EP1423010A2 - Selektive herbizide enthaltend ein tetrazolinon-derivat - Google Patents

Selektive herbizide enthaltend ein tetrazolinon-derivat

Info

Publication number
EP1423010A2
EP1423010A2 EP02792557A EP02792557A EP1423010A2 EP 1423010 A2 EP1423010 A2 EP 1423010A2 EP 02792557 A EP02792557 A EP 02792557A EP 02792557 A EP02792557 A EP 02792557A EP 1423010 A2 EP1423010 A2 EP 1423010A2
Authority
EP
European Patent Office
Prior art keywords
methyl
chloro
ethyl
phenyl
alkyl
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.)
Withdrawn
Application number
EP02792557A
Other languages
German (de)
English (en)
French (fr)
Inventor
Helmut FÜRSCH
Dieter Feucht
Thomas König
Hartwig Mooban Exclusive 39 DAUCK
Felicitos V. Palis
Ruperto P. Basilio
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
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 EP1423010A2 publication Critical patent/EP1423010A2/de
Withdrawn legal-status Critical Current

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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms

Definitions

  • the invention relates to new herbicidal, synergistic active ingredient combinations which, on the one hand, and a known, herbicidally active compound are derived from a known tetrazolinone derivative
  • tetrazolinone derivative 4- (2-chlorophenyl) -N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-lH-tetrazole-1-carboxamide (common name: fentrazamide) is alone or as a broadly active herbicide in admixture with other herbicides the subject of a number of patent applications (cf. US 5,362,704; JP 11335212 A; JP 2000239111 A; JP 10330202; JP 09241109 A; JP 09012406 A; US 5,928,991; WO 00/003591; WO 00/003597).
  • the known herbicidal combinations have a number of
  • the compound 4- (2-chloropheny ⁇ ) -N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide when used together with known herbicidally active compounds shows distinct synergistic effects with regard to the action against weeds in various substance classes and is particularly advantageous as a broadly effective combination preparation for the selective control of weeds in crops such as, for example Rice can be used.
  • the invention relates to selective herbicidal compositions, characterized by an effective content of an active ingredient combination comprising
  • R1 hydrogen, (C r C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 5 -C 6 ) cycloalkenyl, phenyl or 3- to 6-membered Heterocyclyl with up to three heteroatoms from the group nitrogen, oxygen and sulfur, the six latter radicals optionally being substituted by one or more, identical or different substituents from the group halogen, (C 1 -C 6 ) alkoxy, (C -C 6 ) -Haloalkoxy, (C 1 -C 2 ) alkylsulfmyl, (C r C 2 ) alkylsulfonyl 5 (C 3 -C 6 ) cycloalkyl, (C r C 4 ) alkoxycarbonyl, (C ⁇ -C 4 ) alkylcarbonyl and phenyl and in the case of cyclic radicals also (-CC
  • R 2 is hydrogen, (C r C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, the three last-mentioned radicals optionally being substituted by one or more, identical or different substituents from the Group halogen, hydroxy, (C r C 4 ) alkyl, (C r C 4 ) alkoxy and (C r C 4 ) alkylthio are substituted;
  • R 3 halogen, (C r C 4 ) haloalkyl 5 (C r C 4 ) haloalkoxy, nitro, (C ! -C 4 ) alkyl, (C r C 4 ) alkoxy, (C r C 4 ) - Alkylsulfonyl, (C 1 -C 4 ) alkoxycarbonyl or (C 1 -C 4 ) alkylcarbonyl;
  • R 4 is hydrogen or methyl; R5 halogen, nitro, (C r C 4 ) alkyl, (C r C 4 ) haloalkyl, (C r C 4 ) haloalkoxy, (C 3 -C 6 ) cycloalkyl, phenyl, (C r C 4 ) -alkoxy, cyano, (C r C 4 ) -alkylthio, (C r C 4 ) -alkylsulfmyl, (C 1 -C 4 ) -alkylsulfonyl, (C r C 4 ) -alkoxycarbonyl or (C 1 -C4) alkylcarbonyl;
  • Rl is hydrogen, (C r C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, furanyl or thienyl, each of the latter four radicals unsubstituted or by one or more substituents from the group halogen, (Cj-C 4 ) -Alkoxy, halogen- (C r C 6 ) -alkoxy and (C 1 -C 4 ) -alkylthio and in the case of cyclic radicals also (C 1 -C 4 ) -alkyl and (C 1 -C 4 ) -haloalkyl is substituted ;
  • R 2 is hydrogen or methyl; , R3 is halogen, halo (C r C 4) alkoxy alkyl 3 halo ⁇ -C 4) (C r C 4) - alkyl, (C r C4) alkoxy, (C r C4) -alkylsulfonyl ; (C r C 4 ) alkoxycarbonyl, (C 1 -C) alkylcarbonyl;
  • R 4 is hydrogen, methyl
  • R 5 halogen, (C r C 4 ) alkyl, halogen (C r C 4 ) alkyl, halogen (C r C 4 ) alkoxy, (C 3 -C 6 ) cycloalkyl, phenyl, (C r C 4 ) alkoxy, cyano, (C r C 4 ) alkylthio, (Ci-C ⁇ alkylsulfinyl, (C r C 4 ) alkylsulfonyl, (C r C 4 ) alkoxycarbonyl, (C 1 -C 4 ) alkylcarbonyl;
  • n 1 or 2
  • alkali metal salts in particular the sodium salts (known from DE-Al-19 621 522)
  • the active compound combinations defined above from the tetrazolinone derivative of the formula (I) and the above-mentioned active compounds from group 2 in combination with active compounds from group 3, with very good crop plant tolerance have a particularly high herbicidal activity and in various crops, especially in rice, but also in maize and cereals for selective weed control.
  • the active substance combinations defined above consist of the tetrazolinone derivative of the formula (I) and a safener / antidote
  • Active ingredients of group 3 in combination with one or more of the above-mentioned active ingredients of group 2 with very good crop tolerance, have a particularly high herbicidal activity and in different crops, in particular in cereals, especially wheat, but also in soybeans , Potatoes, corn and rice can be used for selective weed control.
  • compositions according to the invention can be modified to the extent that they contain one or more of the following active ingredients in addition to components (a) and (b) as the third or further herbicidal active ingredient:
  • Methyl dimethoxy-pyrimidin-2-yl-oxy) benzoate (pyriminobac-methyl), 2-chloro-6- (4,6-dimethoxy-pyrimidin-2-ylthio) -benzoic acid sodium salt (pyrithiobac-sodium), 3 , 7-dichloro-quinoline-8-carboxylic acid (Quinchlorac), 7-chloro-3-methyl-quinoline-8-carboxylic acid (Quinmerac), 2- [4- (6-chloro-2-quinoxalinyloxy) phenoxy] propanoic acid (-ethyl ester, -tetrahydro-2-furanyl-methyl ester) (quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- ( 3-ethylsulfonyl-pyridin
  • Benthiocarb (Thiobencarb) Benthiocarb + chlorine nitrofen
  • the active substance combinations according to the invention can e.g. can be used in the following plants:
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants according to the invention with the active compounds is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, for example by dipping, spraying, Evaporation, nebulization, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by means of single- or multi-layer coating.
  • the synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios. However, they can
  • Weight ratios of the active ingredients in the active ingredient combinations can be varied in relatively large ranges.
  • 1 to 1 part by weight of active compound of the formula (I) accounts for 0.01 to 1000 parts by weight, preferably 0.1 to 100 parts by weight and particularly preferably 0.1 to 10 parts by weight of active compound of group 2.
  • the advantageous effect of the crop plant tolerance of the active compound combinations according to the invention is also particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 1 part by weight of active compound of the formula (I) or mixtures thereof are present
  • Active ingredients of group 2 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight and particularly preferably 0.1 to 10 parts by weight of one of the compounds (antidots / safeners) which improve crop plant tolerance and are mentioned above under (c).
  • the active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders ie liquid solvents and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • Chloroethylene or methylene chloride Chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water
  • Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
  • non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active ingredients, including the safing active ingredients, preferably between 0.5 and
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the active ingredients contained in the active ingredient combinations can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
  • the new combinations of active ingredients can furthermore also be used in a mixture with other known herbicides, finished formulations or tank mixtures again being possible. Also one
  • the new combinations of active ingredients as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules are used. They are used in the customary manner, for example by watering, spraying, spraying, dusting or scattering.
  • the active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say in the pre-emergence and post-emergence process. They can also be worked into the soil before sowing.
  • Herbicides always have a synergistic effect if the herbicidal activity of the active ingredient combination is greater than that of the individual active ingredients applied.
  • a concentration corresponding to a water application rate of 200 l / ha is set.
  • Rice seeds are sown on trial plots (2 mx 5 m) in rice fields. 10 days after sowing (in the 1 - 2 leaf stage of the rice), the spray preparation is applied to the test areas (application with a sprayer). 1 month after the treatment, the soil is dammed up to a water depth of 5 cm; the flooding conditions are kept constant.
  • the active substance preparations are mixed with water.
  • a concentration corresponding to a water application rate of 200 l / ha is set.
  • Rice seeds are sown on trial plots (2 mx 5 m) in rice fields. 29 days after sowing (in the development stage BBCH 23 of the rice; start of tillering), the spray preparation is applied to the test areas (application with a sprayer). A few days after the treatment, the
  • Echinochloa crus-galli and Brachiaria plantaginea rated in comparison to an untreated control.
  • the active substance preparations are mixed with water.
  • a concentration corresponding to a water application rate of 200 l / ha is set.
  • Rice seeds are sown on trial plots (2 mx 5 m) in rice fields. 29 days after sowing (in the development stage BBCH 23 of the rice; start of tillering), the spray preparation is applied to the test areas (application with a sprayer). A few days after the treatment, the
  • Echinochloa crus-galli and Brachiaria plantaginea rated in comparison to an untreated control.
  • the active substance preparations are mixed with water.
  • a concentration corresponding to a water application rate of 200 l / ha is set.
  • Rice seeds are sown on trial plots (2 mx 5 m) in rice fields. 29 days after sowing (in the development stage BBCH 23 of the rice; start of tillering), the spray preparation is applied to the test areas (application with a sprayer). A few days after the treatment, the
  • Echinochloa crus-galli and Brachiaria plantaginea rated in comparison to an untreated control.
  • the active substance preparations are mixed with water.
  • a concentration corresponding to a water application rate of 200 l / ha is set.
  • Rice seeds are sown on trial plots (2 mx 5 m) in rice fields. 29 days after sowing (in the development stage BBCH 23 of the rice; start of tillering), the spray preparation is applied to the test areas (application with a backpack sprayer). A few days after the treatment, the
  • Echinochloa crus galli and Brachiaria plantaginea rated in comparison to an untreated control.
  • the active substance preparations are mixed with water.
  • a concentration corresponding to a water application rate of 200 l / ha is set.
  • Rice seeds are sown on trial plots (2 mx 5 m) in rice fields. 18 days after sowing (in the development stage BBCH 12 of the rice; corresponds to the 2-leaf stage), the spray preparation is applied to the test areas (application with a backpack sprayer).
  • the percentage degree of damage to the rice plants or the weed activity on the weeds that have arisen is assessed as Acanthospermum hispidum, Commelina benghalensis, Digitaria sanguinalis and Eleusine indica in comparison to an untreated control.
  • the active substance preparations are mixed with water.
  • a concentration corresponding to a water application rate of 200 l / ha is set.
  • Rice seeds are sown on trial plots (2.5 mx 2.5 m) in rice fields.
  • the spray preparation is applied to the test areas 11 days after sowing (4-leaf stage of the rice) (application with a sprayer). 1 day after the treatment, the soil is dammed up to a water depth of 5 cm; the
  • the active substance preparations are mixed with water.
  • a concentration corresponding to a water application rate of 200 l / ha is set.
  • Rice seeds are sown on trial plots (2.5 mx 2.5 m) in rice fields.
  • the spray preparation is applied to the test areas (application with a backpack sprayer). 2 days after the treatment, the soil is dammed up to a water depth of 5 cm; the
  • the active substance preparations are mixed with water.
  • a concentration corresponding to a water application rate of 200 l / ha is set.
  • Rice seeds are sown on trial plots (2.5 mx 2.5 m) in rice fields. 7 days after sowing (2-leaf stage of the rice), the spray preparation is applied to the test areas (application with a backpack sprayer). 2 days after the treatment, the soil is dammed up to a water depth of 5 cm; the

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  • 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)
EP02792557A 2001-08-30 2002-08-19 Selektive herbizide enthaltend ein tetrazolinon-derivat Withdrawn EP1423010A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10142336 2001-08-30
DE10142336A DE10142336A1 (de) 2001-08-30 2001-08-30 Selektive Herbizide enthaltend ein Tetrazolinon-Derivat
PCT/EP2002/009238 WO2003020035A2 (de) 2001-08-30 2002-08-19 Selektive herbizide enthaltend ein tetrazolinon-derivat

Publications (1)

Publication Number Publication Date
EP1423010A2 true EP1423010A2 (de) 2004-06-02

Family

ID=7697000

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02792557A Withdrawn EP1423010A2 (de) 2001-08-30 2002-08-19 Selektive herbizide enthaltend ein tetrazolinon-derivat

Country Status (15)

Country Link
US (1) US7202196B2 (enExample)
EP (1) EP1423010A2 (enExample)
JP (1) JP2005501876A (enExample)
KR (1) KR20040029033A (enExample)
CN (1) CN1277472C (enExample)
AR (1) AR035286A1 (enExample)
BR (1) BR0212255A (enExample)
CO (1) CO5560518A2 (enExample)
DE (1) DE10142336A1 (enExample)
MX (1) MXPA04001904A (enExample)
MY (1) MY131067A (enExample)
PL (1) PL368852A1 (enExample)
RU (1) RU2004109590A (enExample)
TW (1) TWI254611B (enExample)
WO (1) WO2003020035A2 (enExample)

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CN102228047A (zh) * 2011-05-06 2011-11-02 浙江泰达作物科技有限公司 除草剂苯噻酰草胺与乙氧磺隆复配的水分散性粒剂及其制备方法
CN102228026B (zh) * 2011-05-25 2014-11-12 陕西韦尔奇作物保护有限公司 一种含双草醚与嘧啶氧(硫)苯甲酸酯类的除草组合物
CN103039490B (zh) * 2012-12-26 2015-01-21 山东滨农科技有限公司 一种含有四唑酰草胺和哒草特的除草组合物
CN103636650A (zh) * 2013-10-30 2014-03-19 广东中迅农科股份有限公司 一种含有四唑酰草胺和氯吡嘧磺隆的除草组合物
CN104757013A (zh) * 2015-04-18 2015-07-08 广东中迅农科股份有限公司 含有双唑草腈和四唑酰草胺及精噁唑禾草灵的除草组合物
CN105052980A (zh) * 2015-07-17 2015-11-18 安徽常泰化工有限公司 一种含四唑酰草胺的除草微乳剂
CN106614600B (zh) * 2016-06-26 2019-08-16 江苏中旗科技股份有限公司 一种针对水稻安全的除草组合物

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BR0212255A (pt) 2004-10-19
WO2003020035A2 (de) 2003-03-13
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RU2004109590A (ru) 2005-10-20
JP2005501876A (ja) 2005-01-20
TWI254611B (en) 2006-05-11
CN1575128A (zh) 2005-02-02
KR20040029033A (ko) 2004-04-03
AR035286A1 (es) 2004-05-05
WO2003020035A3 (de) 2003-09-04
DE10142336A1 (de) 2003-03-20
PL368852A1 (en) 2005-04-04
US7202196B2 (en) 2007-04-10
CN1277472C (zh) 2006-10-04
CO5560518A2 (es) 2005-09-30
US20050085388A1 (en) 2005-04-21
MY131067A (en) 2007-07-31

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