JPH045282A - New 2-hydrazinobenzothiazole derivative and herbicide comprising the same derivative as active ingredient - Google Patents
New 2-hydrazinobenzothiazole derivative and herbicide comprising the same derivative as active ingredientInfo
- Publication number
- JPH045282A JPH045282A JP10536790A JP10536790A JPH045282A JP H045282 A JPH045282 A JP H045282A JP 10536790 A JP10536790 A JP 10536790A JP 10536790 A JP10536790 A JP 10536790A JP H045282 A JPH045282 A JP H045282A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- group
- alkyl group
- derivative
- hydrazinobenzothiazole
- 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 23
- 239000004009 herbicide Substances 0.000 title claims abstract description 18
- 239000004480 active ingredient Substances 0.000 title claims description 15
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 239000000126 substance Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 38
- -1 (substituted) pyridinyl Chemical group 0.000 abstract description 14
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- 229910052736 halogen Inorganic materials 0.000 abstract description 5
- 150000002367 halogens Chemical class 0.000 abstract description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 abstract description 2
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 abstract description 2
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- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical group O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 125000006003 dichloroethyl group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 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
- DWHOIYXAMUMQTI-UHFFFAOYSA-L disodium;2-[(1-sulfonatonaphthalen-2-yl)methyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC2=CC=CC=C2C(S(=O)(=O)[O-])=C1CC1=CC=C(C=CC=C2)C2=C1S([O-])(=O)=O DWHOIYXAMUMQTI-UHFFFAOYSA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical group O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 239000011419 magnesium lime Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LBUGCANJPIOMRJ-UHFFFAOYSA-N n'-methyl-n'-phenylacetohydrazide Chemical compound CC(=O)NN(C)C1=CC=CC=C1 LBUGCANJPIOMRJ-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- IXYACKYHUWCLAM-UHFFFAOYSA-M sodium;2-ethylhex-1-ene-1-sulfonate Chemical compound [Na+].CCCCC(CC)=CS([O-])(=O)=O IXYACKYHUWCLAM-UHFFFAOYSA-M 0.000 description 1
- FGDMJJQHQDFUCP-UHFFFAOYSA-M sodium;2-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(C(C)C)=CC=C21 FGDMJJQHQDFUCP-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
技術分野
本発明は文献未記載の新規な2−ヒドラジノベンゾチア
ゾール誘導体及びそれを有効成分として含有する除草剤
に関するものである。DETAILED DESCRIPTION OF THE INVENTION Technical Field The present invention relates to a novel 2-hydrazinobenzothiazole derivative, which has not been described in any literature, and a herbicide containing the same as an active ingredient.
従来の技術
特開昭48−72164号公報には、2−ヒドラジノベ
ンゾチアゾール誘導体についての合成例が示されている
が、それらの除草活性作用等について全く記載されてい
ない。Prior art JP-A-48-72164 discloses synthesis examples of 2-hydrazinobenzothiazole derivatives, but does not describe their herbicidal activity at all.
発明の構成
本発明者らは、上記公知のヒドラジノベンゾチアゾール
誘導体とは構造の異なる新規な2−ヒドラジノベンゾチ
アゾール誘導体を合成するとともに、それらが優れた除
草活性を有する化合物であることを見出し本発明に到達
した。Structure of the Invention The present inventors have synthesized novel 2-hydrazinobenzothiazole derivatives having a different structure from the above-mentioned known hydrazinobenzothiazole derivatives, and have discovered that they are compounds with excellent herbicidal activity. We have arrived at the present invention.
斯くして、本発明によれば、一般式(I)R′
[但し、R五は
水素原子、炭素数1〜6のアルキル基または炭素数2〜
6のアルカノイル基であり、R2及びR3は、それぞれ
独立して
炭素数1〜6のアルキル基、炭素数2〜4のアルケニル
基、炭素数3または4のアルキニル基、置換されてもよ
いアリール基または置換されてもよいピリジニル基であ
る。Thus, according to the present invention, the general formula (I)R' [where R5 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a
R2 and R3 are each independently an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 3 or 4 carbon atoms, or an optionally substituted aryl group. or an optionally substituted pyridinyl group.
R4、R6、R6及びR7は、それぞれ独立して水素原
子、ハロゲン原子、炭素数1〜6のアルキル基、炭素数
1〜6のハロアルキル基または炭素数I〜6のアルコキ
シ基である]で表わされる2−ヒドラジノベンゾチアゾ
ール誘導体か提供される。R4, R6, R6 and R7 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. 2-hydrazinobenzothiazole derivatives are provided.
更に、本発明によれは、上記式(I)化合物を有効成分
として含有することを特徴とする除草剤か提供される。Furthermore, the present invention provides a herbicide characterized by containing the above compound of formula (I) as an active ingredient.
発明の効果
本発明の上記式(I)で表わされる2−ヒドラジノベン
ゾチアゾール誘導体は、本発明者の知る限り文献未記載
の新規な化合物である。本発明の上記式(I)で表わさ
れる2−ヒドラジノベンゾチアゾール誘導体は、ベンゾ
チアゾール環の2位に、2置換あるいは3置換のヒドラ
ジノ基を有することが特徴であり、その構造的特徴によ
ってこの式(I)の2−ヒドラジノベンゾチアゾール誘
導体は除草剤として優れた生理活性が発揮されるものと
考えられる。Effects of the Invention The 2-hydrazinobenzothiazole derivative represented by the above formula (I) of the present invention is a novel compound that has not been described in any literature as far as the inventors know. The 2-hydrazinobenzothiazole derivative of the present invention represented by the above formula (I) is characterized by having a di- or tri-substituted hydrazino group at the 2-position of the benzothiazole ring, and due to its structural characteristics, this It is believed that the 2-hydrazinobenzothiazole derivative of formula (I) exhibits excellent physiological activity as a herbicide.
本発明の除草剤は、殺草スペクトラムが広く、その上通
常の除草剤に比較して極めて少ない使用量でその除草活
性を充分発揮するという優れた特性を有する除草剤であ
る。The herbicide of the present invention has a wide herbicidal spectrum and has the excellent property of fully exhibiting its herbicidal activity with an extremely small amount of use compared to ordinary herbicides.
発明の詳細な説明
次に本発明の前記一般式(I)で表わされる2ヒドラジ
ノベンゾチアゾ一ル誘導体についてさらに詳細に説明す
る。Detailed Description of the Invention Next, the 2hydrazinobenzothiazol derivative represented by the general formula (I) of the present invention will be described in more detail.
前記一般式(I)中のヒドラジノ基においてR1として
は
(1)水素原子の他に、(u)炭素数1〜6のアルキル
基としては、例えばメチル、エチル、nプロピル、1s
o−プロピル、n−ブチル、1so−ブチル、5ec−
ブチル、ter−ブチノペペンチル及びその構造異性体
等が挙げられ、これらのうち炭素数1〜3のアルキル基
が好ましく、さらに(ii)炭素数2〜6のアルカノイ
ル基としては例えば、アセチル、プロピオニル、ブチリ
ル、インブチリル、バレリル、インバレリル、ヘキサノ
イル及びその構造異性体が挙げられ、これらのうち炭素
数2〜3のアルカノイル基が好ましい。R1としては上
記(1)〜(ii)中、(1)水素原子が特に好ましい
。In the hydrazino group in the general formula (I), R1 includes (1) a hydrogen atom, and (u) an alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, 1s
o-propyl, n-butyl, 1so-butyl, 5ec-
Examples include butyl, ter-butynopopentyl, structural isomers thereof, and among these, alkyl groups having 1 to 3 carbon atoms are preferred, and (ii) alkanoyl groups having 2 to 6 carbon atoms include, for example, acetyl, propionyl, butyryl. , imbutyryl, valeryl, invaleryl, hexanoyl and structural isomers thereof, and among these, an alkanoyl group having 2 to 3 carbon atoms is preferred. Among the above (1) to (ii), (1) hydrogen atom is particularly preferred as R1.
R2及びR3としては同一もしくは異なり、(i)炭素
数1〜6のアルキル基としては、例えはメチル、エチル
、n−プロピル、ls○−プロピル、n−ブチル、1s
o−ブチル、5ee−ブチル、ter−ブチル、ペンチ
ル及びその構造異性体等が挙げられ、これらのうち炭素
数1〜3のアルキル基が好ましく、
(u〕炭素数2〜4のアルケニル基としては、例えばビ
ニル、アリルまたはインブテニル等が示され、
(ii)炭素数3または4のアルキニル基としては、例
えばグロパルギルまたはブチニル等が示され、
(iv )置換されてもよいアリール基におけるアリー
ルとしては、フェニル基、ナフチル基またはビフェニル
基、好ましくはフェニル基が挙げられ、これらは1〜5
個、好ましくは1〜3個の置換基を有していてもよく、
その置換基としては、炭素数I〜4のアルキル基、炭素
数1〜4のアルコキシ基、ハロゲンまたはトリフルオロ
メチル基等が示され、具体例としては、フェニル、3−
トリフルオロメチルフェニルまたは3.4−ジクロロフ
ェニル等か挙げられ、
(v)置換されてもよいピリジニル基としてはこれらは
1〜5個、好ましくは1〜3個の置換基を有していても
よく、その置換基としては、炭素数I〜4のアルキル基
、炭素数1〜4のアルコキシ基、ハロゲンまたはトリフ
ルオロメチル基等が示される。R2 and R3 are the same or different, and (i) the alkyl group having 1 to 6 carbon atoms includes, for example, methyl, ethyl, n-propyl, ls○-propyl, n-butyl, 1s
Examples include o-butyl, 5ee-butyl, ter-butyl, pentyl, and structural isomers thereof, and among these, alkyl groups having 1 to 3 carbon atoms are preferable, and (u) alkenyl groups having 2 to 4 carbon atoms are , for example, vinyl, allyl or imbutenyl; (ii) an alkynyl group having 3 or 4 carbon atoms, such as glopargyl or butynyl; (iv) an optionally substituted aryl group; Phenyl group, naphthyl group or biphenyl group, preferably phenyl group, which has 1 to 5
, preferably 1 to 3 substituents,
Examples of the substituent include an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen or a trifluoromethyl group, and specific examples include phenyl, 3-
Examples include trifluoromethylphenyl or 3,4-dichlorophenyl, and (v) the optionally substituted pyridinyl group may have 1 to 5, preferably 1 to 3 substituents. Examples of the substituent include an alkyl group having I to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen or a trifluoromethyl group.
R4R5、R6及びR7としては互いに同一もしくは異
なり、
(1)水素原子の他に、(u)ハロゲン原子としては弗
素、塩素、臭素または沃素であり、これらのうち弗素ま
たは塩素が好ましい。(ij)炭素数1〜6のアルキル
基としては、例えばメチル、エチル、n−7’口ピル、
1so−プロピル、n−ブチル、1so−ブチル、5e
c−ブチル、ter−ブチル、ペンチル及びその構造異
性体等が挙げられ、これらのうち炭素数1〜3のアルキ
ル基が好ましく、(iv )炭素数1〜6のハロアルキ
ル基としては、1〜6個のハロゲン殊に弗素または塩素
で置換された上記(ii)のアルキル基が適当であり、
例えハクロロメチル、クロロエチル、ジクロロエチル、
ジフルオロメチル、トリフルオロメチルまたはトリフル
オロエチル等が挙げられ、これらのうちで1〜3個のハ
ロゲンを有する炭素数1〜3のアルキル基か好ましく、
(v)炭素数1〜6のアルコキシ基としては、例えば、
メトキシ、エトキシ、プロポキン、インプロポキシ、ブ
トキシまたはインブトキシ、ter−ブトキシ等が挙げ
られ、これらのうち炭素数1〜3のアルコキシ基が好ま
しい。R4R5, R6 and R7 are the same or different, and in addition to (1) a hydrogen atom, (u) a halogen atom is fluorine, chlorine, bromine or iodine, and among these, fluorine or chlorine is preferred. (ij) Examples of the alkyl group having 1 to 6 carbon atoms include methyl, ethyl, n-7′,
1so-propyl, n-butyl, 1so-butyl, 5e
Examples include c-butyl, ter-butyl, pentyl and structural isomers thereof, and among these, alkyl groups having 1 to 3 carbon atoms are preferable, and (iv) haloalkyl groups having 1 to 6 carbon atoms include 1 to 6 carbon atoms. Suitable are the alkyl groups of (ii) above substituted with halogens, especially fluorine or chlorine;
For example, hachloromethyl, chloroethyl, dichloroethyl,
Examples include difluoromethyl, trifluoromethyl, trifluoroethyl, etc., and among these, an alkyl group having 1 to 3 carbon atoms and having 1 to 3 halogens is preferable.
(v) As the alkoxy group having 1 to 6 carbon atoms, for example,
Examples include methoxy, ethoxy, propoquine, impropoxy, butoxy or imbutoxy, ter-butoxy, and among these, an alkoxy group having 1 to 3 carbon atoms is preferred.
本発明における前記一般式(1)は如何なる製造法によ
って得られたものであってもよい。また前記一般式(1
)は農薬的に許容しうる酸との塩を形成していても差支
えない。The general formula (1) in the present invention may be obtained by any manufacturing method. Also, the general formula (1
) may form a salt with an agriculturally acceptable acid.
前記一般式(I)は、例えば下記に示す方法によって製
造することができるが、本発明はこの方法によって製造
されたものに限定を受けるわけではない。The general formula (I) can be produced, for example, by the method shown below, but the present invention is not limited to products produced by this method.
R′
(II) (II[)
R′
CI)
[式中、RI R2R3R4R5R6及びR7は前記
一般式(I)における定義と同しである。Acはアセチ
ル基を表わす。]上記反応式に示したように、クロロベ
ン7’−)アゾール(I[)とアセチルヒドラジン(I
[[)を例えば有機溶媒中あるいは無溶媒中、塩基の存
在下で反応させることにより本発明の一般式(I)の化
合物を製造することができる。R' (II) (II[) R' CI) [Wherein, RI R2R3R4R5R6 and R7 are as defined in the general formula (I) above. Ac represents an acetyl group. ] As shown in the above reaction formula, chloroben7'-)azole (I[) and acetylhydrazine (I
The compound of general formula (I) of the present invention can be produced by reacting [[) in an organic solvent or in the absence of a solvent in the presence of a base.
反応は化合物(n)に対して塩基を1〜3モル当量、好
ましくは1−1.5モル当量用いてO′cあるいは室温
で1ないし5時間行われる。塩基としては、例えば水酸
化ナトリウム、水酸化カリウム、水素化ナトリウムまた
は水素化カリウム等が挙げられる。The reaction is carried out using 1 to 3 molar equivalents, preferably 1 to 1.5 molar equivalents, of a base based on compound (n) at O'c or room temperature for 1 to 5 hours. Examples of the base include sodium hydroxide, potassium hydroxide, sodium hydride, and potassium hydride.
反応終了後は、反応混合物を水中にあけ有機溶媒で抽出
、再結晶、カラムクロマト等の常法の手段に従って処理
することにより、本発明の目的とする化合物を単離する
ことができる。After completion of the reaction, the target compound of the present invention can be isolated by pouring the reaction mixture into water and treating it according to conventional methods such as extraction with an organic solvent, recrystallization, and column chromatography.
次に実施例により本発明を更に具体的に説明する。Next, the present invention will be explained in more detail with reference to Examples.
実施例
ジエチルエーテルで抽出し無水硫酸マグネシウムで乾燥
した。カラムクロマト[溶離液:酢酸エチル/ヘキサン
=115(容積比)jで精製し、2.2g(収率74%
)のニーメチル−1−7エニルー2−(2−ベンゾチア
ゾリル)ヒドラジンを得た。Example Extracted with diethyl ether and dried over anhydrous magnesium sulfate. Purified by column chromatography [eluent: ethyl acetate/hexane = 115 (volume ratio)], 2.2 g (yield 74%)
) was obtained as methyl-1-7enyl-2-(2-benzothiazolyl)hydrazine.
上述の実施例と同様な方法で、下記表1に示す本発明の
化合物を合成した。結果をまとめて表1に示す。また表
2に得られた化合物のN、M、R分析値を示す。Compounds of the present invention shown in Table 1 below were synthesized in the same manner as in the above examples. The results are summarized in Table 1. Further, Table 2 shows the N, M, and R analysis values of the obtained compound.
1.64g(0,01モル)の1−アセチル−2−メチ
ル−2−フェニルヒドラジンをDMF 50dに溶かし
、0℃で水素化ナトリウム0.48g(0,01モル)
を加えた。次に1.69g(0゜01モル)の2−クロ
ロベンゾチアゾールを0℃で加え室温で2時間撹拌した
。反応液を水にあけ本発明の上記式(I)で表わされる
化合物は、殺草活性が著しく高いので、少量の使用で極
めて優れた殺草活性を示すとともに、栽培作物に対して
高い安全性を有しており、農業上有用な除草剤となり得
る。1.64 g (0.01 mol) of 1-acetyl-2-methyl-2-phenylhydrazine are dissolved in DMF 50d and 0.48 g (0.01 mol) of sodium hydride are dissolved at 0°C.
added. Next, 1.69 g (0°01 mol) of 2-chlorobenzothiazole was added at 0° C. and stirred at room temperature for 2 hours. The reaction solution is poured into water, and the compound represented by the above formula (I) of the present invention has extremely high herbicidal activity, so it shows extremely excellent herbicidal activity even when used in a small amount, and is highly safe for cultivated crops. It can be a useful herbicide in agriculture.
本発明の化合物は、水田及び畑地に生育する発生前から
生育期までの諸雑草を有効に防除できる。The compounds of the present invention can effectively control various weeds growing in paddy fields and fields from the pre-emergence stage to the growing season.
例えば、水田に発生するノヒエ、タマカヤツリ、コナギ
、アゼナ、キカシグサ、ホタルイ等の一年性雑草及びマ
ツバイ、ウリカワ、ミズガヤツリ、クログワイ等の多年
性雑草を防除することかできる。また、畑地に発生する
ヒエ、メヒシバ、オヒシバ、エノコログサ、スズメノテ
ツボウ、ノhコベ、タデ類、ヒエ類、イチビ、シロザ、
アメリカキンコジカ、オナモミ、ブタフサ、ナズナ、り
不ツケバナ、センダングサ、ヤエムグラ、ソバカズラ等
の一年生雑草のみならずハスマゲ、ヒルガオ、ジョンソ
ングラス、シバムギ等の多年性雑草も防除することがで
きる。特に本発明の化合物は、畑地に生育する一年生広
集雑草にも強い雑草活性を示し、例えば、アオビユ、ス
ベリヒュ、オナモミ、センダングサ、アレチウリ、コア
カザ、サナエタデ、オオイヌタデ、ハコベ、ナズナ、ミ
ミナグサ、マルパアサガオ、イヌホウズキ、ワルナスビ
、オオバコ、イチビ、カタバミ、ヤエムグラ等の雑草を
有効に防除できる。For example, it is possible to control annual weeds that occur in paddy fields, such as Japanese grasshopper, Japanese cypress, Japanese cypress, Japanese azalea, Japanese cypress, and Japanese firefly, as well as perennial weeds such as Japanese grasshopper, Japanese cypress, Japanese cypress, and black snail. In addition, barnyard grass, Japanese grasshopper, Japanese grasshopper, foxtail grass, sparrow gnome, Japanese barnyard grass, knotweed, Japanese barnyard grass, Japanese barnyard grass, Japanese barnyard grass, etc., which occur in fields.
It is possible to control not only annual weeds such as American goldenrod, Japanese fir, pigweed, shepherd's purse, shepherd's lily, meadowweed, commonweed, and buckwheat, but also perennial weeds such as spiny grass, bindweed, johnson grass, and grasshopper. In particular, the compound of the present invention exhibits strong weed activity against annual widespread weeds that grow in fields, such as blueberry, purslane, Japanese fir, Japanese lily, Japanese chinensis, Japanese knotweed, Japanese knotweed, Japanese knotweed, Japanese knotweed, chickweed, shepherd's shepherd's purse, commonweed, Marpa morning glory, etc. It can effectively control weeds such as oxalis, oxalis, plantain, and other weeds.
更に、本発明の化合物は水田、畑地のみならず、果樹園
、桑園等の農耕地及び芝生、畦畔等の非農耕地に発生す
る一年性及び多年性雑草を有効に防除することができる
。Furthermore, the compounds of the present invention can effectively control annual and perennial weeds that occur not only in rice fields and fields, but also in agricultural lands such as orchards and mulberry gardens, and in non-agricultural lands such as lawns and ridges. .
しかも、本発明の化合物は、栽培作物に対して高い安全
性を有しており、特にイネ、トウモロコシ、クヌギ、オ
オムギ等の有用禾本科作物及びダイズ、ワタ等の有用広
葉作物の生育に実用上問題となる程度の薬害を与えない
。Moreover, the compound of the present invention has high safety against cultivated crops, and is particularly useful for growing useful legumes such as rice, corn, oak, barley, and useful broad-leaved crops such as soybean and cotton. Does not cause drug damage to the extent that it becomes a problem.
本発明の化合物(1)を除草剤として用いる場合には、
担体もしくは希釈剤、添加剤及び補助剤等とそれ自体公
知の手法で混合して、通常農薬として用いられる製剤形
態、例えば粉剤、粒剤、水和剤、乳剤、水溶剤、フロア
ブル剤等に調製して使用される。また他の農薬、例えば
殺菌剤、殺虫剤、殺ダニ剤、他の除草剤、植物生長調節
剤等、肥料及び土壌改良剤等と混合又は併用して使用す
ることができる。When using the compound (1) of the present invention as a herbicide,
Mix with carriers or diluents, additives, auxiliaries, etc. by methods known per se to prepare formulations commonly used as agricultural chemicals, such as powders, granules, wettable powders, emulsions, water-solvents, flowables, etc. used. It can also be mixed or used in combination with other agricultural chemicals, such as fungicides, insecticides, acaricides, other herbicides, plant growth regulators, fertilizers, soil conditioners, and the like.
特に他の除草剤と混合使用することにより、使用薬量を
減少させ、また省力化をもたらすのみならず、両薬剤の
共力作用による殺草スペクトラムの拡大及び相乗作用に
よる一層高い効果も期待できる。In particular, when used in combination with other herbicides, it is possible to not only reduce the amount of chemicals used and save labor, but also to expand the herbicidal spectrum due to the synergistic action of both herbicides, and to achieve even higher effects due to the synergistic action. .
製剤に際して用いられる担体若しくは希釈剤としては、
一般に使用される固体ないしは液体の担体が挙げられる
。Carriers or diluents used in formulation include:
Commonly used solid or liquid carriers may be used.
固体担体としては、例えば、カオリナイト群、モンモリ
ロナイト群あるいはアバタルジャイト群等で代表される
クレー類やタルク、雲母、ロウ石、軽石、バーミキュラ
イト、石膏、炭酸カルシウム、ドロマイト、けいそう土
、マグネシウム石灰、りん灰石、ゼオライト、無水ケイ
酸、合成ケイ酸カルシウム等の無機物質;大豆粉、タバ
コ粉、クルミ粉、小麦粉、木粉、でんぷん、結晶セルロ
ース等の植物性有機物質;クマロン樹脂、石油樹脂、ア
ルキッド樹脂、ポリ塩化ビニル、ポリアルキレングリコ
ール、ケトン樹脂、エステルガム、コーパルカム、タン
マルガム等の合成又は天然の高分子化合物;カルナバロ
ウ、蜜ロウ等のワックス類あるいは尿素等が例示できる
。Examples of solid carriers include clays such as kaolinite group, montmorillonite group, or abatalgite group, talc, mica, waxite, pumice, vermiculite, gypsum, calcium carbonate, dolomite, diatomaceous earth, and magnesium lime. , apatite, zeolite, silicic anhydride, synthetic calcium silicate, and other inorganic substances; soybean powder, tobacco powder, walnut powder, wheat flour, wood flour, starch, crystalline cellulose, and other organic plant substances; coumaron resin, petroleum resin , alkyd resins, polyvinyl chloride, polyalkylene glycols, ketone resins, ester gums, copalcum, tanmal gum, and other synthetic or natural polymeric compounds; waxes such as carnauba wax and beeswax, and urea.
適当な液体担体としては、例えば、ケロシン、鉱油、ス
ピンドル油、ホワイトオイル等のパラフィン系又はナフ
テン系炭化水素:トルエン、キシレン、エチルベンゼン
、クメン、メチルナフタリン等の芳香族炭化水素二ジオ
キサン、テトラヒドロ7ランのようなエーテル類;アセ
トン、メチルエチルケトン、ジイソブチルケトン、シク
ロヘキサノン、アセトフェノン、イソホロン等のケトン
類;酢酸エチル、酢酸アミル、エチレングリコールアセ
テート、ジエチレングリコールアセテート、マレイン酸
ジブチル、コハク酸ジエチル等のエステル等;メタノー
ル、n−ヘキサノール、エチレングリコール、ジエチレ
ングリコール、シクロヘキサノール、ベンジルアルコー
ル等のアルコール類;エチレングリコールユチルユーテ
ル、エチレングリコールフェニルエーテノ呟 ジエチレ
ングリコールエチルエーテル、ジエチレングリコールブ
チルエーテル等のエーテルアルコール類;ジメチルホル
ムアミド、ジメチルスルホキシド等の極性溶媒あるいは
水等が挙げられる。Suitable liquid carriers include, for example, paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil, white oil; aromatic hydrocarbons such as toluene, xylene, ethylbenzene, cumene, methylnaphthalene; didioxane, tetrahydro7rane; ethers such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, isophorone; esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate, diethyl succinate; methanol, Alcohols such as n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol, benzyl alcohol; ether alcohols such as ethylene glycol ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether, diethylene glycol butyl ether; dimethyl formamide, dimethyl sulfoxide, etc. Examples include polar solvents and water.
その他に本発明の化合物の乳化、分散、湿潤、展着、拡
展、結合、崩壊性調節、有効成分安定化、流動性改良、
防錆、凍結防止等の目的で界面活性剤その他の補助剤を
使用することもできる。In addition, emulsification, dispersion, wetting, spreading, spreading, binding, disintegration adjustment, active ingredient stabilization, flowability improvement, etc. of the compound of the present invention,
Surfactants and other auxiliary agents may also be used for purposes such as rust prevention and anti-freezing.
使用される界面活性剤の例としては、非イオン性、陰イ
オン性、陽イオン性及び両性イオン性のいずれの物も使
用しうるが、通常は非イオン性及び(又は)陰イオン性
の物が使用される。適当な非イオン性界面活性剤として
は、例えばラウリルアルコール、ステアリルアルコール
、オレイルアルコール等の高級アルコールにエチレンオ
キシドを重合付加させた化合物:イソオクチルフェノル
、ノニルフェノール等のアルキルフェノールにエチレン
オキシドを重合付加させた化合物;ブチルナフトール、
オクチルナフトール等のアルキルナフトールにエチレン
オキシドを重合付加させt;化合物;パルミチン酸、ス
テアリン酸、オレイン酸等の高級脂肪酸にエチレンオキ
シドを重合付加させた化合物;ソルビタン等の多価アル
コールの高級脂肪族エステル及びそれにエチレンオキシ
ドを重合付加させた化合物:エチレンオキシドとプロピ
レンオキシドをブロック重合付加させた化合物等が挙げ
られる。Examples of surfactants that can be used include nonionic, anionic, cationic, and zwitterionic surfactants, but usually nonionic and/or anionic surfactants are used. is used. Suitable nonionic surfactants include, for example, compounds in which ethylene oxide is polymerized and added to higher alcohols such as lauryl alcohol, stearyl alcohol, and oleyl alcohol; and compounds in which ethylene oxide is polymerized and added to alkylphenols such as isooctylphenol and nonylphenol. ;Butylnaphthol,
Compounds obtained by polymerizing and adding ethylene oxide to alkylnaphthols such as octylnaphthol; Compounds obtained by polymerizing and adding ethylene oxide to higher fatty acids such as palmitic acid, stearic acid, and oleic acid; Higher aliphatic esters of polyhydric alcohols such as sorbitan; Compounds obtained by polymerization addition of ethylene oxide: Compounds obtained by block polymerization addition of ethylene oxide and propylene oxide, etc. may be mentioned.
適当な陰イオン性界面活性剤としては、例えば、ラウリ
ル硫酸ナトリウム、オレイルアルコール硫酸エステルア
ミン塩等のアルキル硫酸エステル塩;スルホこはく酸ジ
オクチルエステルナトリウム、2−エチルヘキセンスル
ホン酸ナトリウム等のアルキルスルホン酸塩;イソプロ
ピルナフタレンスルホン酸ナトリウム、メチレンビスナ
フタレンスルホン酸ナトリウム、リグニンスルホン酸ナ
トリウム、ドデシルベンゼンスルホン酸ナトリウム等の
アリールスルホン酸塩等が挙げられる。Suitable anionic surfactants include, for example, alkyl sulfate salts such as sodium lauryl sulfate and oleyl alcohol sulfate amine salt; alkyl sulfonate salts such as sodium sulfosuccinate dioctyl ester and sodium 2-ethylhexene sulfonate. arylsulfonates such as sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, sodium ligninsulfonate, and sodium dodecylbenzenesulfonate;
更に、本発明の除草剤は、製剤の性状を改善し除草効果
を高める目的で、カゼイン、ゼラチン、アルブミン、ニ
カワ、アルギン酸ソーダ、カルボキシメチルセルロース
、メチルセルロース、ヒドロキシエチルセルロース、ポ
リビニルアルコール等の高分子化合物や他の補助剤を併
用することもできる。Furthermore, the herbicide of the present invention may contain polymeric compounds such as casein, gelatin, albumin, glue, sodium alginate, carboxymethylcellulose, methylcellulose, hydroxyethylcellulose, polyvinyl alcohol, etc., for the purpose of improving the properties of the preparation and increasing the herbicidal effect. It is also possible to use adjuvants.
上記の担体及び種々の補助剤は製剤の剤型、適用場面等
を考慮して、目的に応じてそれぞれ単独あるいは組み合
わせて適宜使用される。The above-mentioned carriers and various auxiliary agents are used individually or in combination as appropriate depending on the purpose, taking into account the dosage form of the preparation, the application situation, etc.
このようにして得られた各種製剤形における本発明化合
物(Dの有効成分含有率は製剤形により種々変化するも
のであるが、通常0.1〜99重量%が適当であり、好
ましくは1〜80重量%が最も適当である。The active ingredient content of the compound of the present invention (D) in the various formulations thus obtained varies depending on the formulation, but is usually 0.1 to 99% by weight, preferably 1 to 99% by weight. 80% by weight is most suitable.
粉剤の場合は、例えば有効成分化合物を通常1〜25重
量%含有し、残部は固体担体及び界面活性剤等である。In the case of a powder, for example, the active ingredient compound is usually contained in an amount of 1 to 25% by weight, and the remainder is a solid carrier, a surfactant, and the like.
水利剤の場合は、例えば有効成分化合物を通常25〜9
0%含有し、残部は固体担体及び分散湿潤剤であって、
必要に応じて保護コロイド剤、消泡剤等か加えられる。In the case of irrigation agents, for example, the active ingredient compound is usually 25 to 9
0%, the remainder being a solid carrier and a dispersion wetting agent,
Protective colloids, antifoaming agents, etc. may be added as necessary.
粒剤の場合は、例えば有効成分化合物を通常1〜35重
量%含有し、残部は固体担体及び界面活性剤等である。In the case of granules, for example, the active ingredient compound is usually contained in an amount of 1 to 35% by weight, and the remainder is a solid carrier, a surfactant, and the like.
有効成分化合物は固体担体と均一に混合されているか、
あるいは固体担体の表面に均一に固着又は吸着されてお
り、粒の径は約0゜2ないし1.5+n+nである。Is the active ingredient compound homogeneously mixed with the solid carrier?
Alternatively, it is fixed or adsorbed uniformly on the surface of a solid carrier, and the particle diameter is about 0°2 to 1.5+n+n.
乳剤の場合は、例えば有効成分化合物を通常5〜30重
量%含有しており、これに約5ないし20重量%の乳化
剤が含まれ、残部は液体担体であり、必要に応じて展薯
剤及び防錆剤等が加えられる。In the case of an emulsion, for example, it usually contains 5 to 30% by weight of the active ingredient compound, this includes about 5 to 20% by weight of an emulsifier, and the remainder is a liquid carrier, and if necessary, a filler and an emulsifier. Rust inhibitors etc. are added.
フロアブル剤の場合は、例えば有効成分化合物を通常5
〜50重量%含有しており、これに3ないし10重量%
の分散湿潤剤が含まれ、残部は水であり必要に応じて保
護コロイド剤、防腐剤、消泡剤等が加えられる。In the case of flowable agents, for example, the active ingredient compound is usually
~50% by weight, in addition to 3 to 10% by weight
The remainder is water, and a protective colloid, a preservative, an antifoaming agent, etc. are added as necessary.
本発明の2−ヒドラジノベンゾチアゾール誘導体は、一
般式(1)の化合物のまま、あるいは上述した様な任意
の製剤形態で除草剤として使用することができる。The 2-hydrazinobenzothiazole derivative of the present invention can be used as a herbicide as a compound of general formula (1) or in any formulation form as described above.
本発明の除草剤は、水田および畑地に生育する発生前か
ら生育期までの諸雑草に施用できる。その施用量は一般
式(I)で表される化合物量(有効成分量)としてlh
a当り、0.05−5kg程度、好ましくは0.1〜1
kg程度であり、目的とする雑草の種類、生育段階、
施用場所、施用時期、天候等によって適宜に選択変更で
きる。The herbicide of the present invention can be applied to various weeds growing in rice fields and fields from the pre-emergence stage to the growing season. The application amount is lh as the amount of the compound (active ingredient amount) represented by the general formula (I).
Approximately 0.05-5 kg per a, preferably 0.1-1
kg, and the target weed type, growth stage,
The selection can be changed as appropriate depending on the application location, application time, weather, etc.
次に、本発明の化合物を用いた製剤例の数態様を示す。Next, several embodiments of formulation examples using the compounds of the present invention will be shown.
なお、下記製剤例中の「部」は重量基準である。Note that "parts" in the following formulation examples are based on weight.
製剤例1(粒剤)
化合物N〜2 5部ベン
トナイト 50部タルク
40部ドデシルベ
ンゼンスルホン酸ソーダ 2部リグニンスルホン
酸ソーダ 2部以上を充分に混合した
後、適量の水を加えて混練し、造粒機を用いて造粒して
粒剤100部を得製剤例4(フロアブル剤)
た。Formulation example 1 (granules) Compound N~2 5 parts bentonite 50 parts talc
40 parts Sodium dodecylbenzenesulfonate 2 parts Sodium ligninsulfonate After thoroughly mixing 2 parts or more, add an appropriate amount of water, knead, and granulate using a granulator to obtain 100 parts of granules. Formulation Example 4 (Flowable agent).
製剤例2(水利剤)
化合物Nへ9 20部ケイ
ソウ土 63部ホワイトカ
ーボン 15部ドデシルベンゼ
ンスルホン酸ソーダ 2部以上を混合し、ニーダ
−で均一に混合粉砕して水和剤100部を得た。Formulation Example 2 (Irrigation agent) Compound N9 20 parts diatomaceous earth 63 parts white carbon 15 parts Sodium dodecylbenzenesulfonate 2 parts or more were mixed and uniformly mixed and ground in a kneader to obtain 100 parts of a wettable powder. .
製剤例3(乳剤)
化合物隘4 30部キシレン
55部シクロへキサノ
ン 10部ドデシルベンゼンス
ルホン酸カルシウム 3部ポリオキシエチレンアルキ
ルアリールエーテル
2部以上を均一に混合溶解して乳剤100部を得た。Formulation example 3 (emulsion) Compound number 4 30 parts xylene 55 parts cyclohexanone 10 parts calcium dodecylbenzenesulfonate 3 parts polyoxyethylene alkylaryl ether
Two or more parts were uniformly mixed and dissolved to obtain 100 parts of an emulsion.
化合物NC,,9
30部
ドデンルベンゼンスルホン酸カルシウム 2部消泡剤
1部プロピレング
リコール 5部水
59部以上を
湿式ボールミルで均一に粉砕混合し、フロアブル剤10
0部を得た。Compound NC,,9 30 parts calcium dodenlebenzenesulfonate 2 parts antifoaming agent 1 part propylene glycol 5 parts water
59 parts or more were uniformly ground and mixed in a wet ball mill to form a flowable agent of 10 parts.
I got 0 copies.
上述の製剤例に準じて本発明の化合物を用いた除草剤が
それぞれ製剤できる。Herbicides using the compounds of the present invention can be formulated according to the formulation examples described above.
次に、本発明除草剤の奏する効果を試験例を挙げて説明
する。Next, the effects of the herbicide of the present invention will be explained using test examples.
試験例1(水田土壌処理)
面積200co+”のプラスチックポットに適量の化成
肥料を混合した水田土壌を詰め、これに予め温室内で生
育させて2葉期に達した水稲(品種二日本晴)を2株(
2本1株)移植し、更にノビエ、アゼナ、コナギ、ホタ
ルイの種子を播種した。Test Example 1 (Paddy soil treatment) A plastic pot with an area of 200 co+" was filled with paddy soil mixed with an appropriate amount of chemical fertilizer, and 2 paddy rice (variety: Ni Nihonbare) that had been grown in a greenhouse and had reached the 2-leaf stage were placed in it. KK(
Two plants (one plant) were transplanted, and seeds of Japanese wildflower, Japanese azalea, Japanese cypress, and firefly were sown.
水稲移植及び播種3日後に、表2に示す各化合物を製剤
例2に準じて水和剤に調製し、有効成分で1 ha当り
0.2kg又は0 、5 kgとなるように適量の水で
希釈し、ピペットで滴下処理した。除草効果及び薬害程
度の調査は、薬剤処理25日後に下記の基準に従い行っ
た。Three days after transplanting and sowing rice, each compound shown in Table 2 was prepared into a wettable powder according to Formulation Example 2, and mixed with an appropriate amount of water so that the amount of active ingredient was 0.2 kg or 0.5 kg per 1 ha. It was diluted and added dropwise with a pipette. The herbicidal effect and the degree of chemical damage were investigated 25 days after the chemical treatment according to the following criteria.
その結果を表2に示す。The results are shown in Table 2.
除草効果 浅草率(無処理区に対する浅草率)10
0 〜 1%未満
9 1%以上〜 lO%//
8 10%/l〜 20%//
7 20%〃〜 30%//
6 30%〃〜 40%〃
5 40%〃〜 50%//
4 50%// 〜 60%/13 60
%// 〜 70%//2 70%〃〜 80%
//
l 80%/l〜 90%/10 90
%〃〜100%
薬害程度
:薬害なし
±:僅小害
十二小害
廿:中寄
+1+二大害
×:枯死
試験例2(水田生育期処理)
面積200cm”のプラスチックポットに適量の化成肥
料を混合した水田土壌を詰め、これに予め温室内で生育
させて2葉期に達した水稲(品種二日本晴)を2株(2
本1株)移植し、更にノヒエ、アゼナ、コナギ、ホタル
イの種子を播種した。水稲移植及び播種後10日間20
〜25°Cのガラス温室内で育成した後、表3に示す各
化合物を製剤例2に準じて水利剤に調整し、有効成分で
lha当りl kgとなるように適量の水で希釈し、ピ
ペットで滴下処理した。除草効果及び薬害程度の調査は
薬剤処理25日後に試験例1の基準に従い行った。Weeding effect Asakusa rate (asakusa rate relative to untreated area) 10
0 to less than 1% 9 1% or more to lO% // 8 10%/l to 20% // 7 20% to 30% // 6 30% to 40% 5 40% to 50% // 4 50%// ~ 60%/13 60
%// ~ 70% // 2 70% ~ 80%
// l 80%/l ~ 90%/10 90
% ~ 100% Degree of chemical damage: No chemical damage ±: Slight damage 12 Minor damage: Medium damage + 1 + 2 major damage Filled with paddy soil mixed with rice, and filled with two plants (2 Nipponbare) of paddy rice (variety Nihonbare) that had been grown in a greenhouse and had reached the two-leaf stage.
This 1st plant) was transplanted, and seeds of Nohie, Azena, Konagi, and Firefly were sown. 10 days after paddy rice transplantation and sowing20
After growing in a glass greenhouse at ~25°C, each compound shown in Table 3 was prepared into an aquarium according to Formulation Example 2, diluted with an appropriate amount of water so that the active ingredient was 1 kg per 1 ha, It was added dropwise with a pipette. The herbicidal effect and the degree of chemical damage were investigated according to the standards of Test Example 1 25 days after the chemical treatment.
その結果を表3に示す。The results are shown in Table 3.
Claims (2)
6のアルカノイル基であり、 R^2及びR^3は、それぞれ独立して 炭素数1〜6のアルキル基、炭素数2〜4のアルケニル
基、炭素数3または4のアルキニル基、置換されてもよ
いアリール基または置換されてもよいピリジニル基であ
る。 R^4、R^5、R^6及びR^7は、それぞれ独立し
て水素原子、ハロゲン原子、炭素数1〜6のアルキル基
、炭素数1〜6のハロアルキル基または炭素数1〜6の
アルコキシ基である] で表わされる2−ヒドラジノベンゾチアゾール誘導体。(1) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [However, R^1 is a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, or an alkyl group with 2 to 6 carbon atoms.
R^2 and R^3 are each independently an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 3 or 4 carbon atoms, or a substituted is an optionally substituted aryl group or an optionally substituted pyridinyl group. R^4, R^5, R^6 and R^7 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms. is an alkoxy group] A 2-hydrazinobenzothiazole derivative represented by the following.
6のアルカノイル基であり、 R^2及びR^3は、それぞれ独立して 炭素数1〜6のアルキル基、炭素数2〜4のアルケニル
基、炭素数3または4のアルキニル基、置換されてもよ
いアリール基または置換されてもよいピリジニル基であ
る。 R^4、R^5、R^6及びR^7は、それぞれ独立し
て水素原子、ハロゲン原子、炭素数1〜6のアルキル基
、炭素数1〜6のハロアルキル基または炭素数1〜6の
アルコキシ基である] で表わされる2−ヒドラジノベンゾチアゾール誘導体を
有効成分として含有する除草剤。(2) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [However, R^1 is a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, or an alkyl group with 2 to 6 carbon atoms.
R^2 and R^3 are each independently an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 3 or 4 carbon atoms, or a substituted is an optionally substituted aryl group or an optionally substituted pyridinyl group. R^4, R^5, R^6 and R^7 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms. An herbicide containing a 2-hydrazinobenzothiazole derivative represented by the following as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10536790A JPH045282A (en) | 1990-04-23 | 1990-04-23 | New 2-hydrazinobenzothiazole derivative and herbicide comprising the same derivative as active ingredient |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10536790A JPH045282A (en) | 1990-04-23 | 1990-04-23 | New 2-hydrazinobenzothiazole derivative and herbicide comprising the same derivative as active ingredient |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH045282A true JPH045282A (en) | 1992-01-09 |
Family
ID=14405747
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP10536790A Pending JPH045282A (en) | 1990-04-23 | 1990-04-23 | New 2-hydrazinobenzothiazole derivative and herbicide comprising the same derivative as active ingredient |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH045282A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001012604A1 (en) * | 1999-08-18 | 2001-02-22 | Aventis Cropscience Gmbh | Fungicides |
JPWO2008096675A1 (en) * | 2007-02-06 | 2010-05-20 | 日本曹達株式会社 | Lawn broadleaf perennial weed control agent and lawn broadleaf perennial weed control method |
-
1990
- 1990-04-23 JP JP10536790A patent/JPH045282A/en active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001012604A1 (en) * | 1999-08-18 | 2001-02-22 | Aventis Cropscience Gmbh | Fungicides |
US6939882B1 (en) | 1999-08-18 | 2005-09-06 | Aventis Cropsciences Gmbh | Fungicides |
JPWO2008096675A1 (en) * | 2007-02-06 | 2010-05-20 | 日本曹達株式会社 | Lawn broadleaf perennial weed control agent and lawn broadleaf perennial weed control method |
US8415273B2 (en) | 2007-02-06 | 2013-04-09 | Nippon Soda Co., Ltd. | Broadleaf perennial weed control agent for grass, and method for controlling broadleaf perennial weeds in grass |
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