 71.0-72.5°C Reference example 2 2.00f of sodium hydride (content 60%) was dissolved in N,N-
Suspend in 100 ml of dimethylformamide and add 8-mercapto-IH-1,2°4-triazole 5.05F.
was added and stirred at room temperature for 80 minutes. 14.65F of 8.5-bis(trifluoromethyl)bromobenzene and a catalytic amount of cuprous chloride were added, and the mixture was heated under reflux for 5 hours under a nitrogen atmosphere. After cooling, the solvent was distilled off under reduced pressure, ethyl acetate was added, and the mixture was washed twice with saturated brine. The crystals obtained by drying over anhydrous magnesium sulfate and distilling off the solvent under reduced pressure were mixed with benzene,
After washing with a hexane mixed solvent and drying under reduced pressure, 8-(
8,5-bis(trifluoromethyl)phenylthio)-
1,2,4-) Riazole 6.00f was obtained.
融点110.5〜111.0℃
上記の参考例に準じて製造されたトリアゾール誘導体(
1)のいくつかを第2表に示す。Melting point: 110.5-111.0°C Triazole derivative (
Some of 1) are shown in Table 2.
第2表
次に製剤例を示す。なお、本発明化合物は第1表の化合
物番号で示す。部は重量部である。Table 2 shows formulation examples. The compounds of the present invention are indicated by compound numbers in Table 1. Parts are parts by weight.
製剤例1
本発明化合物@50部、リグニンスルホン酸カルシウム
8部、ラウリル硫酸ナトリウム2部および合成含水酸化
珪素45部をよく粉砕混合して水和剤を得る。Formulation Example 1 50 parts of the compound of the present invention, 8 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder.
製剤例2
本発明化合物(1)〜(62)の各々10部、ポリオキ
シエチレンスチリルフェニルエーテル14部、ドデシル
ベンゼンスルホン酸カルシウム6部、キシレン80部お
よびシクロヘキサノン40部をよく混合して乳剤を得る
。Formulation Example 2 10 parts each of the compounds (1) to (62) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 80 parts of xylene and 40 parts of cyclohexanone are thoroughly mixed to obtain an emulsion. .
製剤例8
本発明化合物(88) 2部、合成含水酸化珪素1部、
リグニンスルホン酸カルシウム2部、ベントナイト80
部およびカオリンクレー65部をよく粉砕混合し、水を
加えてよく練り合せた後、造粒乾燥して粒剤を得る。Formulation Example 8 2 parts of the compound of the present invention (88), 1 part of synthetic hydrous silicon oxide,
2 parts calcium lignin sulfonate, 80 parts bentonite
1 part and 65 parts of kaolin clay are thoroughly ground and mixed, water is added and the mixture is thoroughly kneaded, and then granulated and dried to obtain granules.
製剤例4
本発明化合物(20) 25部、ポリオキシエチレンソ
ルビタンモノオレエート8部、CMC8部、水69部を
混合し、粒度が5ミクロン以下になるまで湿式粉砕して
懸濁剤を得る。Formulation Example 4 25 parts of the compound of the present invention (20), 8 parts of polyoxyethylene sorbitan monooleate, 8 parts of CMC, and 69 parts of water are mixed and wet-pulverized until the particle size becomes 5 microns or less to obtain a suspension.
次に、本発明化合物が除草剤の有効成分としく27)
て有用であることを試験例で示す。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8表の化合物記号で示す。Next, test examples will demonstrate that the compounds of the present invention are useful as active ingredients in herbicides27). 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 8.
第 8 表−
また、除草効力および薬害の評価は、調査時の供試植物
(雑草および作物)の出芽および生育の状態が無処理の
それと比較して全くないしほとんど違いがないものを「
0」 とし、供試植物が完全枯死または出芽若しくは
生育が完全に抑制されているものを「101として、θ
〜10の11段階に区分し0.1.2.8.4.5.6
.7.8.9.10で示す。Table 8 - Evaluation of herbicidal efficacy and phytotoxicity is based on whether the germination and growth conditions of the test plants (weeds and crops) at the time of the survey are completely or almost different from those of untreated plants.
If the test plant is completely dead or its budding or growth is completely suppressed, it is set as "101," and θ
Classified into 11 stages of ~100.1.2.8.4.5.6
.. 7.8.9.10.
試験例1 畑地土壌表面処理試験
直径103、深さ10αの円筒型プラスチックポットに
畑地土壌を詰め、ヒエを播種し、覆土した。製剤例2に
準じて供試化合物を乳剤にし、その所定量を1アールあ
たり10リツトル相当の水で希釈し、小型噴霧器で土壌
表面に処理した。処理後20日間温室内で育成し、除草
効力を調査した。その結果を第4表に示す。Test Example 1 Upland Soil Surface Treatment Test A cylindrical plastic pot with a diameter of 103 mm and a depth of 10 α was filled with upland soil, sown with barnyard grass, and covered with soil. The test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are, and the emulsion was applied to the soil surface using a small sprayer. After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 4.
第 4 表
試験例2 畑地茎葉処理試験
直径103、深さ11’Wの円筒型プラスチックポット
に畑地土壌を詰め、ヒエを播種し、温室内で10日間育
成した。その後、製剤例2に準じて供試化合物を乳剤に
し、その所定量を1アールあたり10リツトル相当の展
着剤を含む水で希釈し、小型噴霧器で植物体の上方から
茎葉処理した。処理後20日間温室内で育成し、除草効
力を調査した。その結果を第6表に示す。Table 4 Test Example 2 Upland Stem and Leaf Treatment Test A cylindrical plastic pot with a diameter of 103 mm and a depth of 11'W was filled with upland soil, and barnyard grass was sown and grown in a greenhouse for 10 days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water containing a spreading agent equivalent to 10 liters per are, and the foliage was treated from above the plant using a small sprayer. After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 6.
第 5 表
試験例8 水田湛水処理試験
直径8cIII、深さ121の円筒型プラスチックポッ
トに水田土壌を詰め、タイヌビエの種子を1〜23の深
さに混ぜ込んだ。湛水して水田状態にした後、温室内で
育成した。6日後(タイヌビエの発生初期)に製剤例2
に準じて供試化合物を乳剤にし、その所定量を5ミリリ
ツトルの水で希釈し、水面に処理した。Table 5 Test Example 8 Paddy field flooding treatment test A cylindrical plastic pot with a diameter of 8 cIII and a depth of 121 m was filled with paddy soil, and seeds of Japanese millet were mixed in at a depth of 1 to 23 m. After being flooded into paddy fields, they were grown in a greenhouse. Formulation Example 2 after 6 days (in the early stage of the outbreak of Japanese millet)
The test compound was made into an emulsion according to the method described above, and a predetermined amount of the emulsion was diluted with 5 milliliters of water and applied to the water surface.
処理後20日間温室内で育成し、除草効力を調査した。After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated.
その結果を第6表に示す。The results are shown in Table 6.
第 6 表
試験例4 水田湛水処理試験
115000aワグネルポツトに水田土壌を詰め、タイ
ヌビエ、広葉雑草(アゼナ、キカシグサ、ミゾハコベ)
、ホタルイの種子を1〜21の深さに混ぜ込んだ。湛水
して水田状態にした後、8葉期のイネを移植し、温室内
で育成した。4日後に、製剤例2に準じて供試化合物を
乳剤にし、その所定量をIOEリリットルの水で希釈し
水面に処理し、その水深を4c11とした。処理後20
日間温室内で育成し、除草効力および薬害を調査した。Table 6 Test Example 4 Paddy field flooding treatment test 115000a Wagner pots were filled with paddy soil and treated with Japanese millet and broad-leaved weeds (Azaena, Kikashigusa, Chickweed)
, the seeds of firefly were mixed in at a depth of 1 to 21. After flooding the rice field to create a paddy field, rice at the 8-leaf stage was transplanted and grown in a greenhouse. After 4 days, the test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount of the emulsion was diluted with IOE liter of water and applied to the water surface to a water depth of 4c11. 20 days after treatment
The plants were grown in a greenhouse for one day and their herbicidal efficacy and phytotoxicity were investigated.
その結果を第7表に示す。なお、処理の翌日から2日間
は、1日あたり8cIMの水深に相当する量の漏水をお
こなった。The results are shown in Table 7. Note that for two days from the day after the treatment, water leaked in an amount equivalent to a water depth of 8 cIM per day.
第 7 表
〈発明の効果〉
本発明化合物は、畑地の土壌処理および茎葉処理、さら
に水田の湛水処理において問題となる種々の雑草に対し
て優れた除草効力を有し、主要作物と雑草間に優れた選
択性を示すことから除草剤の有効成分として種々の用途
に用いることができる。Table 7 <Effects of the Invention> The compound of the present invention has excellent herbicidal efficacy against various weeds that are problematic in soil treatment and foliage treatment of upland fields, as well as in flooding treatment of rice fields, and has excellent herbicidal efficacy against various weeds that are problematic in soil treatment and foliage treatment of upland fields, as well as in flooding treatment of rice fields. Since it exhibits excellent selectivity for herbicides, it can be used in a variety of applications as an active ingredient in herbicides.
(89完)(89 completed)
Claims (1)
級アルキル基、低級アルケニル基または R^1とR^2とで環をなす低級アルキレン基を表わし
、XおよびYは同一または相異なり、水素原子、ハロゲ
ン原子、低級アルキル基、低級アルコキシ基、低級アル
コキシカルボニル基、ニトロ基、アミノ基、アシルアミ
ノ基またはトリフルオロメチル基を表わし、nは0、1
または2の整数を表わす。 但し、R^1とR^2とが共にメチル基であるものは除
く。〕 で示されるカルバモイルトリアゾール誘導体。 (2)一般式 ▲数式、化学式、表等があります▼ 〔式中、XおよびYは同一または相異なり、水素原子、
ハロゲン原子、低級アルキル基、低級アルコキシ基、低
級アルコキシカルボニル基、ニトロ基、アミノ基、アシ
ルアミノ基またはトリフルオロメチル基を表わし、nは
0、1または2を表わす。〕 で示されるトリアゾール誘導体と一般式 ▲数式、化学式、表等があります▼ 〔式中、R^1およびR^2は同一または相異なり、低
級アルキル基、低級アルケニル基またはR^1とR^2
とで環をなす低級アルキレン基を表わし、Zはハロゲン
原子を表わす。 但しR^1とR^2とが共にメチル基であるものは除く
。〕 で示されるカルバモイルハライドとを反応させることを
特徴とする一般式 ▲数式、化学式、表等があります▼ 〔式中、R^1、R^2、X、Yおよびnは前記と同じ
意味を表わす。〕 で示されるカルバモイルトリアゾール誘導体の製造法。 (8)一般式 ▲数式、化学式、表等があります▼ 〔式中、R^1およびR^2は同一または相異なり、低
級アルキル基、低級アルケニル基またはR^1とR^2
とで環をなす低級アルキレン基を表わし、XおよびYは
同一または相異なり、水素原子、ハロゲン原子、低級ア
ルキル基、低級アルコキシ基、低級アルコキシカルボニ
ル基、ニトロ基、アミノ基、アシルアミノ基またはトリ
フルオロメチル基を表わす。但し、R^1とR^2とが
共にメチル基であるものは除く。〕 で示されるカルバモイルトリアゾール誘導体を酸化する
ことを特徴とする一般式 ▲数式、化学式、表等があります▼ 〔式中、R^1、R^2、XおよびYは前記と同じ意味
を表わし、nは1または2を表わす。〕で示されるカル
バモイルトリアゾール誘導体の製造法。 (4)一般式 ▲数式、化学式、表等があります▼ 〔式中、R^1およびR^2は同一または相異なり、低
級アルキル基、低級アルケニル基またはR^1とR^2
とで環をなす低級アルキレン基を表わし、XおよびYは
同一または相異なり、水素原子、ハロゲン原子、低級ア
ルキル基、低級アルコキシ基、低級アルコキシカルボニ
ル基、ニトロ基、アミノ基、アシルアミノ基またはトリ
フルオロメチル基を表わし、nは0、1または2の整数
を表わす。但し、R^1とR^2とが共にメチル基であ
るものは除く。〕 で示されるカルバモイルトリアゾール誘導体を有効成分
として含有することを特徴とする除草剤。[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 and R^2 are the same or different, and are lower alkyl group, lower alkenyl group, or R^1 Represents a lower alkylene group forming a ring with R^2, X and Y are the same or different, hydrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower alkoxycarbonyl group, nitro group, amino group, acylamino group or represents a trifluoromethyl group, n is 0, 1
or represents an integer of 2. However, those in which R^1 and R^2 are both methyl groups are excluded. ] A carbamoyltriazole derivative represented by (2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X and Y are the same or different, hydrogen atom,
It represents a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group, a nitro group, an amino group, an acylamino group or a trifluoromethyl group, and n represents 0, 1 or 2. ] There are triazole derivatives represented by the general formula ▲ mathematical formulas, chemical formulas, tables, etc. 2
represents a lower alkylene group forming a ring, and Z represents a halogen atom. However, those in which R^1 and R^2 are both methyl groups are excluded. ] A general formula characterized by reacting with a carbamoyl halide represented by ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1, R^2, X, Y and n have the same meanings as above. represent. ] A method for producing a carbamoyltriazole derivative shown in the following. (8) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 and R^2 are the same or different, lower alkyl group, lower alkenyl group, or R^1 and R^2
represents a lower alkylene group forming a ring with Represents a methyl group. However, those in which R^1 and R^2 are both methyl groups are excluded. ] A general formula characterized by oxidizing a carbamoyltriazole derivative represented by ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1, R^2, X and Y represent the same meanings as above, n represents 1 or 2. ] A method for producing a carbamoyltriazole derivative. (4) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 and R^2 are the same or different, lower alkyl group, lower alkenyl group, or R^1 and R^2
represents a lower alkylene group forming a ring with It represents a methyl group, and n represents an integer of 0, 1 or 2. However, those in which R^1 and R^2 are both methyl groups are excluded. ] A herbicide characterized by containing a carbamoyltriazole derivative represented by the following as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP27958487A JP2503547B2 (en) | 1987-11-04 | 1987-11-04 | Carbamoyltriazole derivative, its production method and herbicide containing it as an active ingredient |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP27958487A JP2503547B2 (en) | 1987-11-04 | 1987-11-04 | Carbamoyltriazole derivative, its production method and herbicide containing it as an active ingredient |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH01121279A true JPH01121279A (en) | 1989-05-12 |
JP2503547B2 JP2503547B2 (en) | 1996-06-05 |
Family
ID=17613019
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP27958487A Expired - Lifetime JP2503547B2 (en) | 1987-11-04 | 1987-11-04 | Carbamoyltriazole derivative, its production method and herbicide containing it as an active ingredient |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2503547B2 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH021481A (en) * | 1988-03-07 | 1990-01-05 | Chugai Pharmaceut Co Ltd | Novel triazole compound and production thereof |
JPH02233665A (en) * | 1988-03-07 | 1990-09-17 | Chugai Pharmaceut Co Ltd | Novel triazole-based compound and production thereof |
WO1992002512A1 (en) * | 1990-08-03 | 1992-02-20 | Chugai Seiyaku Kabushiki Kaisha | Triazole compound |
EP0718291A1 (en) * | 1994-12-22 | 1996-06-26 | Chugai Seiyaku Kabushiki Kaisha | Method for the preparation of triazole compounds |
WO2019045085A1 (en) * | 2017-08-31 | 2019-03-07 | 北興化学工業株式会社 | 1-(n,n-disubstituted carbamoyl) 4-(substituted sulfonyl)triazolin-5-one derivatives, 4-(n,n-disubstituted carbamoyl) 1-(substituted sulfonyl)triazolin-5-one derivatives, and herbicide containing same as active ingredient |
-
1987
- 1987-11-04 JP JP27958487A patent/JP2503547B2/en not_active Expired - Lifetime
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH021481A (en) * | 1988-03-07 | 1990-01-05 | Chugai Pharmaceut Co Ltd | Novel triazole compound and production thereof |
JPH02233665A (en) * | 1988-03-07 | 1990-09-17 | Chugai Pharmaceut Co Ltd | Novel triazole-based compound and production thereof |
JPH0573745B2 (en) * | 1988-03-07 | 1993-10-15 | Chugai Pharmaceutical Co Ltd | |
WO1992002512A1 (en) * | 1990-08-03 | 1992-02-20 | Chugai Seiyaku Kabushiki Kaisha | Triazole compound |
EP0541809A1 (en) * | 1990-08-03 | 1993-05-19 | Chugai Seiyaku Kabushiki Kaisha | Triazole compound |
US5338720A (en) * | 1990-08-03 | 1994-08-16 | Chugai Seiyaku Kabushiki Kaisha | Triazole compounds and herbicidal compositions |
EP0541809B1 (en) * | 1990-08-03 | 1998-11-04 | Chugai Seiyaku Kabushiki Kaisha | Triazole compound |
EP0718291A1 (en) * | 1994-12-22 | 1996-06-26 | Chugai Seiyaku Kabushiki Kaisha | Method for the preparation of triazole compounds |
WO2019045085A1 (en) * | 2017-08-31 | 2019-03-07 | 北興化学工業株式会社 | 1-(n,n-disubstituted carbamoyl) 4-(substituted sulfonyl)triazolin-5-one derivatives, 4-(n,n-disubstituted carbamoyl) 1-(substituted sulfonyl)triazolin-5-one derivatives, and herbicide containing same as active ingredient |
JPWO2019045085A1 (en) * | 2017-08-31 | 2020-12-17 | 北興化学工業株式会社 | 1- (N, N-disubstituted carbamoyl) 4- (substituted sulfonyl) triazoline-5-one derivative, 4- (N, N-di substituted carbamoyl) 1- (substituted sulfonyl) triazoline-5-one derivative, and theirs Herbicide containing as an active ingredient |
US11076595B2 (en) | 2017-08-31 | 2021-08-03 | Hokko Chemical Industry Co., Ltd. | 1-(n,n-disubstituted carbamoyl) 4-(substituted sulfonyl)triazolin-5-one derivative, 4-(n,n-disubstituted carbamoyl) 1-(substituted sulfonyl)triazolin-5-one derivative, and herbicide containing said derivative as active ingredient |
Also Published As
Publication number | Publication date |
---|---|
JP2503547B2 (en) | 1996-06-05 |
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