TW201715968A - Herbicidal compositions comprising N-(tetrazole-5-yl)- or N-(1,3,4- oxadiazole-2-yl)aryl amides and an 3-isoxazolidinone derivative - Google Patents

Abstract

A description is given of herbicidal compositions comprising N-(tetrazole-5-yl)- or N-(1,3,4- oxadiazole-2-yl)aryl amides and an 3-isoxazolidinone. These herbicidal compositions are particularly suitable for use against weed plants in crops of useful plants.

Description

Herbicidal composition comprising N-(tetrazol-5-yl)- or N-(1,3,4-oxadiazol-2-yl)aryl decylamine and 3-isoxolinone derivative

The present invention relates to agrochemically active herbicidal compositions and to their use for controlling weed plants.

WO 2012/028579 A1 and WO 2012/126932 A1 disclose herbicidal active N-(tetrazol-5-yl)- and N-(1,3,4- Diazol-2-yl) aryl decylamine. Herbicidal compositions of the above-mentioned compounds with other herbicidal active compounds are disclosed in WO 2013/174845 A1 and WO 2015/059187 A1. US 4,405,357 A1 discloses certain 3-dimers as herbicides used under pre-emergence conditions Oxazolinone derivatives.

However, the herbicidal compositions and compounds mentioned above do not always have sufficient activity against harmful plants and/or some cannot always be applied under pre-emergence and post-emergence conditions.

Accordingly, it is an object of the present invention to provide herbicidal compositions having improved properties. This object is achieved by the herbicidal composition of the invention described below and which comprises certain N-(tetrazol-5-yl)- or N-(1,3,4- Diazol-2-yl)aryl decylamine and 3-iso Oxazolinone derivatives.

Accordingly, the present invention provides a herbicidal composition comprising: Component A and Component B, wherein component A is selected from the group consisting of A1 2-chloro-4-methyl-3-(methylsulfonyl) -N-(1-methyl-1H-tetrazol-5-yl)benzamide, A2 2,4-dimethyl-3-(methylsulfonyl)-N-(1-methyl- 1H-tetrazol-5-yl)benzamide, A3 4-ethyl-2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazole-5- Benzomethane, A4 2-chloro-3-(methylthio)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide Amine, A5 2-methyl-N-(5-methyl-1,3,4- Diazol-2-yl)-3-(methylsulfonyl)-4-(trifluoromethyl)benzamide and A6 2-chloro-N-(5-methyl-1,3,4- Dioxazol-2-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide, and component B is 2-(2,4-dichlorophenyl)methyl Base-4,4-dimethyl-3-iso Oxazolone: A1: 2-Chloro-4-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)benzamide

A2: 2,4-dimethyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)benzamide

A3: 4-ethyl-2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)benzamide

A4: 2-Chloro-3-(methylthio)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide

A5: 2-methyl-N-(5-methyl-1,3,4- Diazol-2-yl)-3-(methylsulfonyl)-4-(trifluoromethyl)benzamide

A6: 2-chloro-N-(5-methyl-1,3,4- Diazol-2-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide

B: 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-iso Oxazolone

The herbicidal compositions of the present invention may comprise other ingredients or be used with other ingredients, examples being other types of active crop protection ingredients and/or adjuvants and/or formulation aids conventionally used in crop protection.

Surprisingly, the herbicidal compositions of the present invention not only exhibit synergistic effects on unwanted weed plants, but additionally exhibit other special qualities: for example, they can be applied to crops of useful plants over a wide time window to counter unwanted Grass plants without significant damage to useful plants. Another unexpected effect is the fact that the herbicidal compositions of the present invention show synergistic effects on weed plants that have developed resistance to HPPD inhibitors.

The herbicidal compositions of the present invention can be applied to, for example, plants, plant parts or plant seeds or areas on which plants are grown, such as, for example, together (e.g., in co-formulation or in barrels), in a manner known to those skilled in the art. The mixture is applied or applied in a short time (separate) from each other. For example, the individual active ingredients may be applied or the herbicidal compositions may be applied in two or more portions (sequentially applied), for example after application before pre-emergence, followed by post-emergence application; or after early application after germination, followed by mid- or late-stage germination Applied in the later period. Preferably, components A and B are applied in combination or near synchronously. It is also preferred to apply from pre-emergence to early post-emergence.

In the herbicidal composition of the present invention, the application rate of component A is usually from 5 g to 250 g of activity. Ingredients (a.i.)/ha, preferably 10g to 150g a.i./ha, especially preferably 10g to 100g a.i./ha. The application rate of component B is usually from 25 g to 750 g of active ingredient per hectare, preferably from 25 g to 500 g a.i./ha, especially preferably from 50 g to 375 g a.i./ha.

The synergistic effect of the herbicidal compositions of the invention is particularly pronounced at certain concentration ratios. However, the weight ratio of components A and B can vary over a relatively wide range. In general, component A of from 1:150 to 10:1 parts by weight, preferably from 1:50 to 6:1 parts by weight, particularly preferably from 1:37.5 to 2:1, is present per part by weight of component B.

When the herbicidal compositions of the present invention are used, very broad spectrum weed plants are controlled before and after emergence, examples being annual and perennial monocotyledonous or dicotyledonous weeds and unwanted crop plants. The herbicidal compositions of the present invention are particularly useful in crops such as cereals, corn, rice, soybeans, canola, sugar beets, cotton, and sugar cane, and are suitable for use in long-term crops on plantations and non-cultivated land. It is preferred for use in crops of cereals, corn, cotton and soybeans. It is also highly suitable for use in genetically modified crops of corn, cotton and soybeans.

The invention accordingly further provides a method for controlling weed plants in a plant crop, characterized in that components A and B of the herbicidal composition of the invention are applied to plants (for example weed plants, such as monocotyledonous or dicotyledonous weeds) Or unwanted crop plants) or applied to the area on which the plants are grown, this application is carried out, for example, jointly or separately.

Monocotyledonous weeds are from the following genera: for example, Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa , Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, sorghum Genus (Sorghum), Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Valerian ( Scirpus), Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Phalaris. Dicotyledonous weeds are from the following genera: for example, Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis , Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus Genus (Convolvulus), Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus ), Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon , Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus Ranunculus), Taraxacum, Euphorbia.

The invention also provides the use of the herbicidal compositions of the invention for controlling the growth of weed plants in preferred crops such as cereals, corn, cotton and soybeans.

The herbicidal compositions of the present invention can be produced by known methods, for example, in the form of a mixture of individual components as appropriate with other active ingredients, adjuvants and/or conventional formulation aids, and then the compositions are conventionally used ( For example, a water dilution can be used; or it can be produced by separately mixing or partially dispersing the individual components by a combined dilution with water in the form of a mixture of barrels. Likewise, individual components that are separately or partially dispensed may be applied by time offset (separate application). Another possibility is to apply the individual components or to apply the herbicidal composition in two or more portions (sequential application), such as, for example, after pre-emergence application, followed by post-emergence application; or after early post-emergence application, It is then applied in the middle or late stages of the late stage. Preferred herein are the combination of active ingredients in combination or near simultaneous application of the respective combinations.

The herbicidal compositions of the present invention can also be used to control weed plants in crops of genetically modified plants that are known or not yet developed.

In general, transgenic plants are notable for their particular beneficial properties, such as resistance to certain pesticides, especially certain herbicides; to plant diseases or organisms that cause plant diseases (eg certain insects or microorganisms, such as fungi, Resistance to bacteria or viruses). Other special properties relate to, for example, the quantity, quality, storage, composition and specific ingredients of the harvest. For example, transgenic plants having elevated starch content or altered starch quality or having different fatty acid compositions are known in the harvest. Other specific properties may be tolerance or resistance to abiotic sources of pressure such as heat, low temperature, drought, salinity, and ultraviolet radiation.

Conventional methods of producing new plants having altered properties compared to plants present to date involve, for example, traditional breeding methods and the production of mutants. Alternatively, new plants having altered properties can be produced by means of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, the following various descriptions exist:

- genetic modification of crop plants for the purpose of altering the starch synthesized in plants (eg WO 92/11376, WO 92/14827, WO 91/19806)

- against glufosinate type (Ref., for example, EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or sulfonylurea type (EP-A-0257993, US-A-5013659 Specific herbicide-to-transgenic crop plants

- Transgenic crop plants (eg cotton) capable of producing Bacillus thuringiensis toxin (Bt toxin), which enable plants to fight against specific pests (EP-A-0142924, EP-A-0193259)

- GM crop plants with altered fatty acid composition (WO 91/13972)

- genetically modified crop plants with new plant components or secondary metabolites (eg new plant defensins that cause increased disease resistance) (EPA 309862, EPA0464461)

- genetically modified plants with reduced light respiration characterized by higher yield and higher stress tolerance (EPA 0305398)

- GM crop plants that produce medicinal or diagnostically important proteins ("pharming")

- GM crop plants characterized by higher yield or better quality

- GM crop plants ("gene stacks") characterized by, for example, a combination of the above new properties.

A variety of molecular biology techniques by which new transgenic plants with altered properties can be produced are known in principle; see, for example, I. Potrykus and G. Spangenberg (ed.), Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg. or Christou, "Trends in Plant Science" 1 (1996) 423-431).

For such recombination operations, nucleic acid molecules that permit mutagenesis or sequence alteration by recombination of the DNA sequence can be introduced into the plastid. Base exchange, removal of portions of the sequence or addition of natural or synthetic sequences can be performed, for example, by standard methods. For ligation of DNA fragments to each other, a adaptor or linker can be attached to the fragment; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor , NY; or Winnacker "Gene und Klone" [Genes and Clones], VCH Weinheim, 2nd edition, 1996.

For example, a plant cell having reduced gene product activity can be produced by expressing at least one corresponding antisense RNA, sense RNA for achieving a co-repressor effect, or by expressing at least one transcript that specifically cleaves the above gene product It is achieved by a suitable ribozyme.

For this purpose, DNA molecules encompassing the entire coding sequence of the gene product (including any flanking sequences that may be present), and DNA molecules covering only portions of the coding sequence, which must be sufficiently long to have antisense in the cell, may be used first. effect. DNA sequences that are highly homologous to, but not identical to, the coding sequence of the gene product can also be used.

When a nucleic acid molecule is expressed in a plant, the synthesized protein can be located in any desired compartment of the plant cell. However, in order to achieve a position in a particular compartment, it can, for example, be compiled The code region is linked to a DNA sequence that ensures localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al, EMBO J. 11 (1992), 3219-3227; Wolter et al, Proc. Natl. Acad. Sci. USA 85 (1988). , 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Nucleic acid molecules can also be expressed in organelles of plant cells.

Transgenic plant cells can be regenerated by known techniques to produce whole plants. In principle, the transgenic plant can be a plant of any desired plant species, ie both monocotyledonous and dicotyledonous plants.

For example, transgenic plants can be obtained that alter properties by overexpression (repression or inhibition) of homologous (ie, native) genes or gene sequences or by expression of heterologous (ie, foreign) genes or gene sequences.

Preferably, the composition of the invention is useful for combating growth regulators (such as dicamba) or against inhibition of essential plant enzymes (eg, acetaminolate synthase (ALS), EPSP synthase, glutamate synthase (GS) Or a hydroxyphenylpyruvate dioxygenase (HPPD) herbicide or against sulfonylurea, glyphosate, glufosinate or benzamidine A transgenic crop of herbicide and a group of similar active ingredients.

When the compositions of the invention are used in transgenic crops, the effects observed on other weed plants in the crops are also often accompanied by the application of specific effects in particular transgenic crops, such as altered or specific broadening of the controllable miscellaneous The grass spectrum, the altered application rate that can be applied, preferably the good combination with the herbicides that the GM crop can combat, and the growth and yield of the GM crop plants.

Accordingly, the invention also provides the use of a composition of the invention for controlling weed plants in transgenic crop plants.

Preferred are the use of the compositions of the present invention in transgenic crops of economic importance for plants and ornamental plants, such as cereals (eg, wheat, barley, rye, oats), alfalfa/sorghum, rice, cassava And corn, or beets, cotton, large Crops of beans, canola, potatoes, tomatoes, peas and other vegetable crops, especially in corn, cotton and soybeans.

Accordingly, the present invention also provides the use of a composition of the invention for controlling a weed plant in a transgenic crop plant or a tolerant crop plant during selective breeding.

Components A and B can be converted together or separately into, for example, conventional formulations applied by spraying, irrigation, and spraying, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, actives Microcapsules in natural and synthetic substances and polymeric substances impregnated with ingredients. Formulations may contain conventional adjuvants and adjuvants.

Such formulations are produced in a known manner, for example, by using surfactants (i.e., emulsifiers and/or dispersants and/or foam formers), as appropriate, with components A and B and extenders (ie, The liquid solvent, pressurized liquefied gas and/or solid carrier are mixed.

If the extender used is water, it is also possible to use, for example, an organic solvent as an auxiliary solvent. Useful liquid solvents are: aromatic, such as xylene, toluene or alkylnaphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride or dichloromethane; aliphatic hydrocarbons such as rings Hexane or paraffin, such as petroleum fractions, mineral oils and vegetable oils; alcohols such as butanol or ethylene glycol and ethers and their esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexane Ketone; a strong polar solvent such as dimethylformamide or dimethylhydrazine and water.

Useful solid carriers include, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, magnesium aluminum sepiolite, montmorillonite or diatomaceous earth, and ground synthetic minerals, for example Fine cerium oxide, aluminum oxide and cerium salt; useful solid carriers for granules include, for example, pulverized and graded natural rock such as calcite, marble, pumice, sepiolite, dolomite and inorganic and organic powders. Granules of synthetic particles and organic materials (such as sawdust, coconut shells, corn cobs and tobacco stems); emulsifiers and/or foam formers include, for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxygen Ethylene fatty alcohol ethers, such as alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, and protein hydrolysates; useful dispersing agents include, for example, lignin Sulfite waste liquid and methyl cellulose.

In such formulations, tackifiers such as carboxymethylcellulose; natural and synthetic polymers in powder, granule or latex form, such as acacia, polyvinyl alcohol and polyvinyl acetate; or natural phospholipids may be used. For example, cephalin and lecithin and synthetic phospholipids. Other additives may be mineral oils and vegetable oils.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and Prussian Blue; and organic dyes such as valerin dyes, azo dyes and metal anthraquinone dyes; and trace nutrients such as iron, may be used. Salts of manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations typically contain between 0.1% and 95% by weight of components A and B, preferably between 0.5% and 90% by weight.

Components A and B (either by themselves or in their formulation) may also be used as a mixture with other agrochemical active ingredients used to control unwanted plant growth, for example to control weeds or to control unwanted crop plants. For example, a finished formulation or a barrel mix is possible.

It may also be associated with other known active ingredients (eg fungicides, insecticides, acaricides, nematicides, avian antifeedants, phytonutrients and soil amendments) and the same adjuvants used in crop protection and Mixture of formulation aids.

The components A and B can be used as such, in the form of their formulations or by further dilution of the use forms prepared therefrom, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. Typically, application is accomplished by, for example, irrigation, spraying, spraying, spreading.

Components A and B can be applied to plants, plant parts or cultivated areas (farm), preferably green plants and plant parts, and on farmland. One method of application is by co-administering the active ingredient in the form of a barrel mixture by mixing the optimally formulated concentrated active ingredient with water in a bucket and applying the resulting spray solution.

For application, the formulation that will exist in commercial form is diluted as usual in the usual way. The release is, for example, diluted with water in the case of a wettable powder, an emulsifiable concentrate, a dispersion and water-dispersible granules. Formulations in the form of powders, granules for soil application or granules for spreading and sprayable solutions are generally not further diluted prior to application by the use of other inert materials.

Biological instance Example A Pre-emergence herbicidal action against weed plants

Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are sown in sandy loam in wood fiber tanks and covered with soil. The herbicidal composition of the present invention formulated as a wettable powder (WP) or an emulsifiable concentrate (EC) is then applied to the surface of the cover soil in the form of an aqueous suspension or emulsion at a water application rate of 300 l/ha or At the time of conversion, it is from 600 l/ha to 800 l/ha, and 0.2% of a wetting agent is added. After treatment, the cans were placed in a greenhouse and maintained under good growth conditions of the test plants. Visual assessment of damage to test plants compared to untreated controls after 28 days of test time (% herbicidal activity (%): 100% activity = plant dead; 0% activity = same as control plants). The data is listed in the table below. The data reveals the synergistic effect of the herbicidal compositions of the invention on several weeds.

The meaning of the abbreviation is as follows:

E ^C = according to the expected value of Colby (E ^C =A+BA×B/100)

Δ = the difference between the measured value and the expected value (%) (measured value minus expected value)

Evaluation:

- The measured value E is greater than E ^C :-> synergy (+△)

- the measured value E is equal to E ^C :-> cumulative effect

- Measured value E is less than E ^C :-> antagonism (-△)

POLCO stalk stalk (Polygonum convolvulus)

Instance B Post-emergence weeding effect on weed plants

Seeds of monocotyledonous and dicotyledonous weeds and crop plants are placed in sandy loam in wood fiber tanks, covered with soil and cultivated under good growth conditions in a greenhouse. Test plants were treated at one leaf stage 2 to 3 weeks after sowing. Then, the herbicidal composition of the present invention formulated in the form of wettable powder (WP) or emulsion concentrate (EC) is sprayed on the green portion of the plant in the form of an aqueous suspension or emulsion at a water application rate of 300 l/ha or 600 l. /ha to 800 l/ha (converted) and added 0.2% wetting agent. After allowing the test plants to stand in the greenhouse under optimal growth conditions for about 3 to 28 days, the effect of the formulation was evaluated visually compared to the untreated control (% herbicidal effect (%): 100% activity = plant died , 0% activity = as control plants). The data reveals the synergistic effect of the herbicidal compositions of the invention against several weeds.

Claims (15)

A herbicidal composition comprising component A and component B, wherein component A is selected from the group consisting of A1 2-chloro-4-methyl-3-(methylsulfonyl)-N-( 1-methyl-1H-tetrazol-5-yl)benzamide, A2 2,4-dimethyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazole -5-yl)benzamide, A3 4-ethyl-2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)benzene Indoleamine, A4 2-chloro-3-(methylthio)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide, A5 2 -methyl-N-(5-methyl-1,3,4- Diazol-2-yl)-3-(methylsulfonyl)-4-(trifluoromethyl)benzamide, and A6 2-chloro-N-(5-methyl-1,3,4 - Dioxazol-2-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide, and component B is 2-(2,4-dichlorophenyl)methyl Base-4,4-dimethyl-3-iso Oxazolone. The herbicidal composition of claim 1, which comprises component A and component B in a weight ratio of 1:150 to 10:1. The herbicidal composition of claim 1, which comprises component A and component B in a weight ratio of 1:50 to 6:1. The herbicidal composition of claim 1, which comprises component A and component B in a weight ratio of 1:37.5 to 2:1. A method for controlling weed plants in crops of useful plants, characterized in that the herbicidal composition according to claim 1 is applied to the weed plants, plants or plants Seeds or applied to the area on which the weed plants grow. The method of claim 5, wherein the crops are from a population consisting of cereals, corn, cotton, and soybeans. The method of claim 5, wherein the crops have been genetically engineered. The method of claim 5, wherein the method is performed pre-emergence or early post-emergence. The method of claim 5, wherein the method is practiced to control HPPD resistant weed plants. A use of the herbicidal composition of claim 1 for controlling weed plants in a crop. The use of claim 10, wherein the crops are from a population consisting of cereals, corn, cotton, and soybeans. As used in claim 10, it is used to control weed plants from a population of HPPD resistant plants. The use of claim 10, wherein component A is used at an application rate of from 5 g/ha to 200 g/ha, and component B is used at an application rate of from 25 g/ha to 750 g/ha. The use of claim 13, wherein component A is used at an application rate of from 10 g/ha to 150 g/ha, and component B is used at an application rate of from 25 g/ha to 500 g/ha. The use of claim 13, wherein component A is used at an application rate of from 10 g/ha to 100 g/ha, and component B is used at an application rate of from 50 g/ha to 375 g/ha.