WO2007057112A2 - Procede permettant de reduire la phytotoxicite des herbicides appliques sur des plants de riz - Google Patents

Procede permettant de reduire la phytotoxicite des herbicides appliques sur des plants de riz Download PDF

Info

Publication number
WO2007057112A2
WO2007057112A2 PCT/EP2006/010673 EP2006010673W WO2007057112A2 WO 2007057112 A2 WO2007057112 A2 WO 2007057112A2 EP 2006010673 W EP2006010673 W EP 2006010673W WO 2007057112 A2 WO2007057112 A2 WO 2007057112A2
Authority
WO
WIPO (PCT)
Prior art keywords
isothiazole
dichloro
carboxyl
methyl
herbicides
Prior art date
Application number
PCT/EP2006/010673
Other languages
English (en)
Other versions
WO2007057112A3 (fr
Inventor
Keiji Endo
Shinichi Shirakura
Teruyuki Ichihara
Original Assignee
Bayer Cropscience Ag
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 Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Publication of WO2007057112A2 publication Critical patent/WO2007057112A2/fr
Publication of WO2007057112A3 publication Critical patent/WO2007057112A3/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, 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
    • A01N43/80—Biocides, 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions

Definitions

  • the present invention relates to a method for reducing the phytotoxicity of herbicides applied to rice plants. More specifically, the present invention relates to a method for reducing the phytotoxicity of herbicides on paddy rice after transplantation of rice plant seedlings to a paddy field.
  • the present inventors have studied on reducing the phytotoxicity of herbicides applied to rice plants and, as a result, have now found that upon applying N- substituted 3,4-dichloro-isothiazole-5-carboxamide derivatives, as set forth in WO-A- 2004/103072 or WO-A-1999/24413, to rice plant seedlings during growing the seedlings, before transplanting them to a paddy field, the phytotoxicity on paddy rice after the transplantation can be markedly reduced.
  • the present invention provides a method for markedly reducing the phytotoxicity of herbicides on paddy rice after transplantation of rice plant seedlings to a paddy field, which method comprises, before the transplantation, applying an effective amount one or more N-substituted of 3,4-dichloro-isothiazole-5- carboxamide derivatives as safening compound to the rice plant seedlings.
  • R represents a group of the formula
  • R 1 represents cyano, phenyl or cycloalkyl having 3-7 carbon atoms, or
  • R represents a group of the formula in which
  • R 2 represents -C(CH 3 ) 3 , -CH(C 2 Hs) 2 , -CH(CH 3 )C 2 H 5 , cycloalkyl having 3-7 carbon atoms or -CH 2 -S-R 3 (in which R 3 represents alkyl having 1 -6 carbon atoms or phenyl which may be optionally substituted with halogen and/or alkyl having 1 -6 carbon atoms), or
  • R represents a group of the formula
  • R 4 represents hydrogen or N,N-dialkylaminomethyl having 1-4 carbon atoms in each alkyl part, or R represents a group of the formula
  • R 5 represents hydrogen or alkoxy having 1-4 carbon atoms
  • R 6 represents alkoxy having 1-4 carbon atoms, alkyl having 1 -6 carbon atoms, phenyl which may be optionally substituted with halogen or phenoxy which may be optionally substituted with halogen, or
  • R 5 represents phenoxy which may be optionally substituted with halogen
  • R 6 represents hydrogen, or
  • R represents a group of the formula
  • R 7 represents alkyl having 1-4 carbon atoms
  • R 8 represents alkyl having 1-4 carbon atoms
  • R 9 represents hydrogen or group of the formula
  • R represents a group of the formula
  • R 10 represents halogen, alkyl having 1-4 carbon atoms or alkoxy having 1 -4 carbon atoms, and n is an integer of 0-3, as effective component.
  • herbicidally active compounds suitable for the object of a reduction in phytotoxicity according to the method of the present invention may include, though not particularly limited to, the following compounds:
  • Acetamide type herbicides Pretilachlor, Butachlor, Alachlor,
  • Amide type herbicides Clomeprop, Bromobutide Benzofuran type herbicides: Benfuresate lndanedione type herbicides: lndanofan
  • Oxadinone type herbicides Oxadiclomefon
  • Sulfonylurea type herbicides Bensulfuron-methyl, Azimsulfuron, Imazosulfuron, Pyrazosulfuron-ethyl, Cyclosulfamuron,
  • Triazolopyrimidine type herbicides Penoxsulam
  • Thiocarbamate type herbicides Thiobencarb, Pyributicarb, Molinate Triazine type herbicides: Dimethametryn, Simetryn
  • Triazole type herbicides cafenstrole
  • Dithiophosphate type herbicides Anilofos
  • Oxyacetamide type herbicides Mefenacet Tetrazolinone type herbicides: Fentrazamide
  • Oxadiazolone type herbicides Oxadiargyl, Oxadiazon
  • Trione type herbicides Benzobicyclon, Mesotrione,
  • Phenoxypropionic acid type herbicides Cyhalofop-butyl, Metamifop, Fenoxaprop- ethyl, Fenoxaprop-P-ethyl, Pyriminoxy-benzoic acid type herbicides and analogues thereof: Bispyribac-sodium,
  • Diphenyl ether type herbicides Chlomethoxynil, Oxyfluorfen
  • Pyridine carbothioate type herbicides Dithiopyr Phenoxy type herbicides: MCPA, MCPB, 2,4-D
  • the compounds defined by their chemical name are also defined by the type of herbicide to which they belong and can be prepared in analogous manner like known herbicides from this type.
  • herbicide common names do not always express all specific salt or ester variants. These salts and esters are encompassed by the definition and, preferably encompass salts or esters as are commercially available and used.
  • the method of the present invention can exhibit a marked selective herbicidal effect between paddy rice and weeds.
  • weeds As a herbicidal spectrum, the following weeds can be exemplified.
  • Rotala indica (Rotala indica Koehne), False pimpernel (Lindernia procumbens Philcox), False loosestrife (Ludwigia prostrata Roxburgh), Largeleaf pondweed (Potamogeton distinctus A.
  • S. ⁇ -Dichloro-isothiazole- ⁇ -carboxyl ⁇ -cyanoanilide applied according to the present invention can be singly used but optionally in the form of diluted compound, or can be used in the form of a conventional formulation.
  • the forms of formulations may include, for example, a liquid agent, an emulsion, a hydrated agent, a flowable agent, a granule hydrating agent, a granulating agent, etc.
  • formulations can be prepared by the methods known per se. For example, they can be prepared by mixing the active compound with an extender, namely, a liquid diluent and/or a solid diluent, if necessary, using a surfactant such as an emulsifier and/or a dispersant.
  • an extender namely, a liquid diluent and/or a solid diluent
  • a surfactant such as an emulsifier and/or a dispersant.
  • Liquid diluents may include organic solvents such as, for example, aromatic hydrocarbons (for example, xylene, toluene, alkyl naphthalene or the like), chlorinated aromatic or chlorinated aliphatic hydrocarbons (for example, chlorobenzenes, ethylene chlorides, methylene chlorides or the like), aliphatic hydrocarbons [for example, cyclohexane or the like, or paraffins (for example, mineral oil fractions, mineral and vegetable oils, etc.)], alcohols (for example, butanol, glycol, and ethers and esters thereof, etc.), ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone or the like), and strong polar solvents (for example, dimethylformamide, dimethylsulfoxide, etc
  • organic solvents such as, for example, aromatic hydrocarbons (for example, xylene, tol
  • Solid diluents may include, for example, ammonium salts and pulverized natural minerals (for example, kaolin, clay, talc, chalk, quartz, attapulgite, montmorilonite, diatomite, etc.), pulverized synthetic minerals (for example, highly dispersing silicic acid, alumina, silicic salts, etc.). and the like.
  • pulverized natural minerals for example, kaolin, clay, talc, chalk, quartz, attapulgite, montmorilonite, diatomite, etc.
  • pulverized synthetic minerals for example, highly dispersing silicic acid, alumina, silicic salts, etc.
  • Usable solid carriers for granular agents include, for example, pulverized and fractionated rocks (for example, calcite, marble, pumice stone, meerschaum, dolomite, etc.), synthetic grains of organic or inorganic powders, fine particles of organic substances (for example, sawdust, coconut-shells, corn ear-stems, tobacco stalks, etc.), and the like.
  • pulverized and fractionated rocks for example, calcite, marble, pumice stone, meerschaum, dolomite, etc.
  • synthetic grains of organic or inorganic powders for example, sawdust, coconut-shells, corn ear-stems, tobacco stalks, etc.
  • Emulsifiers may include nonion and anion emulsifiers [for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers (such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, etc.), albumin hydrolysates, and the like.
  • nonion and anion emulsifiers for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers (such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, etc.), albumin hydrolysates, and the like.
  • Suitable dispersants include, for example, lignin-sulfite waste liquids and methyl cellulose.
  • Fixing or retaining agents may also be used in granular agents and the like, and such fixing or retaining agents may include, for example, carboxy methyl cellulose, natural and synthetic polymers (for example, gum arabic, polyvinyl alcohol, polyvinyl acetate, etc.), natural phosphatides (for example, cephalins, lecithins, etc.), synthetic phosphatides, and the like. Further, mineral and vegetable oils may also be used as additives.
  • Colorants may also be used, and such colorants may include inorganic pigments (for example, iron oxide, titanium oxide, Prussian blue, etc.); organic dyes such as alizarin dyes, azo dyes or metallic phthalocyanine pigments; and further a trace amount of such elements as, for example salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments for example, iron oxide, titanium oxide, Prussian blue, etc.
  • organic dyes such as alizarin dyes, azo dyes or metallic phthalocyanine pigments
  • such elements for example salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the effective amount of the effective component (safening compound), used according to the present invention is preferably within the range of from about 100 to about 600 g/ha, more preferably from about 200 to about 400 g/ha.
  • the above range may be optionally varied depending on the extent of occurrence of phytotoxicity and the strength thereof.
  • the separate application of the safening compound to the seedlings can be accomplished in various ways. For instance, a diluted formulation can be applied to the soil where the seedlings grow. Alternatively, the seedling box with the seedlings can be submerged in a diluted formulation of the safening compound. Another possible variant is spraying the diluted aqueous formulation of the safening compound onto the seedlings in the seedling box or onto the soil and the seedlings in the seedling box.
  • the seedlings are grown in plugs in a seedling box and the diluted formulation of the safening compound is applied to the plugs in the seedling box, either by submerging the plugs in the diluted formulation or by spraying the diluted formulation onto the plugs in the seedling box.
  • the latter method is preferred due to easy handling and good results.
  • H-4 Pretilachlor H-5: AVH301 (as aforementioned)
  • Carrier 5 parts by weight of acetone
  • Rice plant seedlings (Variety: Nihonbare) were grown in a seedling plug provided in a greenhouse until reaching the 2-leaf stage. Half the rice plant seedlings were transplanted into a pot (diameter: 16 cm, surface area: 200 cm 2 ) filled with alluvial epoch light soil which was submerged in water. Immediately thereafter, for each of the herbicidally active compounds, such as a test was carried out that a predetermined amount of the herbicidally active compound together with a predetermined amount (1000 g/ha) of the test compound S-1 were simultaneously applied onto the surface of the water.
  • a predetermined amount of the herbicidally active compound together with a predetermined amount (1000 g/ha) of the test compound S-1 were simultaneously applied onto the surface of the water.
  • the remaining half the rice plant seedlings were treated with a predetermined amount (200 g/ha or 400 g/ha) of the test compound S-1 in a submerged application manner one day before the transplantation, followed by transplanting them to the pot, and immediately thereafter, applying a predetermined amount of each of the herbicidally active compound under test onto the surface of the water.
  • a predetermined amount 200 g/ha or 400 g/ha
  • the test compound S-1 was treated with a predetermined amount (200 g/ha or 400 g/ha) of the test compound S-1 in a submerged application manner one day before the transplantation, followed by transplanting them to the pot, and immediately thereafter, applying a predetermined amount of each of the herbicidally active compound under test onto the surface of the water.
  • Twenty one days after the treatment with each of the herbicidally active compound under test phytotoxicity on the rice plants was observed and evaluated. The criterion of the evaluation was as follows: 0 % indicates no phytotoxicity, and 100 % indicates the complete death. The

Landscapes

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

Abstract

La présente invention concerne un procédé permettant de réduire la phytotoxicité des herbicides sur du riz paddy après avoir transplanté de jeunes plants de riz dans une rizière. Ledit procédé consiste à appliquer, avant ladite transplantation, un ou plusieurs dérivés N substitués de 3,4-dichloro-isothiazole-5-carboxamide sur les jeunes plants de riz.
PCT/EP2006/010673 2005-11-21 2006-11-08 Procede permettant de reduire la phytotoxicite des herbicides appliques sur des plants de riz WO2007057112A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2005335263A JP4926459B2 (ja) 2005-11-21 2005-11-21 薬害軽減方法
JP2005-335263 2005-11-21

Publications (2)

Publication Number Publication Date
WO2007057112A2 true WO2007057112A2 (fr) 2007-05-24
WO2007057112A3 WO2007057112A3 (fr) 2007-07-26

Family

ID=37950216

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/010673 WO2007057112A2 (fr) 2005-11-21 2006-11-08 Procede permettant de reduire la phytotoxicite des herbicides appliques sur des plants de riz

Country Status (3)

Country Link
JP (1) JP4926459B2 (fr)
TW (1) TW200735777A (fr)
WO (1) WO2007057112A2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009124708A2 (fr) * 2008-04-09 2009-10-15 Bayer Cropscience Ag Procédé de réduction de la phytotoxicité
EP2468097A1 (fr) * 2010-12-21 2012-06-27 Bayer CropScience AG Utilisation d'isothiazolecarboxamides pour créer des défenses latentes de l'hôte dans une plante
WO2013064619A1 (fr) 2011-11-04 2013-05-10 Bayer Intellectual Property Gmbh Procédé de prévention des maladies du riz greffé
CN103918667A (zh) * 2014-04-24 2014-07-16 深圳诺普信农化股份有限公司 杀菌组合物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999024413A2 (fr) * 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Amides d'acide isothiazol carboxylique et leur utilisation pour la protection de plantes
WO2004103072A1 (fr) * 2003-05-23 2004-12-02 Bayer Cropscience Aktiengesellschaft Nouveaux phytoprotecteurs et leur utilisation
WO2005009130A1 (fr) * 2003-07-23 2005-02-03 Bayer Cropscience Aktiengesellschaft Associations de principes actifs fongicides
WO2005009131A1 (fr) * 2003-07-23 2005-02-03 Bayer Cropscience Aktiengesellschaft Associations de substances actives fongicides

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5791901A (en) * 1980-11-28 1982-06-08 Nippon Kayaku Co Ltd Method of reducing chmical injury to rice plant
JPS6176403A (ja) * 1984-09-20 1986-04-18 Zenkoku Nogyo Kyodo Kumiai Rengokai 作物の薬害軽減剤
JPH1160409A (ja) * 1997-08-20 1999-03-02 Nissan Chem Ind Ltd 除草剤の薬害を軽減する組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999024413A2 (fr) * 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Amides d'acide isothiazol carboxylique et leur utilisation pour la protection de plantes
WO2004103072A1 (fr) * 2003-05-23 2004-12-02 Bayer Cropscience Aktiengesellschaft Nouveaux phytoprotecteurs et leur utilisation
WO2005009130A1 (fr) * 2003-07-23 2005-02-03 Bayer Cropscience Aktiengesellschaft Associations de principes actifs fongicides
WO2005009131A1 (fr) * 2003-07-23 2005-02-03 Bayer Cropscience Aktiengesellschaft Associations de substances actives fongicides

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
MIYAUCHI NOBUYOSHI ET AL: "Differential safening activity of dymron and fenclorim on pretilachlor injury in rice seedlings in soil" WEED BIOLOGY AND MANAGEMENT, vol. 2, no. 1, 2002, pages 46-51, XP002432817 ISSN: 1444-6162 *
USUI KENJI: "Metabolism and selectivity of rice herbicides in plants" WEED BIOLOGY AND MANAGEMENT, vol. 1, no. 3, 2001, pages 137-146, XP002432818 ISSN: 1444-6162 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009124708A2 (fr) * 2008-04-09 2009-10-15 Bayer Cropscience Ag Procédé de réduction de la phytotoxicité
WO2009124708A3 (fr) * 2008-04-09 2010-04-22 Bayer Cropscience Ag Procédé de réduction de la phytotoxicité
EP2468097A1 (fr) * 2010-12-21 2012-06-27 Bayer CropScience AG Utilisation d'isothiazolecarboxamides pour créer des défenses latentes de l'hôte dans une plante
WO2012084858A2 (fr) * 2010-12-21 2012-06-28 Bayer Cropscience Ag Utilisation de carboxamides d'isothiazole pour créer des défenses hôtes latentes chez une plante
WO2012084858A3 (fr) * 2010-12-21 2012-08-16 Bayer Cropscience Ag Utilisation de carboxamides d'isothiazole pour créer des défenses hôtes latentes chez une plante
CN103260411A (zh) * 2010-12-21 2013-08-21 拜耳知识产权有限责任公司 异噻唑甲酰胺建立植物中的潜在宿主防御的用途
WO2013064619A1 (fr) 2011-11-04 2013-05-10 Bayer Intellectual Property Gmbh Procédé de prévention des maladies du riz greffé
CN103918667A (zh) * 2014-04-24 2014-07-16 深圳诺普信农化股份有限公司 杀菌组合物

Also Published As

Publication number Publication date
JP2007137833A (ja) 2007-06-07
JP4926459B2 (ja) 2012-05-09
TW200735777A (en) 2007-10-01
WO2007057112A3 (fr) 2007-07-26

Similar Documents

Publication Publication Date Title
EP1976384B1 (fr) Composition herbicide pour rizière
JP5984896B2 (ja) 混合除草剤組成物
AU2005230239B2 (en) Difluoromethanesulfonyl anilide derivatives useful as herbicides
CN1378424A (zh) 基于n－芳基－三唑啉(硫)酮的选择性除草剂
JP2011530552A (ja) ジメトキシトリアジニル置換ジフルオロメタンスルホニルアニリド類を含む除草剤／薬害軽減剤の組み合わせ
WO2007057112A2 (fr) Procede permettant de reduire la phytotoxicite des herbicides appliques sur des plants de riz
EP0558999A2 (fr) Dérivés de pyrazole N-arylé comme herbicides
DE4414568A1 (de) Heterocyclylbenzonitrile
EP0584655A2 (fr) 3-Aryl-triazine-2,4-diones comme herbicides
KR100563144B1 (ko) 선택적 제초제 조성물
EP0537539A1 (fr) 2-(2-Benzoxazolyl-oxy)-acetamides et leur utilisation comme herbicides
JPH0551304A (ja) 除草剤組成物
WO2004105482A2 (fr) Compositions herbicides pour riziere
EP0573882A1 (fr) 2-(7-Chloro-2-benzoxazolyloxy)-acétamide et leur utilisation comme herbicides
EP0537543A1 (fr) 2-(2-(fluorophényl)-1,3,4-thiadiazol-5-yl-oxy)-acétamides utiles comme herbicides
JPH09241109A (ja) 除草剤組成物
EP0528212A1 (fr) N-azinyl-N'-(2-éthylsulfinyl-phénylsulfonyl)urées comme herbicides
DE19530451A1 (de) Substituierte Chinazolin(thi)one
DE4438001A1 (de) Herbizide Mittel auf Basis von N-(4-Fluor-phenyl)-N-isopropylchloracetamid und Verfahren zur Herstellung dieser Verbindung

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase in:

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 06806702

Country of ref document: EP

Kind code of ref document: A2