BR102014031833A2 - use of compounds of formula i, method for combating rust, seed, compounds of formula i and agrochemical compositions - Google Patents

Abstract

use of the compounds of formula I, method for combating rust, seed, compounds of formula I and agrochemical compositions. It is used to combat the phytopathogenic rust of soybean and seeds coated with (2e) -2-methoximino-2- [2 - [[(e) - [(2e) -2-alkoxyimin-1-methyl-alk -3-enylidene] amino] oxymethyl] phenyl] -N-methylacetamides. The invention also relates to methods for combating soybean rust (a disease caused by phakopsora pachyrhizi and P. meibomiae) comprising treating soybean plants or seeds to be protected against attacks by the phakopsora pachyrhizi and p meibomiae fungi. The invention also relates to novel compounds of (2e) -2-methoxyimino-2- [2 - [[(e) - [(2e) -2-alkoxyimin-1-methyl-aic-3-enylidene] amino ] oxymethyl] phenyl] n-methyl acetamide.

Description

USE OF FORMULA F COMPOUNDS, METHOD FOR COMBATING RUST. SEED, FORMULA COMPOUNDS AND AGROCHEMICAL COMPOSITIONS ”Description [001] The present invention relates to the use of (2 £} -2-methoxyimin-2- [2 - [[(E) - [(2 £) -2- alkoxyimino-1-methyl-alk-3-enylidene] amino] oxymethyl] -phenyl] -Î ”/ methyl acetamides to combat soybean phytopathogenic rust and (2E) -2-methoxy-2-coated seeds [2 - [[(EH (2E) -2-Alkoxyimin-1-methth-alk-3-enylidene] amino] oxymethylHenyl] -α / methyl-acetamides The invention also relates to methods for combating soybean rust (a disease caused by Phakopsora pachyrhizí and P. meibomiae) comprising treating soybean plants or seeds to be protected against the attack of the Phakopsora pachyrhizí and P. meibomiae fungi. The invention also relates to novel compounds of (2 £} -2-Methoxyimino-2- [2 - [[(E) - [(2E) -2-alkoxyimin-1-methyl-alk-3-enidene-jaminooxymethyl] -phenyl] -Î ”-methyl-acetamide; gives.

Soybean rust is a serious vegetable disease, particularly to soybean plants. caused by the basidiomycete fungi. pathogenic to plants, Phakopsora pachyrhizí and P meibomiae. P pachy-rhizi originated in Asia. so it is also called the causal agent of Asian soybean rust, whereas the less aggressive P meibomiae species originated in Latin America. Among the New World countries, the R pachyrhizí had its arrival first reported in the 1990s upon reaching Hawaii and. since 2001. has been detected in South America (Mol Pfant Pathoi 11 (2), pages 169 to 177, 2010). Soybean rust is spread by windblown spores and has caused significant planting losses in many regions of the world developing soybean (http://www.ppdt.purdue.edu/ppdl/SQvbean rust.html).

WQ 95/021154 generally mentions derivatives of phenyl acetic acid of generic formula: and their use for fungicidal use against certain plant pathogenic fungi. However, VVO 95/021154 does not disclose any actions against soybean rust nor does it specifically mention in that document the (2E) -2-methoximino-2- [2-thi (E) - [(2E) -2-alkoxyimin-1 -methyl "C1 -C3 -enylidene] amino] oxymethyl] -phenyl] - N -methyl [-acetamides according to this invention.

The use of certain strobilurin-like compounds to combat soybean rust is known from WO 11/095134, among others. The compounds according to the present invention differ from those described in VVO 11/095134, inter alia, by the oximaether double specific secondary chain and the phenyl-2-methoximino-N-methyl pharmacophoric acetamide as defined herein.

[005] In many cases, particularly at low application rates, the fungicidal activity of known fungicidal compounds, especially against soybean rust, is unsatisfactory. Based on this, it is an object of the present invention to provide a use for soybean rust control with compounds which have an improved activity against soybean rust caused by the fungi Phakopsora pachyrhizi and P meibomiae.

[006] This object is achieved using (2E) -2-methoximino-2- [2 - [[(E) - [(2E) -2 "alkoxy-1-met-yl-alk-3-enylidene ] amino] oxymethyl] -phenii] - / V-methyl acetamides against soybean rust disease caused by Phakopsora pachyrhizi and P meibomiae.

[007] Accordingly. The present invention relates to the use of the compound of formula I: wherein R is hydrogen, halogen or methyl; R, R * are independently selected from hydrogen. C 1 -C 4 is C 1 -C 4 halo and C 1 -C 6 haloalkyl: or R 1 and R 2 together with the carbon atom linking them forms C 5 -C 8 cycloalkyl; R3 is C1 -C6 alkyl; to combat soybean rust, The term "compounds" refers to compounds of Formula I, An additional embodiment refers to the use of compounds 1 to combat soybean rust in soybean plants and in the material of plant propagation such as seeds and the planting material of these plants Soybean rust is caused by fungal pathogens called Phakopsora pachyrhizi and P. meibomiae.

Accordingly, the further embodiment relates to the use of compounds 1 to combat Phakopsora pachyrhizi and / or P meibomiae in soybean plants and plant propagating material, such as seeds, and the planting material of such plants. A more preferred embodiment of the use of t-compounds to combat Phakopsora pachyrhizi in soybean plants and in plant propagation material, such as: As seeds, and in the planting material of such plants refers accordingly, the present invention relates to the method for combating soybean rust (Phakopsora pachyrhizi and / or P, meibomiae). which comprises treating the soybean plants or soybean propagating material to be protected against attack by Phakopsora pachyrhizi and / or P meibomiae with an effective amount of at least one t-compound or a composition comprising such compound I.

[012] Treatment against soybean rust may be preventative or curative.

Preferably, the treatment of soybean plants against soybean rust is preventive. Preventive treatment is effective when soybean plants are at risk of fire infection at the latest after the first symptoms become visible. According to one embodiment, the first treatment of soybean plants occurs from the vegetative growth stages V3 to V4 (which means four fully extended trifoliate eyes) to the reproductive growth stage R2 (in full bloom), most preferably. It occurs from the vegetative growth stages V6 to V8 (meaning from δ to 8 fully extended trifoliate leaves) to the reproductive growth stage R1 (at the beginning of flowering). Depending on the pressure of the disease two to four applications can be used e. In extreme conditions, up to five applications may be required at intervals of 10 to 21 days between applications.

[014] In use as a foliar sprinkler against soybean rust. The amounts of the compounds 1 applied are, depending on the specific compound used and the pressure of the disease, 5 g to 500 g per ha, preferably 10 to 200 g per ha, more preferably 25 to 125 g per ha and in particular 30 g. at 80 g per ha.

The preparation of a compound of Formula I, (2E) -2-methoxyimino-2- [2 - [[((R) -f (2 R) -2-methoxyimin-1,4-dimethyl-pent-3 -enylidene] amino] axymethyl] methylen] - [N-methyl acetamide] is disclosed in WO 00/0311023. However, it does not mention that this compound, among others, can be used to combat soybean rust.

[016] The compounds according to the present invention differ from those described in the mentioned publication in which (2F) -2-methoxymine-2- [2-f [(E) - [(2E) -2-methoximino-1, 4-dimety-pent-3-enylidene] amino] oxymethyl] phenyl] -A / methyl acetamide is excluded, Accordingly, in accordance with a further aspect, the invention provides the compounds of Formula 1 which are represented by wherein R is hydrogen, halogen or methyl; R, R "are independently selected from hydrogen. C 1 -C 4 -quififa and O-Cc-haloalkyl; or R 1 and together with the carbon atom linking them form the C 1 -C 6 cycloalkyl; R 3 is C 1 -C 4 alkyl, except for (2F) -2-methoxyimino-2- [2 - [[(E) - [(2E) -2-methoxyimino-1,4-dimethyl-pent-3-en-ylidene ] amino] oxymethyl] -phenyl] -Î ± -methylhacetamide.

[018] Compounds I may be present in atropoisomers that appear from the restricted gyrus around a single bond of asymmetric groups. They also form part of the subject matter of the present invention.

Depending on the substitution pattern, compounds 1 may have one or more centers of chirality, in which case they are present as pure enantiomers or diastereomers or as enantiomer or diastereomer mixtures. Both pure enantiomers or diastereomers and mixtures thereof are subject matter of the present invention.

[020] In the definitions of the symbols given in the Formulas herein, the collective terms used are generally representative for the following substituents: halogen: fluorine, chlorine, bromine and iodine;

C 1 -C 4 -Aquita: straight or branched chain saturated hydrocarbon groups having from 1 to 4 carbon atoms, such as methyl, etite, propyl. 1-trimethylethyl, butyl, 1-methylpropyl, 2-methyproppropite. 1,1-dimethylethyl. pentyl, 1-methylbutite, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl;

C 1 -C 4 haloalkyl: straight or branched chain alkyl groups having from 1 to 4 carbon atoms (as mentioned above), wherein some or all of the hydrogen atoms in these groups may be substituted with halogen atoms as mentioned above : in particular haiomethyl. such as chloromethyl, bromomethyl, dichloromethyl, chloromethyl, fluoromethyl. diftuormethyl, trifluoromethyl, chlorofluoromethyl, dichioroffuormethyl, chlorodifluormetite, and haloethyl such as 1-chloroethyl, 1-bromoethyl. 1-Fluorethyl, 2T-uoretyl, 2,2-difluoroethyl. 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1, 1,1-trifluoroprop-2-yl: C 3 -C 6 -cycloalkyl: monocyclic saturated hydrocarbon groups having from 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl or cictoexyl;

Preference is given to such compounds I and, as applicable, also to the compounds of all Sub-Formulas provided herein and, in particular, to the use and / or method of treatment as defined above of these compounds wherein substituents and the variables (such as R, R1, R2 and R3) independently of one another, or more preferably in combination, have the following meanings; According to one embodiment of the invention R is halogen, more preferably C1 or F, in particular Cl. According to the further embodiment, R is methyl. According to the further embodiment, R is hydrogen. According to the additional embodiment, both R and R2 are hydrogen. According to a further embodiment, R2 is C1 -C4 alkyl, more preferably methyl or ethyl. According to a further embodiment both R 1 and R 2 are C 1 -C 4 -alkyl, most preferably independently of each other methyl or ethyl and in particular both are methyl. According to the further embodiment, R1 and Rz together with the carbon atom joining them form a Cs-C6-cycloaryl, more preferably a cyclopropyl or cyclopentyl; in particular cyclopentyl. According to the further embodiment, R 3 is methyl or ethyl; in particular methyl. According to the further embodiment, R is hydrogen and R3 is methyl or ethyl; in particular methyl. According to the further embodiment, R is hydrogen and R3 is methyl or ethyl; in particular methyl.

Particular preference is given to the use and method of compound 1.1 having the following Formula;

Which according to the IUPAC nomenclature is (2E) -2-methoxy-2- [2 - [[(E) - [(2F} -2-methoxy-imino-1,4-dimethyl-pent * 3-enylidene] amino] oxymethyl> phenyl] -N-methyl acetamide.

Particular preference is given to the method for combating soybean rust as defined herein, wherein compound I is compound I 1, [025] Compounds i can be obtained as described in WO 00/0311023, [028] The term "material" is to be understood to denote all generating parts of the plant such as seeds, and plant vegetative material such as cuttings and tubers (e.g. potatoes) which may be used for This includes seeds, roots, fruits, tubers, bulbs, rhizomes, sprouts, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from the plant. These young plants can also be protected before transplantation by full or partial treatment by dipping or dumping.

Preferably, the treatment of plant propagation materials with compound I and compositions thereof, respectively, is used to control soybean rust in soybean.

[028] The term "soybean plants" needs to be understood to include soybean plants that have been modified through crossbreeding, mutagenesis or genetic engineering which includes, but is not limited to, agricultural biotechnology products on the market or under development ( see http://www.bio.org/speeches/pubs/ebaqri Products, asp, see GM's planting database in it). Genetically modified plants are plants from which genetic material has been so modified by recombinant DNA techniques that, under natural circumstances, it cannot readily be obtained by cross-species breeding. mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified phantom in order to improve certain plant properties. Such genetic modifications also include, but are not limited to, post-translational directed modification of protein (s), oligosaccharides. or polypeptides, for example by glycosylation or polymer additions such as prized, acetylated or farnesylated portions or PEG portions.

Plants that have been modified by mating, mutagenesis or genetic engineering, for example, that have become tolerant to applications of specific classes of herbicides such as auxinic herbicides such as dicamba or 2.4-D; "bleaching" herbicides such as hydroxyphenylpyruvate dioxigenase (HPPD) inhibitors or phytoene desaturase inhibitors (PDS); acetofactate synthase inhibitors (ALS) such as sulfonylurea inhibitors or imidazolinones: enolpyruvüshiquimate-3-phosphate synthase such as tEPSi phosphatase tEPSi) : glutamine synthase inhibitors, such as glufosinate inhibitors; protoporphyrinogen-IX oxidase; typical biosynthesis inhibitors such as acetyl CoA carboxytase (ACCase) inhibitors or oxinyl herbicides (i.e. bromoxynil or ioxinyl) as a result of conventional breeding methods In addition, plants have become resistant to multiple herbicide ciases through multiple genetic modifications, such as resistance to either glyphosate or glufosinate or to another glyphosate or urr herbicide, such as ALS inhibitors, HPPD inhibitors. auxinic herbicides or ACCase inhibitors. Herbicide resistance technologies are, for example, described in Pest Managem. Know. 61. 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005. 269; 61. 2005, 286: 64, 2008, 326; 64, 2008. 332; Weed Scí. 57, 2009, 108; Austral J. Agricuft. Res. 58, 2007, page 708; Science 316, 2007, page 1185 and references mentioned therein. Several cultivated plants have become herbicide tolerant by conventional breeding methods (mutagenesis). for example Imidazolinone-totalizing glearophyll. for example, imazamox. Genetic engineering methods have been used to make cultivated soybean, dicamba, glyphosate, imidazolmon and glufosinate plants or a combination of any of these elements, some of which are commercially available under the RoundupReady® (glyphosate tolerant, Monsanto) trademarks. , USA), Cultivance® (tolerant of imidazolinone BASF SE, Germany) and Ubertílink4 '(glufosinate tolerant, Bayer CropScience, Germany).

In addition, cereal plants are also encompassed which are, through the use of recombinant DNA techniques, capable of synthesizing one or more insecticidal proteins, especially those known in the bacterial genus Bacillus, particularly Bacillus thuringiensis. such as δ-endotoxins, for example Cry1Aibj. CrylA (o, CrylF, CrylF (a2). CryllA (b), CrylliA. CrytHB (b1) or Cry9c: plant insecticidal proteins (VIP), for example, VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from bacteria that colonize nematodes). eg Photorhabdus spp. or Xenorhabdus spp.; animal-produced toxins such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; fungal toxins such as streptomycetes toxins, lectmas such as pea or barley lectins; agglutinins: proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; rhinosome inactivation proteins (RIPs) such as ricin, RIPs corn, april, lufin, saporin or brydine, steroid metabolism enzymes such as 3-hydroxy steroid oxidase, ecdesteroid-IDP glycosyltransferase oxidases, cholesterol oxidases, ecdisone inhibitors or HMG-CoA reductase u; ion channel blockers such as sodium or calcium channel blockers; this juvenile hormone phase: diuretic receptors (helicoquinine receptors); stifbene synthase, benzoyl synthase, chitinases or gtucanases. In the context of the present invention, such insecticide proteins or toxins need to be expressly understood also as pre-toxins, hybrid proteins and truncated or otherwise modified proteins. Hybrid proteins are characterized by a novel combination of protein domains (see, for example, WO 02/015701). In addition, plants are also encompassed which, through the use of recombinant DNA techniques, are capable of synthesize one or more proteins to increase the resistance or tolerance of these plants to bacterial pathogens. viral or fungal. Examples of such proteins are so-called "pathogenesis-related proteins" (PR proteins, see, for example, EP-A 392 225), plant disease resistance genes or T4-lysozyme. Producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

In addition, plants that are, through the use of recombinant DNA techniques, capable of synthesizing one or more proteins to increase yield (eg, biomass production, grain yield, starch content, protein content), tolerance to drought, salinity or other growth limiting environmental factors, or tolerance to fungal pests and pathogens. [033] According to the further embodiment, compound I is additionally suitable for controlling in soybean plants the phytopathogenic fungi selected from Cercospora sojina and C. kikuchi, Coileotrichum gloeosporíoides, Corynespora cassicola ( leaf spot), Demaíophom (meiosis stage: Rosellinia) necatrix (stem or root rot), Diaporthe spp., eg D. phaseoforum (Stalking), Fusarium solani, Microsphaera diffusa (mildew), Peronospora manshurica (mildew), Phakopsora pachyrhizi and P. meihomiae (soybean rust), Phytophthora megasperma (synonym for P. soye), Rhizocionia solam (stem or root rot), Septoria gfycines (speckled spot) and Thielaviopsis spp. (black root rot).

[034] Compound 1 and its compositions, respectively, may be used to improve the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagating material and / or the location where the plant is grown or will be grown with an effective amount of the compounds I and the compositions thereof. respectively. Preferably, the invention relates to use for improving the health of the soybean plant.

[035} The term "plant health" is to be understood as denoting a condition of the plant and / or its products that is determined by various indicators alone or in combination with each other, such as yield (eg biomass). increased and / or increased content of valuable ingredients), plant vigor (eg improved plant growth and / or redone greener leaves ")), quality (eg content or composition of certain ingredients) and stress tolerance abiotic and / or biotic The indicators identified above for the health of a plant may be interdependent or may result from each other.

The compound is in the formula! may be present in different crystalline modifications from which biological activity may differ. They are similarly subject matter of the present invention.

[037] Compound I is employed as ta! or in the form of compositions by treating the fungi or plants and plant propagating materials, such as seeds, or soil, with a fungicidal effective amount of the at-vas substances. Application can be performed both before and after infection of plants and soybean propagating material. such as seeds, or soil, Plant propagation materials may be treated with compounds i as such or in a composition comprising at least one compound I prophylactically both before and during planting and transplantation. ] The invention also relates to agrochemical compositions comprising an auxiliary and a compound I according to the invention.

[040] An agrochemical composition comprises a fungicidal effective amount of a compound 1. The term "effective amount" denotes an amount of the composition or compounds 1 which is sufficient to control harmful fungi in crop plants or in the protection of materials and not results in substantial damage to the treated plants. Such amount may vary over a wide range and is dependent on various factors such as the fungal species to be controlled and the weather conditions.

Compound i can be converted into standard types of agrochemical compositions, for example emulsion solutions, dust suspensions, powders, pastes, granules, presses, capsules and mixtures thereof. Examples for composition types are suspensions (eg SC, OD, FSi. Emulsifiable concentrates (eg EC), emulsions (eg EW, EG ES, ME), capsules (eg CS. ZC). humidifiable pastes, pastes, powders or dusts (eg WP. SP. WS. DP, DS), pressed (eg BR, TB, DT), granules (eg WG SG. GR, FG, GG , MG), insecticidal articles (eg LN), as well as gel formulations for the treatment of plant oropagation materials such as seeds (eg GF), These and other types of compositions are defined in the Catalog of pesticide Formulation Types and International Coding System ”, Technique Monograph No. 2,6,6® Ed. Mar: 2008, CropLife International.

[042] The compositions are prepared in a known manner as described by Moüet and Grubemann, Formulation Technology, VCHI Wechheim, 2001. or Knowles. New devebpments in crop protection product formulation. Agrow Reports DS243, T&F Informa, London. 2005

Suitable auxiliaries are solvents, liquid packers, solid packers or fillers. surfactants. dispersants, emulsifiers, humidifiers. adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, food stimulants, compatibilizers. bactericides, antifreeze agents, defoaming agents, coloring agents. tackifiers and binders.

Suitable liquid solvents and carriers are water and organic solvents such as medium to high boiling mineral oil fractions, eg kerosene, diesel oil: animal and vegetable oils; aliphatic, cyclic and aromatic hydrocarbons, for example toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, for example ethanoyl, propanof, butanol, benzyl alcohol, cyclohexanol; giants; DIVISION; ketones, for example cyclohexanone: esters, for example lactates, carbonates, fatty acid esters, gamma butyrolactone; fatty acids: phosphonates; amines; amides, for example. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

[045] Suitable solid carriers or fillers are mineral earth, eg silicates, silica gels. talc, kaolin, limestone, lime. chalk. clays, dolomite. diatomaceous earth, bentonite. caustic sulfate, magnesium sulfate, magnesium oxide; polysaccharides. e.g. cellulose, starch; fertilizers, for example ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, eg cereal flour, tree bark flour, wood flour and nut shell flour and mixtures thereof, [046] Suitable surfactants are surface active compounds such as anionic surfactants, cationic, nonionic and amphoteric, block polymers, polyelectrolytes and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, humidifiers, penetration enhancers, protective colloid or adjuvant. Examples of surfactants are listed in McCutcheons, Vol.1: Emulsifiers & Detergent, McCutcheon's Directories, Glen Rock, USA, 2008 ( Ed, International or Ed. From North America).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha olefin sulfonates, lignin sulfonates, fatty acid and oil sulfonates, ethoxylated alkylphenol sulfonates, alkoxylated aryphenol sulfonates. condensed naphthalene sulfonates, dodecyl and tridecylbenzenes sulfonates, naphthalene and alkylnaphtatene sulfonates, sutphosucinates or sulfosucinamates. Examples of sulfates are fatty acid and oil sulfates, ethoxylated alkylphenols, alcohols, ethoxylated alcohols or fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are carboxylated alkyl and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar based surfactants, polymeric surfactants and mixtures thereof. Examples of alkoxyoxy compounds are compounds such as alcohols, alkoxyphenols, amines. beloved, ariphenols. fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide may be employed for alkoxyation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are glucamides. of fatty acid or fatty acid afcanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar based surfactants are sorbitans, ethoxylated sorbitans. saccharin and glucose or alkyloxyglucoside esters. Examples of polymeric surfactants are vinyl pyrrolidone homopotomers and co-isomers vinyl alcohols or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants, for example, quaternary ammonium compounds with one or two hydrophobic groups or primary chain amine salts. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are type A-B or A-ΒΆ block polymers comprising polyethylene oxide blocks and polypropylene oxide or type A-B-C blocks comprising alkanoyl, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkaline salts of polyacrylic acid or comb-like polyacid polymers. Examples polybases are polyvinyl amines or polyethylene amines.

Suitable adjuvants are compounds which have negligible or zero pesticidal activity by themselves, and which enhance the biological performance of compound I on the target. Examples are surfactants, mineral or vegetable oils and other auxiliaries. Additional examples are listed by Knowles. Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

Suitable thickeners are polysaccharides (e.g., xanthan gum, carboxymethylcellulose). inorganic clays (organically modified or unmodified), polycarboxylates and smcates.

Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoinones and benzisothiazolinones.

[053] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.

Suitable defoaming agents are silicones, long chain alcohols and fatty acid salts.

Suitable co -ants (eg in red, blue or green) are low water solubility pigments and water soluble inks. Examples are inorganic dyes (eg iron oxide, titanium oxide, iron hexacyanoferrate) and organic dyes (eg alizarin, azo- and phphalodanine dyes).

Suitable tackifiers or binders are polyvinylpyrrolidones, polyvinylacetates. polyvinyl alcohols, polyacrylates. biological or synthetic waxes and cellulose ethers.

Examples for composition types and preparations are: (i) 10 to 60% by weight water soluble concentrates (SL, LS) of a compound 1 and 5 to 15% by weight of wetting agent (e.g. alcohol} are dissolved in water and / or a 100% by weight water soluble solvent (eg alcohols), the trap substance dissolves upon dilution with water ii) Dispersible Concentrates (DC) 5 to 25% by weight of a compound I and 1 to 10 wt.% dispersant (e.g., polyMnpyrrolidone) are dissolved in 100% by weight organic solvent (e.g. cyclohexanone). Dilution with water provides a dispersion. iff) Emulsifiable concentrates (EC) 15 to 70% by weight of a compound I and 5 to 10% by weight of emulsifiers (eg calcium dodecylbenzenesuifonate and castor oil ethoxylate) are dissolved in water insoluble organic solvent (eg 100% wt. Dilution with water provides an emulsion. iv) Emulsions (EW, EO, ES) 5 to 40 wt.% of a compound 1 and 1 to 10 wt.% of emulsifiers (eg calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20 to 40 wt% of water-insoluble organic solvent (eg aromatic hydrocarbon). This mixture is introduced into 100 wt% water by means of an emulsifying machine and becomes a homogeneous emulsion. Dilution with water provides an emulsion. v) Suspensions (SC, OD, FS) In an agitated ball mill, 20 to 60 wt% of a compound I is sprayed with the addition of 2 to 10 wt% of dispersants and wetting agents (e.g. sodium and alcohol ethoxylate), 0.1 to 2 wt% tackifier (eg xanthan gum} and 100 wt% water to give a fine suspension of active substance. Dilution with water provides a stable suspension For the FS-type composition, up to 40 wt% fig (eg polyvinyl alcohol) is added vi) Water dispersible granules and water soluble granules (WG, SG) 50 to 80 wt% of a compound are finely milled with the addition of dispersants and wetting agents (eg sodium isosulfonate and alcohol ethoxy) at 100% by weight and prepared as water-dispersible or water-soluble granules by technical apparatus (e.g. extrusion, tor sprinkler, fluidized bed). Dilution with water provides a stable dispersion or solution of the active substance. vii) Water dispersible powders and water soluble powders (WP, SP, WS) 50 to 80% by weight of a compound! are milled in a rotor-stator mill with addition of 1 to 5 wt% dispersants (eg sodium isosulfonate), 1 to 3 wt% wetting agents (eg alcohol ethoxy) and a solid carrier (e.g. silica gel) 100% by weight. Dilution with water provides a stable dispersion or solution of the active substance. viii) Gel (GW, GF) in a stirred ball mill, from 5 to 25 wt% of a compound I are sprayed with the addition of 3 to 10 wt% dispersants (eg sodium isosulfonate), 1 to 5% by weight of tackifier (eg carboxymethylcellulose) and 100% by weight water to provide a fine suspension of the active substance. Dilution with water provides a stable suspension of the active substance. (ix) Microemulsion (ME) 5 to 20% by weight of a compound I is added to 5 to 30% by weight of organic solvent (eg fatty acid dimethylamide and cyclohexanone), 10 to 25% by weight of surfactant (eg ethoxy and arylphenol ethoxy alcohol) and 100% water. This mixture is stirred for 1 hour to spontaneously produce a thermodynamically stable microemulsion. (x) Microcapsules (CS) An oil phase comprising from 5 to 50% by weight of a compound (0.0 to 40% by weight of water-insoluble organic solvent (eg an aromatic hydrocarbon), 2 to 15% by weight). Acrylic monomers (for example methymethacrylate, methacrylic acid and a di- or tracrylate) are dispersed in an aqueous solution of a protective colloid (eg polyvinyl alcohol). Free radical polymerization results in the formation of poSi (meth) acrylate microcapsules. Alternatively, an oil phase comprising from 5 to 50% by weight of a compound! According to the invention, 0 to 40% by weight of water-insoluble organic solvent (for example, an aromatic hydrocarbon) and an isocyanate monomer (for example diphenylmetene-4,4'-diisodanate) is dispersed in an aqueous solution of a protective colloid (e.g. polyvinyl alcohol) The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. Monomers correspond to 1 to 10 wt%, wt% refers to the total composition CS, xi) Sprinkles (DP, DS) From 1 to 10 wt% of a compound I are finely ground and intimately mixed with a 100% by weight solid carrier (eg split fine amine kaolin), xii) Granules (GR, FG) From 0.5 to 30% by weight of a compound I is finely ground and associated with a solid carrier ( e.g. silicate) 100% by weight. Granulation is achieved by extrusion, spray drying or fluidized bed. Ultra Low Volume (UL) Liquids From 1 to 50% by weight of a compound I are dissolved in 100% by weight organic solvent (e.g. aromatic hydrocarbon).

The types of compositions of i) to xiii) may optionally comprise additional auxiliaries such as from 0.1 to 1 wt% of bacteria from 5-15 wt% of antifouling agents, 0.1 to 1 wt%. weight of antifoaming agents, and 0.1 to 1% by weight of colorants. The agrochemical compositions generally comprise from 0.01 to 95%, preferably from 0.1 to 90%, and in particular from 0.5 to 75%. by weight of the active substance. The active substances are employed in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

For the purposes of foliar treatment, agrochemical compositions are preferably types of chemical formulation compositions such as suspensions (eg SC, OD, FS), inflatable concentrates (eg EG) and emulsions (eg EW). , EO, ES, ME); and comprise from 100 to 500 g of compounds I per liter, even more preferably from 200 to 400 g of compounds I per liter. For the purposes of treating plant propagating material, particularly seed, solutions seed treatment (LS) Suspoemulsions (SE), fluid concentrates (FS), dry treatment powders (DS), water dispersible mud treatment powders (WS), water soluble powders (SSj, emulsions (ES)) Emulsifiable Concentrates (EC) and Gels (GF) are commonly employed The compositions in question provide, after a dilution of two to ten stages, active substance concentrations of 0.01 to 60% by weight, preferably from 0.1 to 40% in ready-to-use preparations Application may be performed before or during sowing Methods for applying compound I and compositions thereof, respectively, to plant propagation material, especially seeds, include methods of covering coating, pelletizing, dusting and dipping as well as furrow application methods. Preferably, compound f or compositions thereof, respectively, are applied to plant propagation material by a method such that germination is not induced, for example, by covering, pelleting, coating and seed sprinkling, [062] Em treatment of plant propagation materials such as seeds, for example when spraying, coating or soaking seeds, amounts of the active substance from 0.01 to 10 kg, preferably from 1 to '000 g, more preferably from 1 to 100 g. most preferably from 5 to 100 g per 100 kilograms of plant propagating material (preferably seeds) are generally required.

Accordingly, the present invention also relates to seeds coated with compound I, for example in an amount from 0.1 g to 10 kg per 100 kg of seeds. Accordingly, the present invention also relates to seeds comprising compound I, for example, in an amount of from 0 01 g to 10 kg per 100 kg of seeds. Preferably these seeds are soybean seeds.

[064] When used to protect materials or stored materials, the amount of active substance applied depends on the type of application area and the desired effect. The amounts normally applied for material protection are 0.001 g to 2 kg. preferably from 0.005 g to 1 kg of active substance per cubic meter of treated material.

[065] Various types of oils, humectants, adjuvants, fertilizers or micronutrients may be added to the active substances or compositions comprising them as premix or. appropriate, not until immediately prior to use [tank mix]. Such agents may be aggregated with the compositions according to the invention in a weight ratio of 1: 160 to 100: 1, preferably 1:10 to 10: 1. I. Synthesis Examples Compound 1.1 was obtained according to methods described in WO 00/0311023. With modifications appropriate to the starting materials, these procedures can be used to obtain additional compounds I. The resulting compounds, along with physical data, are listed in Table I below, Table I. Physical Step Formula Compounds (P Fusion Point). CI: 1 H NMR (CdCl3) (Δ): HPLC / MS Retention Time (1 H, Nl) 1. Comparative Examples for Fungicide A Activity, GREENHOUSE TESTS

Sprinkling solutions were prepared in several steps: The stock solution was prepared: a mixture of acetone and / or dimethylsulfoxide and the wetting / emulsifying agent Wettol, which is based on ethoxylated alkylphenols, in a solvent ratio (volume). 99 to 1 emulsifier was added to 25 mg of the compound to provide a total of 5 ml.

The water was then added to the total volume of 100 ml. This stock solution was diluted with the mixture of solvent, emulsifier and water described at the concentration provided.

Example Of Smooth 1: The Curative Control Of Soybean Rust In Soya Beans Caused By Fhakopsqra Pachyrhizi {070] The '' eyes of soybean seedlings grown in pots were inoculated with Phakopsora pachyrhizi spores, To ensure the success of artificial inoculation, the plants were transferred to a humid chamber with a relative humidity of approximately 95% and from 20 to 24 ° C for 24 h.The next day the plants were grown for 3 days in a 23 to 27: C greenhouse chamber and the 60% to 80% relative humidity. Then the plants were sprayed to runoff with an aqueous suspension containing the active ingredient concentration or mixture as described below. The plants were allowed to air dry. The assay was grown for 14 days in a greenhouse chamber at 23 to -27 ° C and at a relative humidity between 60 and 80%, The extent of leaf fungal attack was evaluated as% of the diseased leaf area.Fungicidal activity was determined with Abbot's Formula. The results are given in the following table.

Claims (11)

1. USE OF COMPOUNDS OF FORMULA I characterized by the fact that R is hydrogen, halogen or methyl; R1, R2 are independently selected from hydrogen, C1 -C4 alkyl and C1 -C4 haloalkyl; or R1 and R2 together with the bonding carbon atom form Ca-C6 -cycloalkyl; R3 is C1 -C4 -alkyl; to combat soybean rust. Use according to claim 1, characterized in that the use is of the compounds of Formula I and wherein R is hydrogen. Use according to any one of claims 1 and 2, characterized in that the use is of the compounds of Formula 1 and wherein both R 1 and R 2 are C 1 -C 4 -alkyl. Use according to any one of claims 1 to 3, characterized in that the use is of the compounds of Formula I and wherein R 3 is methyl. Use according to claim 4, characterized in that the use is of the compound of formula 1.1. Use according to any one of claims 1 to 5, characterized in that the use is for combating Phakopsora pachyrhizi and / or P. meihomiae (soybean rust) in soybean plants. Use according to any one of claims 1 to 6, wherein the use is for combating Phakopsora pachyrhizi and / or P, meibomiae (soybean rust) and at least one additional soybean pathogen selected from Cercospora sojina. and C. kikuchi, Coileotrichum gioeosporioides. Corynespora cassia (leaf spot), Dematophora mernsporic stage: Roseliinia) necatrix (stem or root rot), Diaporthe spp. for example. D. phaseolorum (Estiolamento), Fusa in a sole Microsphaera diffusa (o'diO), Peronospora manshurica (downy mildew), Phytophthora megasperma (synonym for P, soybean). Rhizoctonia solam (stem or stem rot). If you put giycines (speckled spot) and Thielaviopsis spp. (black root rot). 8. METHOD FOR COMBATING RUST. characterized in that it comprises: treating the soybean plants or the propagating material of the soybean plant to be protected against attack by Phakopsora pachyrhizi and / or P. meihomiae with an effective amount of at least one compound of Formula 1 as defined in any one of claims 1 to 5, or the composition comprising such compound of formula I as defined in any one of claims 1 to 5. USE OF COMPOUND FORMULA I. As defined in any one of claims 1 to 5, characterized in that it is for improving the health of the soybean plant; Seed coated with the compound of formula I as defined in any one of claims 1 to 5, characterized in that it is an amount of 0.01 g to 10 kg per 100 kg of seeds. characterized by the fact that R is hydrogen, halogen or meda. R \ R "are independently selected from hydrogen, C 1 -C 1 alkyl and C 1 -C 4 haloalkyl; or R 1 and R 2 together with the carbon atom that binds them form C-C 2 -C 6 -C 6 -C 6 -C 6 -C 6 -C 6 -C 6 -C 6 -C 6 -C 6 -C 6 R 3 is C 1 -C 4 -alkyl, except for (2E) -2-methoxyimino-2- [2 - [[(E) - [(2E) -2-methoxy-1,4-dimethyl-pentoxy] 3-en-ylidene] amino] oxomet (1] -phenyl] -N-methoxyacetamide. AGROCHEMICAL COMPOSITIONS, characterized in that said compositions comprise an auxiliary and at least one compound of Formula I as defined in claim 11.