+

WO1998028981A1 - Composition herbicide - Google Patents

Composition herbicide Download PDF

Info

Publication number
WO1998028981A1
WO1998028981A1 PCT/JP1997/004816 JP9704816W WO9828981A1 WO 1998028981 A1 WO1998028981 A1 WO 1998028981A1 JP 9704816 W JP9704816 W JP 9704816W WO 9828981 A1 WO9828981 A1 WO 9828981A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
herbicidal
herbicidal composition
hydrogen atom
alkyl group
Prior art date
Application number
PCT/JP1997/004816
Other languages
English (en)
Japanese (ja)
Inventor
Masami Koguchi
Akihiro Takahashi
Shigeo Yamada
Takashi Kawana
Original Assignee
Nippon Soda Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nippon Soda Co., Ltd. filed Critical Nippon Soda Co., Ltd.
Publication of WO1998028981A1 publication Critical patent/WO1998028981A1/fr

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present invention relates to a herbicidal composition which, by mixing two herbicides, exhibits a synergistic effect as well as an additive effect of the individual herbicides.
  • Pyrazole compounds which are one active ingredient of the herbicidal composition of the present invention, are disclosed in WO96 / 26206, WO97 / 411105 and WO97 ⁇ 4111 It is described in the official gazette.
  • R ', R 2 each independently represent a hydrogen atom, C, and e alkyl group
  • M, L are each independently a hydrogen atom, a halogen atom, C, - 6 alkyl group , C, - «alkoxy group, S 0 2 R 3 (R 3 is;. represents an alkyl group), etc. represent
  • Z is also saturated 5 or 6 membered properly a heterocyclic group unsaturated represents
  • R 4 represents a a group represented by the hydrogen atom or S 0 2 a r.
  • An object of the present invention is to provide a herbicidal composition which is safe for corn and wheat and can be completely controlled from a one-year to a perennial weed at a low dose.
  • DISCLOSURE OF THE INVENTION The present inventors have added to the compounds represented by the formula [I] below, atrazine, isoprolone, cyanadine, chlorotoluron, benzozone, and xyoxinil. It has been found that when one or two or more photosynthesis inhibitors such as the above are mixed in a predetermined ratio, not only the respective herbicidal effects can be obtained additively but also a synergistic herbicidal effect appears. .
  • the combined use of the two drugs expands the range of weed killing beyond the application range obtained with each single agent, and at the same time achieves faster completion of the weed killing effect.
  • the present inventors have found that a sufficient effect can be exerted at a dose lower than the dose, as well as the safety against corn and wheat, and that a single treatment can exhibit a sufficient herbicidal effect, thereby completing the present invention.
  • the present invention provides a compound of the formula [I]
  • R 1 and R 2 each independently represent a hydrogen atom, an alkyl group or a C alkenyl group
  • M and L each independently represent a hydrogen atom, a halogen atom, C, — «; alkyl Group, alkoxy group, SR 3 , S 0 R 3 , S 0 R 3
  • R 3 represents a C, — "alkyl group.), A cyano group or a nitro group, Z represents a 5- or 6-membered saturated or unsaturated heterocyclic group, and R 4 represents A hydrogen atom, a group represented by CH 2 A r, CH 2 C 0 A r or S 0 2 A r (A r has a substituent P97 / 04816 represents a funinyl group which may be substituted. ).
  • a herbicidal composition comprising a biazole compound represented by the formula: and a photosynthesis inhibitor.
  • BEST MODE FOR CARRYING OUT THE INVENTION The composition of the present invention generally depends on the relative activity of each component, but is generally a compound represented by the above formula [I] per 1 part by weight of a photosynthesis inhibitor. Is contained in an amount of 0.0001 to 50 parts by weight, preferably 0.001 to 10 parts by weight.
  • One active ingredient of the composition of the present invention is a compound represented by the formula [I].
  • R 1 and R 2 are each independently a hydrogen atom, methyl, ethyl, propyl, isopropyl, butyl, isoptyl, sec-butyl, butyl, etc. — Represents a G alkyl group, or C,-(i alkenyl group such as 1-probenyl, 2-provenyl, 1-butenyl, 2-butenyl, 3-butenyl group.
  • M and L are each independently a hydrogen atom, a halogen atom such as fluorine, chlorine, bromine, or iodine, methyl, ethyl, propyl, isopropyl, butyl, isoptyl, sec-butyl, t-butyl group C alkyl group, such as, main butoxy, et butoxy, Purobokishi, C, such as Lee isopropoxy group, -; alkoxy group, main Chiruchio, Echiru Chio, a group represented by SR 3, such as a propylthio group, Mechirusurufu Weniru, Echiru Surufuweniru , A group represented by S 0 R : i such as a propylsulfenyl group; a group represented by S 0 2 R 3 such as a methylsulfonyl, ethylsulfonyl, and propylsulfonyl group (R
  • Z represents a 5- or 6-membered saturated or unsaturated heterocyclic group.
  • Examples of the 5-membered unsaturated heterocyclic group represented by Z include 2-furyl, 3-furyl, 2-phenyl, 3-phenyl, 2-pyrrolyl, 3-pyrrolyl, 2 — oxazolyl, 4 year old oxazolyl, 5 — year old oxazolyl, 3 — isosoxazolyl, 4 ⁇ 1 oxoxazolyl, 5 — isosoxazolyl, 3 — isisothiazolyl, 4 ⁇ 1 isothiazolyl, 5 — a Sothiazolyl, 2 — imidazolyl, 4 — imidazolyl, 3 — villazolyl, 4 1 villazolyl, 1, 2, 4 oxaziazoloneru 3 — yl, 1, 2, 4 — oxaziazolulu 5 —Ill, 1,3,4 Oxazia
  • 6-membered unsaturated heterocyclic groups include 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyridinyl, 3-pyrazinyl, 2-pyrimidinyl, and 4-pyridinyl. Midinyl, 5—pyrimidinyl, 3—pyridazinyl, 4-pyridazinyl, 1,3,5—triazine-1-2-yl, 1,2,4, triazine-1-5-yl , 1, 2, 4 — Triazine 1-3-yl, 1, 2, 4-Triazine 6-yl, 1, 2, 4, 5 — Tetrazine 1-3-yl group And the like.
  • saturated 5- or 6-membered heterocyclic groups include 2-tetrahydrofuranil, 3-tetrahydrofuranyl, 2-tetrahydrochenyl, and 3-tetrahydrofuranyl.
  • Trahidrochirenil Tetrahidrochiopyran-1 2-yl, Tetrahidrochiopyran-1 3-yl, Tetrahidrochiopyran_41-yl, 1,3—Dithia N 1 2 — yl, 1,
  • R represents a hydrogen atom, CH 2 A r, the group represented by CHC 0 A r or S 0 2 A r.
  • Ar is located at any position on the benzene ring, such as halogen atoms such as fluorine, chlorine and bromine, and-, such as methyl groups, alkyl groups, and methoxy groups, etc.
  • the compound represented by the formula [I] has excellent herbicidal activity by itself. In particular, it has little phytotoxicity to corn and wheat, and has an excellent herbicidal effect against weeds such as ginkgo biloba, crabgrass, embak, ichibi, and inubu.
  • Ts represents a 4-toluenesulfonyl group; the same applies hereinafter Table 2 (continued)
  • the photosynthesis inhibitor which is another active ingredient of the composition of the present invention, has relatively low phytotoxicity to grasses such as corn and barley, and is a broadleaf weed such as nubu, ichibi and blackgrass. It is a herbicide that is active on a very small number of grass weeds and is characterized by many drugs with a narrow herbicidal spectrum.
  • Such photosynthesis inhibitors include, for example, atrazine, isoprolone, cyanadine, chlorotoluron, benzazone, and ioxynil.
  • the herbicidal composition of the present invention can be used in the form of a mixture without adding other components, or in a form that can be taken by a general pesticide for use as a pesticide. That is, they can be used in the form of wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, flowables and the like.
  • plant powders such as soybean flour and flour, diatomaceous earth, apatite, gypsum, talc, bentona Mineral powders such as it, pyrophyllite and clay, and organic and inorganic compounds such as sodium benzoate, urea and sodium sulfate are used.
  • organic and inorganic compounds such as sodium benzoate, urea and sodium sulfate are used.
  • petroleum components such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetate , Trichloroethylene, methylisobutylketone, mineral oil, vegetable oil, water, etc. are used as solvents.
  • a surfactant can be added, if necessary, to obtain a uniform and stable form.
  • the wettable powder and emulsion thus obtained are diluted to a predetermined concentration with water to form a suspension or an emulsion, and the granules are used as they are before or after germination of the weeds. Spraying or soil mixing. Actually, in applying the herbicide of the present invention, an appropriate amount of 0.1 g or more of the active ingredient per hectare is applied.
  • the individual active compounds often exhibit disadvantages in their herbicidal activity, however, if they are greater than the simple sum (the expected value) of the respective activities of the two compounds. This is called a synergistic effect.
  • the expected activity of a particular combination of two herbicides can be calculated as follows (Co 1 by S, R. Calculation of synergistic and antagonistic response of a herbicide combination "W eeds ", Vol. 15, pages 20-22, 1967.
  • indices of 3, 5, 7, and 9 indicate values intermediate between 0, 22, 22, 44, 6, 6, 88, and 10, respectively.
  • the herbicidal composition of the present invention is suitable as a herbicide for controlling corn and wheat weeds and is industrially useful.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Cette invention concerne une composition herbicide comportant un composé pyrazole représenté par la formule générale (I) et un inhibiteur de photosynthèse du type atrazine ou isoproturon. Dans la formule (I), R1 et R2 sont indépendamment hydrogène, alkyle C¿1-6?, etc.; M et L sont indépendamment hydrogène, halogéno, alkyle C1-6, alcoxy C1-6, SO2R?3 (où R3¿ est alkyle C¿1-6?), etc.; Z représente un hétérocycle (in)saturé à cinq ou six éléments; et R?4¿ est hydrogène, un groupe représenté par CH¿2?Ar ou SO2Ar (où Ar représente un phényle éventuellement substitué), etc.
PCT/JP1997/004816 1996-12-27 1997-12-25 Composition herbicide WO1998028981A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP8/360067 1996-12-27
JP36006796 1996-12-27

Publications (1)

Publication Number Publication Date
WO1998028981A1 true WO1998028981A1 (fr) 1998-07-09

Family

ID=18467743

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1997/004816 WO1998028981A1 (fr) 1996-12-27 1997-12-25 Composition herbicide

Country Status (1)

Country Link
WO (1) WO1998028981A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0900795A1 (fr) * 1996-04-26 1999-03-10 Nippon Soda Co., Ltd. Derives du benzene substitues par des heterocycles, et herbicides
WO1999065314A1 (fr) * 1998-06-16 1999-12-23 Basf Aktiengesellschaft Melanges herbicides a effet synergique
WO2001028341A3 (fr) * 1999-10-22 2002-05-02 Aventis Cropscience Gmbh Agents herbicides synergetiques contenant des herbicides faisant partie du groupe des inhibiteurs de l'hydroxyphenylpyruvate dioxygenase
US6433082B1 (en) 1998-06-26 2002-08-13 Bayer Aktiengesellschaft Herbicidal mixtures exhibiting a synergistics effect
US6610631B1 (en) 1999-09-30 2003-08-26 Bayer Aktiengesellschaft Substituted aryl ketones
US6746989B1 (en) 1999-03-27 2004-06-08 Bayer Aktiengesellschaft Substituted benzoylpyrazoles as herbicides
US6864219B2 (en) 2000-01-17 2005-03-08 Bayer Aktiengesellschaft Substituted aryl ketones
US7112554B2 (en) 2001-05-09 2006-09-26 Bayer Cropscience Ag Substituted arylketones
US7153813B2 (en) 2002-02-19 2006-12-26 Bayer Aktiengesellschaft Substituted aryl ketones
US7807703B2 (en) 2002-03-05 2010-10-05 Bayer Cropscience Ag Substituted aryl ketones

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996026206A1 (fr) * 1995-02-24 1996-08-29 Basf Aktiengesellschaft Derives de pyrazol-4-yl-benzoyle et leur utilisation comme herbicides
WO1997041105A1 (fr) * 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Nouveaux derives de benzene a substitution heterocycle et herbicides
WO1997041117A1 (fr) * 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Nouveaux derives du benzene substitues par des heterocycles, et herbicides
WO1997041118A1 (fr) * 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Derives du benzene substitues par des heterocycles, et herbicides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996026206A1 (fr) * 1995-02-24 1996-08-29 Basf Aktiengesellschaft Derives de pyrazol-4-yl-benzoyle et leur utilisation comme herbicides
WO1997041105A1 (fr) * 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Nouveaux derives de benzene a substitution heterocycle et herbicides
WO1997041117A1 (fr) * 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Nouveaux derives du benzene substitues par des heterocycles, et herbicides
WO1997041118A1 (fr) * 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Derives du benzene substitues par des heterocycles, et herbicides

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0900795A4 (fr) * 1996-04-26 2000-12-13 Nippon Soda Co Derives du benzene substitues par des heterocycles, et herbicides
EP0900795A1 (fr) * 1996-04-26 1999-03-10 Nippon Soda Co., Ltd. Derives du benzene substitues par des heterocycles, et herbicides
US7842646B2 (en) 1998-06-16 2010-11-30 Basf Se Synergistically acting herbicidal mixtures
WO1999065314A1 (fr) * 1998-06-16 1999-12-23 Basf Aktiengesellschaft Melanges herbicides a effet synergique
JP4646403B2 (ja) * 1998-06-16 2011-03-09 ビーエーエスエフ ソシエタス・ヨーロピア 相乗効果を有する除草剤混合物
JP2002518303A (ja) * 1998-06-16 2002-06-25 ビーエーエスエフ アクチェンゲゼルシャフト 相乗効果を有する除草剤混合物
US6534444B1 (en) 1998-06-16 2003-03-18 Basf Aktiengesellschaft Herbicidal mixtures having a synergistic effect
US6908883B2 (en) 1998-06-16 2005-06-21 Basf Ag Synergistically acting herbicidal mixtures
US6433082B1 (en) 1998-06-26 2002-08-13 Bayer Aktiengesellschaft Herbicidal mixtures exhibiting a synergistics effect
US6746989B1 (en) 1999-03-27 2004-06-08 Bayer Aktiengesellschaft Substituted benzoylpyrazoles as herbicides
US7279444B2 (en) 1999-03-27 2007-10-09 Bayer Cropscience Gmbh Substituted benzoylpyrazoles
US6727206B2 (en) 1999-09-30 2004-04-27 Bayer Aktiengesellschaft Substituted aryl ketones
US6610631B1 (en) 1999-09-30 2003-08-26 Bayer Aktiengesellschaft Substituted aryl ketones
EP1913816A3 (fr) * 1999-10-22 2012-05-23 Bayer CropScience AG Agents herbicides synergétiques contenant des herbicides faisant partie du groupe des inhibiteurs de l'hydroxyphenylpyruvate dioxygenase
WO2001028341A3 (fr) * 1999-10-22 2002-05-02 Aventis Cropscience Gmbh Agents herbicides synergetiques contenant des herbicides faisant partie du groupe des inhibiteurs de l'hydroxyphenylpyruvate dioxygenase
US6864219B2 (en) 2000-01-17 2005-03-08 Bayer Aktiengesellschaft Substituted aryl ketones
US7456133B2 (en) 2001-05-09 2008-11-25 Bayer Cropscience Ag Substituted arylketones
US7112554B2 (en) 2001-05-09 2006-09-26 Bayer Cropscience Ag Substituted arylketones
US7153813B2 (en) 2002-02-19 2006-12-26 Bayer Aktiengesellschaft Substituted aryl ketones
US7807703B2 (en) 2002-03-05 2010-10-05 Bayer Cropscience Ag Substituted aryl ketones

Similar Documents

Publication Publication Date Title
ES2238425T3 (es) Composicion herbicida.
JP3728324B2 (ja) 1−置換−4−カルバモイル−1,2,4−トリアゾール−5−オン誘導体及び除草剤
KR20100110815A (ko) 살균제 이환식 피라졸
BRPI0806894A2 (pt) Derivados de piridazina, processos para sua preparação e seu uso como fungicidas
SK5372002A3 (en) Synergistic herbicidal agents that contain herbicides from the group of the hydroxyphenylpyruvate dioxygenase inhibitors, a method for killing harmful plants and use of said agents for killing harmful plants
KR20190025695A (ko) 복소환 화합물 및 그것을 함유하는 유해 절족 동물 방제제
JPH0624914A (ja) 殺生物剤
WO1998028981A1 (fr) Composition herbicide
AU2002325217B2 (en) Herbicidal agents containing benzoylpyrazoles and safeners
WO2022033906A1 (fr) Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acide aminé f129l dans la protéine cytochrome b mitochondriale conférant une résistance à des inhibiteurs qo viii
KR20220019763A (ko) 신규한 비코딩 헤테로사이클릭 아미노산(nchaa) 및 그것의 제초제로서의 용도
JPS62267211A (ja) 除草剤組成物
CN108059629B (zh) 含嘧啶的取代吡唑类化合物及其制备方法和用途
AU2002225656B2 (en) Herbicidal heterocycles
KR100424908B1 (ko) 상승 작용을 갖는 제초제 조성물 및 잡초 방제법
WO2017134446A1 (fr) Association d'herbicides
TW202126659A (zh) 7-氧雜-3,4-二氮雜雙環[4.1.0]庚-4-烯-2-酮化合物及除草劑
JPH02184676A (ja) 新規の除草活性のあるn‐フェニル‐アゾール
JPS63126804A (ja) 農園芸用殺虫組成物
DE69230003T2 (de) Substituierte pyridincarbonsäurederivate als herbizide
UA119999C2 (uk) Заміщена похідна піразолілпіразолу та її застосування як гербіциду
WO1997035481A1 (fr) Composition herbicide
JPS5976005A (ja) 殺菌剤および殺菌法
WO1993003617A1 (fr) Composition insecticide
JP3563174B2 (ja) 水田用除草剤組成物

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA JP US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
点击 这是indexloc提供的php浏览器服务,不要输入任何密码和下载