WO1998047356A2 - Herbicide - Google Patents

Herbicide Download PDF

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Publication number
WO1998047356A2
WO1998047356A2 PCT/EP1998/002345 EP9802345W WO9847356A2 WO 1998047356 A2 WO1998047356 A2 WO 1998047356A2 EP 9802345 W EP9802345 W EP 9802345W WO 9847356 A2 WO9847356 A2 WO 9847356A2
Authority
WO
WIPO (PCT)
Prior art keywords
formula
herbicide
hydrogen
safener
independently
Prior art date
Application number
PCT/EP1998/002345
Other languages
German (de)
English (en)
Other versions
WO1998047356A3 (fr
Inventor
Reynold Chollet
Original Assignee
Novartis Ag
Novartis-Erfindungen Verwaltungsgesellschaft M.B.H.
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 Novartis Ag, Novartis-Erfindungen Verwaltungsgesellschaft M.B.H. filed Critical Novartis Ag
Priority to AU75278/98A priority Critical patent/AU7527898A/en
Publication of WO1998047356A2 publication Critical patent/WO1998047356A2/fr
Publication of WO1998047356A3 publication Critical patent/WO1998047356A3/fr

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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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system

Definitions

  • the present invention relates to new selective herbicidal compositions for controlling grasses and weeds in crops of useful plants, in particular in crops of maize, sorghum, lawn, sugar cane and cereals, which contain a herbicide and a safener (antidote. Antidote) and which contain the useful plants , but not protect the weeds from the phytotoxic effects of the herbicide, and the use of this agent for weed control in crops.
  • herbicides e.g.
  • the invention thus proposes a selective herbicidal composition which is characterized in that, in addition to customary inert formulation auxiliaries such as carriers, solvents and wetting agents, the active ingredient is a mixture of a) a herbicidally active amount of a compound of the formula I.
  • R 3 is hydrogen, CC 4 alkyl or
  • R 4 and R 5 are independently dC 4 alkyl; or R 4 and R 5 together - (CH 2 ) 4 - or - (CH 2 ) 5 -; R 6 .
  • R, R ⁇ , R 9 , Rio, Rn, R12, R13, R.., Ris. Ri ⁇ , R, Ri ⁇ , R «, R20 and R 21 independently of one another are hydrogen or CC 4 -alkyl; A -CHCI 2 or if R ⁇ (R 2 ) -N- for the group
  • M-, and M 2 independently of one another hydrogen, Na + , K + , 1/2 Mg + , or R22R 2 3R 24 R 2 5N + ;
  • R22, R23, R2 4 , and R 25 independently of one another are hydrogen or CC 4 alkyl and R 6 and R 27 independently of one another are hydrogen or CC 6 alkyl.
  • the compound of formula I is described under the name Dicamba in The Pesticide Manual, 9th Ed., The British Crop Protection Council, pages 245-246.
  • Preferred salts of Compound of formula I are the sodium, potassium, dimethylammonium, trolamine and diglycolamine salts (DGL).
  • DGL diglycolamine salts
  • Compounds of the formula li are described, for example, in US Pat. Nos. 4,971,618, 3,959,304, 4,256,481, 4,601,475, EP 0 149 974, 0 304 409 , EP-A-0 613 618 and DE-OS-2948535.
  • the agents according to the invention preferably contain a compound of the formula II in which Q is Qi, Q or Q 3 . Also preferred are those agents according to the invention in which R T and R 2 together for
  • R 3 is methyl or R 4 and R 5 are methyl and A.
  • CHCI 2 means.
  • Agents according to the invention are also to be emphasized, wherein A for OM 2 and R 1 (R 2 ) -N- for the group
  • K + , 1/2 Mg + , or R 22 R 2 3R 2 2 5N + ; and R 22 , R 23 , R ⁇ , and R 25 independently of one another are hydrogen or dC ⁇ alkyl.
  • the invention also relates to a process for the selective control of weeds in crops, which consists in that the crops, their seeds or cuttings or their cultivated area are treated simultaneously or separately with a herbicidally active amount of the herbicide of the formula I and a herbicidally antagonistically effective amount of the safener of Formula II treated.
  • Suitable crops which can be protected by the safeners of the formula II against the damaging action of the herbicides mentioned above, are, in particular, maize, rice and other types of cereals such as wheat, rye, barley and oats, as well as sugar cane and lawn. Cultures are also to be understood as those which have been made tolerant to herbicides or classes of herbicides by means of conventional breeding or genetic engineering methods.
  • weeds can be both monocot and dicot weeds, such as Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.
  • Stellaria Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanth
  • the cultivated areas are the soil areas already overgrown with the crop plants or filled with the seeds of these crop plants, as well as the soils intended for cultivation with these crop plants.
  • a safener of the formula II can be used for the pretreatment of the seed of the crop (dressing the seed or the cuttings) or can be added to the soil before or after the seed.
  • it can also be applied on its own or together with the herbicide after the plants have emerged.
  • the treatment of the plants or the seed with the safener can therefore in principle be carried out independently of the time of application of the herbicide.
  • the treatment of the plant can also be carried out by simultaneous application of herbicide and safener (for example as a tank mix).
  • the application rate of safener to herbicide largely depends on the type of application.
  • herbicide application rates are generally between 0.001 to 2 kg / ha, but preferably between 0.005 to 1 kg / ha, particularly preferably 40 to 500 g, in particular 100 to 400 g.
  • compositions according to the invention are suitable for all application methods customary in agriculture, such as, for example, pre-emergence application, post-emergence application and seed dressing.
  • the herbicide is preferably applied post-emergent.
  • seed dressing 0.001 to 10 g safener / kg seed, preferably 0.05 to 2 g safener / kg seed, are generally applied. If the safener is applied in liquid form shortly before sowing with seed swelling, then safener solutions are advantageously used which contain the active ingredient in a concentration of 1 to 10,000, preferably 100 to 1000 ppm.
  • the safeners of the formula II or combinations of these safeners with the herbicides of the formula I are expediently used together with those in the Formulation technology processed auxiliaries to formulations, for example, emulsion concentrates, spreadable pastes, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.
  • the formulations are prepared in a known manner, for example by intimately mixing and / or grinding the active ingredients with liquid or solid formulation auxiliaries, such as, for example, solvents or solid carriers.
  • surface-active compounds surfactants
  • surfactants can also be used in the preparation of the formulations.
  • suitable surface-active compounds are nonionic, cationic and / or anionic surfactants and surfactant mixtures with good emulsifying, dispersing and wetting properties.
  • suitable anionic, nonionic and cationic surfactants are listed, for example, in WO 97/34485. Pages 7 and 8.
  • the herbicidal formulations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active compound from the compound of the formula I with the compounds of the formula II, 1 to 99.9% by weight of a solid or liquid formulation aid and 0 to 25% by weight, in particular 0.1 to 25% by weight of a surfactant.
  • concentrated agents are usually preferred as commercial goods, the end user generally uses diluted agents.
  • the agents can also contain further additives such as stabilizers, for example epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, adhesives and fertilizers or other active ingredients.
  • Various methods and techniques can be used for the use of safeners of the formula II or compositions containing them to protect crop plants against the damaging effects of herbicides of the formula, such as, for example, the following: i) seed dressing a) Dressing the seeds with an active ingredient of the formula II formulated as a wettable powder by shaking in a vessel until uniform distribution on the surface of the seeds (dry dressing). About 1 to 500 g of active ingredient of the formula II (4 g to 2 kg of wettable powder) per 100 kg of seed are used. b) dressing the seeds with an emulsion concentrate of the active ingredient of formula II according to method a) (wet dressing). c) dressing by immersing the seeds in a broth with 100-1000 ppm of active ingredient of the formula II for 1 to 72 hours and, if appropriate, subsequently drying the seeds (immersion dressing).
  • the dressing of the seeds or the treatment of the germinated seedlings are naturally the preferred methods of application because the treatment of the active ingredient is completely aimed at the target culture.
  • 1 to 1000 g antidote, preferably 5 to 250 g antidote, are used per 100 kg of seed, depending on the method, which also allows the addition of other active substances or micronutrients, to deviate upwards or downwards from the specified limit concentrations ( Repetitive stain), ii) Application as a tank mix
  • the safener is introduced into the open seeded furrow as an emulsion concentrate, wettable powder or as granules. After covering the furrow, the herbicide is applied in the pre-run procedure in the usual way. iv) Deliver controlled active ingredient
  • the active ingredient of formula II is applied in solution to mineral granulate carriers or polymerized granules (urea / formaldehyde) and dried. If necessary, a coating can be applied (coating granules), which allows the active ingredient to be dispensed in doses over a certain period of time.
  • Active substance mixture 0.1 to 10%, preferably 0.1 to 5% solid carrier: 99.9 to 90%, preferably 99.9 to 99%.
  • Suspension concentrates Active substance mixture: 5 to 75%, preferably 10 to 50 % Water: 94 to 24%, preferably 88 to 30% surfactant: 1 to 40%, preferably 2 to 30% wettable powders: active ingredient mixture: 0.5 to 90%, preferably 1 to 80% surfactant: 0.5 to 20%, preferably 1 to 15% solid carrier material: 5 to 95%, preferably 15 to 90%
  • Active ingredient mixture 0.1 to 30%, preferably 0.1 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%
  • Active ingredient mixture I + II 10% 50% 90% 1-methoxy-3- (3-methoxy-propoxy) propane - 20% 20%
  • the solutions are suitable for use in the form of tiny drops.
  • the active ingredient is mixed well with the additives and ground well in a suitable grinder.
  • Spray powders are obtained which can be diluted with water to form suspensions of any desired concentration.
  • the active ingredient is dissolved in methylene chloride, sprayed onto the carrier and that
  • Active ingredient mixture I + II 0.1% 5% 15%
  • Polyethylene glycol MG 200 1.0% 2% 3%
  • the finely ground active ingredient is evenly applied in a mixer to the carrier material moistened with polyethylene glycol. In this way, dust-free coating granules are obtained.
  • the active ingredient is mixed with the additives, ground and moistened with water. This mixture is extruded and then dried in an air stream.
  • Ready-to-use dusts are obtained by mixing the active ingredient with the carrier substances and grinding them in a suitable mill.
  • the finely ground active ingredient is intimately mixed with the additives. You get one
  • Suspension concentrate from which, by dilution with water, suspensions each desired concentration can be produced. It is often more practical to individually formulate the active ingredient of formula I and the mixing partner of formula II and then to bring them together in the desired mixing ratio as "tank mix" in water shortly before application in the applicator.
  • the ability of the safeners of the formula II to protect crop plants from the phytotoxic action of herbicides of the formula I is illustrated in the following example.
  • Example B1 Post-emergent phytotoxic effects of the herbicide of the formula I and the mixtures of herbicide with safener of the formula II on maize: Under greenhouse conditions, maize is grown in plastic pots up to the 2-3 leaf stage. At this stage, on the one hand be the herbicide of formula I (BANVEL ® 480 SL, corresponds to 480 g of active substance / I) applied as a dimethylammonium salt alone and the mixtures of the herbicide with the safener no. 1:05 from Table 1 on the test plants. Application is carried out as an aqueous suspension of the test substances (compound no. 1.05 formulated according to Example F3), each with 600 l of water / ha.
  • the test substances compound no. 1.05 formulated according to Example F3
  • the concentration of herbicide is 2.4 I / ha, the concentration of safener 125g / ha. 33 days after application, evaluation is carried out on a scale which comprises values from 0 to 4. 4 means test plant has died, 2 means medium effect, 0 means no phytotoxic effect.
  • Table B1 show that the safener No. 1.05 in Table 1 can significantly reduce the damage to maize caused by the herbicide of the formula I.
  • Table B1 Post-emergent phytotoxic effects of the herbicide of the formula I and the mixtures of herbicide with safener of the formula II on maize:

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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)

Abstract

La présente invention concerne un agent herbicide sélectif pour éliminer herbes et mauvaises herbes dans les cultures de plantes utiles, contenant a) une quantité suffisante d'un composé de la formule (I) et de ses sels pour lui conférer des propriétés herbicides; et b) une quantité suffisante d'un phytoprotecteur de la formule (II) pour lui conférer des propriétés anti-herbicides, formule (II) dans laquelle R1, R2 et A ont la signification indiquée dans la revendication 1.
PCT/EP1998/002345 1997-04-23 1998-04-21 Herbicide WO1998047356A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU75278/98A AU7527898A (en) 1997-04-23 1998-04-21 Herbicide

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH95297 1997-04-23
CH952/97 1997-04-23
CH2426/97 1997-10-20
CH242697 1997-10-20

Publications (2)

Publication Number Publication Date
WO1998047356A2 true WO1998047356A2 (fr) 1998-10-29
WO1998047356A3 WO1998047356A3 (fr) 1999-03-11

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ID=25686201

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/002345 WO1998047356A2 (fr) 1997-04-23 1998-04-21 Herbicide

Country Status (2)

Country Link
AU (1) AU7527898A (fr)
WO (1) WO1998047356A2 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002100171A1 (fr) * 2001-06-13 2002-12-19 Syngenta Participations Ag Composition herbicide
WO2003103394A2 (fr) * 2002-06-08 2003-12-18 Bayer Cropscience Gmbh Combinaisons d'acides carboxyliques aromatiques herbicides et de phytoprotecteurs
US7910149B2 (en) 2001-11-05 2011-03-22 Danisco A/S Liquid bread improver, the use and the process for producing thereof
US9867376B2 (en) 2012-05-24 2018-01-16 Bayer Cropscience Ag Herbicidal compositions comprising N-tetrazol-5-yl)- or N-(triazol-5-yl)arylcarboxamides
US10111435B2 (en) 2013-10-25 2018-10-30 Bayer Cropscience Aktiengesellschaft Herbicidal compositions containing N-(1,3,4-oxadiazol-2-yl)-aryl carboxylic acid amides
US10258044B2 (en) 2013-08-09 2019-04-16 Bayer Cropscience Aktiengesellschaft Ternary herbicide combinations
USRE47666E1 (en) 2008-02-21 2019-10-29 Bayer Cropscience Aktiengesellschaft Herbicidal compositions

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0304409A1 (fr) * 1987-08-13 1989-02-22 Monsanto Company Oxazolidinehalogénoacétamides substitués en position 5 par un groupe hétérocyclique
EP0354201A2 (fr) * 1988-08-01 1990-02-07 Monsanto Company Antidotes pour des dérivés herbicides de l'acide benzoîque
EP0480902A1 (fr) * 1990-10-12 1992-04-15 Monsanto Company Antidotes pour des dérivés herbicides de l'acide benzoique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0304409A1 (fr) * 1987-08-13 1989-02-22 Monsanto Company Oxazolidinehalogénoacétamides substitués en position 5 par un groupe hétérocyclique
EP0354201A2 (fr) * 1988-08-01 1990-02-07 Monsanto Company Antidotes pour des dérivés herbicides de l'acide benzoîque
EP0480902A1 (fr) * 1990-10-12 1992-04-15 Monsanto Company Antidotes pour des dérivés herbicides de l'acide benzoique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 124, no. 25, 17.Juni 1996 Columbus, Ohio, US; abstract no. 335531, D.L.KUNKEL ET AL.: "Safeners reduce corn (Zea mays) chloroacetanilide and dicamba injury under different soil temperatures" XP002076017 & WEED TECHNOL., Bd. 10, Nr. 1, 1996, Seiten 115-120, *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002100171A1 (fr) * 2001-06-13 2002-12-19 Syngenta Participations Ag Composition herbicide
US7910149B2 (en) 2001-11-05 2011-03-22 Danisco A/S Liquid bread improver, the use and the process for producing thereof
WO2003103394A2 (fr) * 2002-06-08 2003-12-18 Bayer Cropscience Gmbh Combinaisons d'acides carboxyliques aromatiques herbicides et de phytoprotecteurs
WO2003103394A3 (fr) * 2002-06-08 2004-02-12 Bayer Cropscience Gmbh Combinaisons d'acides carboxyliques aromatiques herbicides et de phytoprotecteurs
US6887827B2 (en) 2002-06-08 2005-05-03 Bayer Cropscience Gmbh Combinations of herbicidal aromatic carboxylic acids and safeners
USRE47666E1 (en) 2008-02-21 2019-10-29 Bayer Cropscience Aktiengesellschaft Herbicidal compositions
US9867376B2 (en) 2012-05-24 2018-01-16 Bayer Cropscience Ag Herbicidal compositions comprising N-tetrazol-5-yl)- or N-(triazol-5-yl)arylcarboxamides
US10258044B2 (en) 2013-08-09 2019-04-16 Bayer Cropscience Aktiengesellschaft Ternary herbicide combinations
US11291208B2 (en) 2013-08-09 2022-04-05 Bayer Cropscience Aktiengesellschaft Ternary herbicide combinations
US10111435B2 (en) 2013-10-25 2018-10-30 Bayer Cropscience Aktiengesellschaft Herbicidal compositions containing N-(1,3,4-oxadiazol-2-yl)-aryl carboxylic acid amides

Also Published As

Publication number Publication date
AU7527898A (en) 1998-11-13
WO1998047356A3 (fr) 1999-03-11

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