WO2019043183A1 - Procédé de lutte contre les nuisibles du riz dans le riz - Google Patents

Procédé de lutte contre les nuisibles du riz dans le riz Download PDF

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Publication number
WO2019043183A1
WO2019043183A1 PCT/EP2018/073516 EP2018073516W WO2019043183A1 WO 2019043183 A1 WO2019043183 A1 WO 2019043183A1 EP 2018073516 W EP2018073516 W EP 2018073516W WO 2019043183 A1 WO2019043183 A1 WO 2019043183A1
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WO
WIPO (PCT)
Prior art keywords
rice
compound
methyl
formula
borer
Prior art date
Application number
PCT/EP2018/073516
Other languages
English (en)
Inventor
Joachim Dickhaut
Huazhang Huang
Anil Menon
Original Assignee
Basf Se
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 Basf Se filed Critical Basf Se
Priority to JP2020511993A priority Critical patent/JP7233415B2/ja
Priority to KR1020207005880A priority patent/KR102659381B1/ko
Priority to CN201880055160.2A priority patent/CN111031798A/zh
Publication of WO2019043183A1 publication Critical patent/WO2019043183A1/fr
Priority to PH12020500312A priority patent/PH12020500312A1/en

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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • Rice (Oryza species, especially Oryza sativa) is an important basic food in the world. It is a staple food in Asia and is an important part of many cultures. Rice is therefore an important crop and is cultivated in large areas, especially in Asia.
  • the invention relates to a seedling box application method of controlling rice pest invertebrates in rice, which method comprises applying to said rice pest invertebrates com- pound of formula (I)
  • the invention in another aspect, relates to a method of controlling rice pest invertebrates in rice, which method comprises applying to said rice pest invertebrates compound of formula (I) by seedling box application.
  • WO 2014/167084 and PCT/EP2018/057578 describe certain substituted pyrimidinium com- pounds with heterocyclic substituents for combating invertebrate pests.
  • the compound of formula (I) is present in two enantiomeric forms l-R-1 and l-S-1 as shown below
  • compositions comprising compound of formula (I), for use in controlling rice pests, especially rice pest invertebrates, in rice, by seedling box application;
  • compositions comprising an amount of compound of formula (I) or an enantio- mer, diasteromer or salt thereof as defined above, for controlling rice pests, especially rice pest invertebrates, in rice, by seedling box application;
  • a method for combating rice pest invertebrates, infestation, or infection by rice pest invertebrates comprises applying said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of compound of formula (I) as defined above or a composition thereof, by seedling box application;
  • a method for controlling rice pest invertebrates, infestation, or infection by invertebrate pests comprises applying said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of of formula (I) as defined above or a composition comprising compound of formula (I), by seedling box application;
  • - a method for protecting rice, rice plants, rice plant propagation material and/or growing rice plants from attack or infestation by rice pest invertebrates comprising contacting or treating the rice, rice plants, rice plant propagation material and growing rice plants, or soil, material, surface, space, area or water in which the rice, rice plants, rice plant propagation material is stored or the rice plant is growing, with a pesticidally effective amount of compound of formula (I) as defined above or a composition comprising compound of formula (I), by seedling box application; - a method for increasing the health of rice plants, especially in paddy rice fields, comprising the treatment with compound of formula (I), by seedling box application;
  • the present invention relates to and includes the following embodiments:
  • - seeding box comprising a compound of formula (I), for use in controlling rice pests, especially rice pest invertebrates, in rice;
  • - nursery box comprising a compound of formula (I), for use in controlling rice pests, especially rice pest invertebrates, in rice;
  • - seeding box application method comprising agricultural compositions comprising an amount of a compound of formula (I) or an enantiomer, diasteromer or salt thereof as defined above, for use in controlling rice pests, especially rice pest invertebrates, in rice;
  • a seeding box application method for combating rice pest invertebrates, infestation, or infection by rice pest invertebrates comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of a compound of formula (I) as defined above, or a composition thereof;
  • a seeding box application method for controlling rice pest invertebrates, infestation, or infec- tion by invertebrate pests which method comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of a compound of formula (I) as defined above, or a composition comprising compound of formula (I);
  • a seeding box application method for preventing or protecting against rice pest invertebrates comprising contacting the rice pest invertebrates, or their food supply, habitat or breeding grounds with a compound of the formula (I) as defined above or a composition comprising a compound of formula (I) as defined above, or a composition comprising a compound of formula
  • a seeding box application method for protecting rice, rice plants, rice plant propagation material and/or growing rice plants from attack or infestation by rice pest invertebrates comprising contacting or treating the rice, rice plants, rice plant propagation material and growing rice plants, or soil, material, surface, space, area or water in which the rice, rice plants, rice plant propagation material is stored or the rice plant is growing, with a pesticidally effective amount of a compound of formula (I) as defined above, or a composition comprising compound of formula
  • the present invention relates to nursery boxes comprising a growth substrate for rice, rice seeds and an aqueous formulation of a compound of formula (I) for treating said rice seeds to protect rice plants against insects for a prolonged period of time.
  • the invention further relates to a new process for the treatment of rice crops using an insecticidal product containing a compound of formula (I), and more especially a new process for the treatment of rice crops against parasites called stem borers (Chilo spp.) and plant hoppers (Nilparvata lugens), as well as other parasites such as weevils (Lissorhoptrus oryzophilus).
  • Other parasites are advantageously eliminated by the process according to the invention, especially the nematode Aphelencoides bes- seyi, and the mining fly Hydrellia philiippina.
  • the latter relates to a process for treating rice plants or rice propagation material against insects with a view to obtaining a sustained and ef- fective protection of the plant after the sowing period, characterised in that there is applied to the said plants or, preferably, to their propagation material, an effective amount of compound of formula I.
  • the propagation material used is the rice seed or, in other words, rice grains.
  • the insecticidal material used is that which will be defined below.
  • the present invention relates to and includes the following embodiments:
  • - seeding box comprising agricultural compositions comprising an amount of a compound of formula (I) or an enantiomer, diasteromer, or salt thereof as defined above;
  • the - seeding box comprising the compound of formula (I), wherein the amount of the compound of formula (I) impregnated into the rice seeds is between about 3 and 200 g/q, preferably between about 3 and 100 g/q, more preferably between about 6 and 25 g/q.
  • All the compounds of the present invention including their stereoisomers, their tautomers, their salts or their N-oxides as well as compositions thereof are particularly useful for controlling invertebrate rice pests, in particular for controlling arthropods and nematodes and especially in- sects. Therefore, the invention relates to the use of a compound as disclosed in the present invention, for combating or controlling invertebrate rice pests, in particular invertebrate pests of the group of insects, arachnids or nematodes by seedling box application.
  • the term "Seedling box applications” refers to manual or mechanical incorporation of insecticide formulations (for eg. granules, liquid) in nursery boxes or seedling boxes containing rice seedlings before being transplanted into the main field.
  • compound(s) according to the invention or “compound(s) of formula (I)” or “com- pound I or (I)” as used in the present invention refers to and comprises the compound(s) as defined herein and/or stereoisomer(s), salt(s), tautomer(s) or N-oxide(s) thereof.
  • compound ⁇ ) of the present invention is to be understood as equivalent to the term “compound(s) according to the invention”, therefore also comprising stereoisomer(s), salt(s), tautomer(s) or N- oxide(s) of compounds of formula (I).
  • composition(s) according to the invention or “composition(s) of the present invention” encompasses composition(s) comprising compound of formula (I) according to the invention as defined above, therefore also including a stereoisomer, an agriculturally or veterinary ac- ceptable salt, tautomer or an N-oxide of the compounds of formula (I).
  • the compounds of formula (I) are present in mesomeric forms. These forms may be expressed in different isoelectronic formulae, each having the formal positive and negative charges on different atoms (as shown below).
  • the present invention extends to all representa- tive isoele
  • the compounds of formula (I) are present as mixtures of enantiomers or diastereomers.
  • the invention provides both the single pure enantiomers or pure diastereomers of the compounds of formula (I), and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula (I) or its mixtures.
  • stereoisomer(s) encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
  • the present invention relates to every possible stereoisomer of the compounds of formula (I), i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.
  • Preferred embodiments of specific enantiomers are described in more detail below, as compounds of formula (l-R-1 ) and (l-S-1 ).
  • Salts of the compounds of the formula (I) are preferably agriculturally and/or veterinary acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula (I) has a basic functionality or by reacting an acidic compound of formula (I) with a suitable base.
  • Suitable agriculturally or veterinary useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxy- alkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetrae- thylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl-am- monium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammo- nium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate, and butyrate. They can be formed by reacting the compounds of formula I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, or nitric acid.
  • N-oxide includes any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.
  • the compounds of formula (I) can be prepared as described in WO2014/167084 and
  • Agronomically acceptable salts of the compounds I can be formed in a customary manner, e.g. by reaction with an acid of the anion in question.
  • the invention relates to a seedling box application method of controlling rice pest invertebrates in rice as described herein, wherein the compound of formula (I) is the compound l-R-1 , salt, or N-oxide thereof.
  • the invention relates to a method of controlling rice pest invertebrates in rice by seedling box application as described herein, wherein the compound of formula (I) is the compound l-R-1 , salt, or N-oxide thereof.
  • the compound of formula (I) is the compound l-S-1 .
  • rice pest invertebrates are animal pests, which occur in rice.
  • the rice pest invertebrates include insects, acarids, and nematodes, preferably insects.
  • Rice pest invertebrates, which are well-known in rice, include but are not limited to the following spe- cies:
  • rice blackbug - Scotinophora vermidulate S. vermidulate, S. lurida, S. latiuscula
  • Thysanoptera
  • Gryllus bimaculatus Teleogryllus occipitalis
  • Hymenoptera ants - Solenopsis geminata
  • rice is affected by a range of bugs including Leptocorisa chinensis, Lagynotomus elongates, Nerzara viridula, Eysacoris parvus, Leptocorisa oratorius, Oebalus pugnax, Cletus trigonus, as well as a variety of mites, caterpillars, beetles, rootworms and maggots.
  • bugs including Leptocorisa chinensis, Lagynotomus elongates, Nerzara viridula, Eysacoris parvus, Leptocorisa oratorius, Oebalus pugnax, Cletus trigonus, as well as a variety of mites, caterpillars, beetles, rootworms and maggots.
  • the rice pest invertebrate is a biting/chewing insect.
  • the rice pest invertebrate is a piercing/sucking insect.
  • the rice pest invertebrate is a rasping insect.
  • the rice pest invertebrate is a siphoning insect.
  • the rice pest invertebrate is a sponging insect.
  • the rice pest invertebreate is from the order Hemiptera or Lepidoptera.
  • the rice pest invertebrate is from the order Hemiptera.
  • the rice pest invertebrate is a hopper, preferably selected from brown planthopper (Nilaparvata lugens), small brown planthopper (Laodelphax striatellus), white-backed planthop- per (Sogatella furcifera), green leafhopper (Nephotettix virescens).
  • the rice pest invertebrate is selected from brown planthopper (Nilaparvata lugens) and green leafhopper (Nephotettix virescens), preferably brown planthopper (Nilaparvata lugens).
  • the rice pest invertebrate is the brown planthopper (Nilaparvata lugens).
  • the rice pest invertebrate is the green leafhopper (Nephotettix virescens).
  • the rice pest invertebrate is a stink bug, preferably selected from rice stink bugs (Nezara viridula, Pygomenida varipennis, Eysarcoris, Tibraca limbatriventris, Eysar- coris ventralis) or small stink bug (Oebalus poecilus, O. pugnax).
  • the rice pest invertebrate is from the order Lepidoptera.
  • the rice pest invertebrate is the rice leafroller / leaf folder (Cnaphalocrocis medinalis, Marasmia patnalis, M. exigua).
  • the rice pest invertebrate is from the order Coleoptera.
  • the rice pest invertebrate is water weevil (Lissorhopterus oryzophilus).
  • the rice pest invertebrate is rice weevil (Oryzophagus oryzae).
  • the rice pest invertebrate is from the family of termites (order Isoptera). In a preferred embodiment, the rice pest invertebrate is Lissorhoptrus oryzophilus.
  • the present invention also relates to methods according to the invention, applying a mixture of at least one compound of the present invention with at least one mixing partner as defined herein after.
  • Preferred weight ratios for such binary mixtures are from 5000:1 to 1 :5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1 :100, particularly preferably from 10:1 to 1 :10.
  • components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.
  • Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers, and the like.
  • Preferred mixing partners are insecticides, nematicides and fungicides.
  • M.1 Acetylcholine esterase (AChE) inhibitors M.1 A carbamates, e.g.
  • aldicarb alanycarb, ben- diocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triaza- mate; or M.1 B organophosphates, e.g.
  • GABA-gated chloride channel antagonists M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;
  • M.3 Sodium channel modulators from the class of M.3A pyrethroids e.g. acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin (in particular kappa-bifenthrin), bioallethrin, bio- allethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esf
  • M.4 Nicotinic acetylcholine receptor agonists nAChR: M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M.4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine,
  • M.4A.2 (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1 -[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroim- idazo[1 ,2-a]pyridine; or M.4B nicotine; M.4C sulfoxaflor; M.4D flupyradifurone; M.4E triflume- zopyrim;
  • Nicotinic acetylcholine receptor allosteric activators e.g. spinosad or spineto- ram;
  • M.6 Chloride channel activators from the class of avermectins and milbemycins, e.g.
  • abamectin emamectin benzoate, ivermectin, lepimectin, or milbemectin;
  • M.7 Juvenile hormone mimics such as M.7A juvenile hormone analogues hydroprene, kino- prene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;
  • M.8 miscellaneous non-specific (multi-site) inhibitors e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M.8B chloropicrin, M.8C sulfuryl fluoride, M.8D borax, or M.8E tartar emetic;
  • M.9 Chordotonal organ TRPV channel modulators e.g. M.9B pymetrozine; pyrifluquinazon; M.10 Mite growth inhibitors, e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M.10B etoxazole;
  • M.12 Inhibitors of mitochondrial ATP synthase e.g. M.12A diafenthiuron, or M.12B organotin miticides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetra- difon;
  • chlorfenapyr DNOC, or sulfluramid
  • Nicotinic acetylcholine receptor (nAChR) channel blockers e.g. nereistoxin analogues bensultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;
  • M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
  • benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
  • M.16 Inhibitors of the chitin biosynthesis type 1 e.g. buprofezin;
  • Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufeno- zide, halofenozide, fufenozide, or chromafenozide;
  • Octopamin receptor agonists e.g. amitraz
  • M.20 Mitochondrial complex III electron transport inhibitors e.g. M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate;
  • M.21 Mitochondrial complex I electron transport inhibitors e.g. M.21A METI acaricides and in- secticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfen- pyrad, or M.21 B rotenone;
  • M.22 Voltage-dependent sodium channel blockers e.g. M.22A indoxacarb, M.22B metaflumi- zone, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1 -[3-(trifluoromethyl)phenyl]ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methylphenyl)-2-[(4- chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazi
  • M.23 Inhibitors of the of acetyl CoA carboxylase such as Tetronic and Tetramic acid derivatives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion
  • M.24 Mitochondrial complex IV electron transport inhibitors e.g. M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
  • Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;
  • M.28 Ryanodine receptor-modulators from the class of diamides e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N1 - ⁇ 2-methyl-4-[1 ,2,2,2 -tetra- fluoro-1 -(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1 -methyl-2-methylsulfonylethyl)phthalamid, M.28.2: (S)-3-Chloro-N1 - ⁇ 2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1 -methyl-2- methylsulfonylethyl)phthalamid, M.28.3: cyclaniliprole, or M.28.4: methyl-2-[3,5-dibromo-2
  • M.29 Chordotonal organ Modulators - undefined target site, e.g. flonicamid;
  • M.UN. insecticidal active compounds of unknown or uncertain mode of action e.g. afidopyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chino- methionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, tioxazafen, M.UN.3: 1 1 -(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]-tetradec- 1 1 -en-10-one,
  • M.UN.5 1 -[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H- 1 ,2,4-triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582);
  • M.UN.6 flupyrimin
  • M.UN.8 fluazaindolizine
  • M.UN.9.a) 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol- 3-yl]-2-methyl-N-(1 -oxothietan-3-yl)benzamide
  • M.UN.10 5-[3-[2,6- dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole;
  • M.UN.1 1 .b 3-(benzoylmethylamino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluorome- thyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide; M.UN.1 1.c) 3-(benzoylmethylamino)- 2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-b zamide; M.UN.1 1 .d) N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-(trifluorome- thyl)phenyl]amino]carbonyl]phenyl]-N-methyl
  • M.UN.12.a 2-(1 ,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M.UN.12.b) 2-[6-[2-(5- Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pynmidine; M.UN.12.C) 2-[6-[2-(3-Pyridinyl)-5-thia- zolyl]-2-pyridinyl]-pyrimidine; M.UN.12.d) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2- carboxamide; M.UN.12.e) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; M.UN.12.e) N-Methylsulf
  • M.UN.14a 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,67-hexahydro-5-methoxy-7-methyl-8-ni imidazo[1 ,2-a]pyridine; or M. UN.14b) 1 -[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol; M. UN.16a) 1 -isopropyl-N,5-dimethyl-N-pyndazin-4-yl-pyrazole-4-carboxamide; or M.
  • M.UN.16d 1 -[1 -(1 -cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carbox- amide
  • M.UN.16e N-ethyl-1 -(2-fluoro-1 -methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
  • M.UN.16f 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-car- boxamide
  • M.UN.16g 1 -[1 -(1 -cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
  • M.UN.16h N-methyl-1 -(2-fluoro-1 -
  • M. UN.17a N-(1 -methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide
  • M. UN.17b N-cyclo- propyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide
  • M.UN.17h N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide
  • M.UN.17i 2-(3- pyridinyl )-N-(2-pyrimidinylmethyl )-2H-indazole-5-carboxamide
  • M.UN.17j N-[(5-methyl-2-pyra- zinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide
  • M. UN.18a N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfanyl)pro- panamide; M. UN.18b) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfi- nyl)propanamide; M.
  • M.UN.21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1 -methyl-3-(1 ,1 ,2,2,2-pentaflu- oroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide;
  • M. UN.22a 2-(3-ethylsulfonyl-2-pyridyl)- 3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5-(trifluorome- thyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine;
  • M.UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(tri- fluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide;
  • M.UN.24a N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1 ,1 ,2,2,2-pentafluoro- ethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide or M.UN.24b) N-[4-chloro-3-[(1 -cyanocyclopro- pyl)carbamoyl]phenyl]-2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-car- boxamide; M.UN.25 acynonapyr; M.UN.26 benzpyrimoxan; M.UN.27 2-chloro-N-(1 -cyanocyclo- propyl)-5-[1 -[2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(tri
  • M.4 cycloxaprid is known from WO2010/069266 and WO201 1/069456.
  • M.4A.1 is known from CN 103814937; CN 105367557, CN 105481839.
  • M.4A.2, guadipyr, is known from WO 2013/003977, and M.4A.3 (approved as paichongding in China) is known from WO
  • M.22B.1 is described in CN10171577 and M.22B.2 in CN102126994.
  • Spiropidion M.23.1 is known from WO 2014/191271 .
  • M.28.1 and M.28.2 are known from WO2007/101540.
  • M.28.3 is described in WO2005/077934.
  • M.28.4 is described in WO2007/043677.
  • M.28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, WO2013/024009 and WO
  • M.28.5i is described in WO201 1/085575, M.28.5j) in WO2008/134969, M.28.5k) in US201 1/046186 and M.28.5I) in WO2012/034403.
  • M.28.6 can be found in WO2012/034472.
  • M.UN.3 is known from WO2006/089633 and M.UN.4 from WO2008/06791 1 .
  • M.UN.5 is described in WO2006/043635, and biological control agents on the basis of bacillus firmus are described in WO2009/124707. Flupyrimin is described in WO2012/029672.
  • M.UN.8 is known from WO2013/055584.
  • M.UN.9.a is described in WO2013/050317.
  • M.UN.9.b is described in WO2014/126208.
  • M. UN.10 is known from WO2010/060379. Broflanilide and M.UN.H .b) to M.UN.H .h) are described in WO2010/018714, and M.UN.1 1 i) to M.UN.H .p) in WO
  • M.UN.12.a) to M.UN.12.c) are known from WO2010/006713
  • M.UN.12.d) and M.UN.12.e) are known from WO2012/000896, and M.UN.12.f) to M.UN.12.m) from WO
  • M. UN.14a) and M. UN.14b) are known from WO2007/101369.
  • M.UN.16.a) to M.UN.16h) are described in WO2010/034737, WO2012/084670, and WO2012/143317, resp., and M.UN.16i) and M.UN.16j) are described in WO2015/055497.
  • M. UN.17a) to M.UN.17.j) are described in WO2015/038503.
  • M. UN.18a) to M.UN.18d) are described in US2014/0213448.
  • M.UN.19 is described in WO2014/036056.
  • M.UN.20 is known from WO2014/090918.
  • M.UN.21 is known from EP2910126.
  • M.UN.22a and M.UN.22b are known from WO2015/059039 and WO2015/190316.
  • M.UN.23a and M.UN.23b are known from WO2013/050302.
  • M.UN.24a and M.UN.24b are known from WO2012/126766.
  • Acynonapyr M.UN.25 is known from WO
  • Benzpyrimoxan M.UN.26 is known from WO2016/104516.
  • M.UN.27 is known from WO2016174049.
  • Inhibitors of complex III at Qo site azoxystrobin (A.1.1 ), coumethoxystrobin (A.1 .2), coumoxystrobin (A.1.3), dimoxystrobin (A.1 .4), enestroburin (A.1 .5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1.9), mande- strobin (A.1.10), metominostrobin (A.1 .1 1 ), orysastrobin (A.1 .12), picoxystrobin (A.1 .13), pyra- clostrobin (A.1 .14), pyrametostrobin (A.1 .15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2 (2-(3-(2,6-dichlorophen
  • inhibitors of complex III at Qi site cyazofamid (A.2.1 ), amisulbrom (A.2.2), [(6S,7R,8R) 8 benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7- yl] 2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4);
  • inhibitors of complex II benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), bos- calid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapy- roxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyrazi- flumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21 ), 3 (difluorome- thyl)-1 -methyl-
  • respiration inhibitors diflumetorim (A.4.1 ); nitrophenyl derivates: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); silthiofam (A.4.12);
  • Delta14-reductase inhibitors aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spirox- amine (B.2.8);
  • Inhibitors of 3-keto reductase fenhexamid (B.3.1 );
  • Sterol biosynthesis inhibitors chlorphenomizole (B.4.1 );
  • benalaxyl (C.1.1 ), benalaxyl-M (C.1 .2), kiral- axyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1 .5), ofurace (C.1 .6), oxadixyl (C.1 .7);
  • nucleic acid synthesis inhibitors hymexazole (C.2.1 ), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4 amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4 amine (C.2.7), 5-fluoro-2 (4 chlo- rophenylmethoxy)pyrimidin-4 amine (C.2.8);
  • tubulin inhibitors benomyl (D.1.1 ), carbendazim (D.1 .2), fuberidazole (D1.3), thiabendazole (D.1 .4), thiophanate-methyl (D.1.5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyri- dazine (D.1 .6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (D.1 .7), N ethyl-2- [(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8 methyl-6 quino- lyl)oxy]-2-methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinol-yl)oxy]
  • diethofencarb (D.2.1 ), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);
  • methionine synthesis inhibitors cyprodinil (E.1.1 ), mepanipyrim (E.1 .2), pyrimethanil (E.1.3);
  • blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);
  • MAP / histidine kinase inhibitors fluoroimid (F.1 .1 ), iprodione (F.1 .2), procymidone (F.1 .3), vinclozolin (F.1.4), fludioxonil (F.1 .5);
  • quinoxyfen F.2.1 ;
  • Phospholipid biosynthesis inhibitors edifenphos (G.1.1 ), iprobenfos (G.1 .2), pyrazophos (G.1.3), isoprothiolane (G.1 .4);
  • lipid peroxidation dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);
  • dimethomorph G.3.1
  • flumorph G.3.2
  • mandipropamid G.3.3
  • pyrimorph G.3.4
  • benthiavalicarb G.3.5
  • iprovalicarb G.3.6
  • valifenalate G.3.7
  • propamocarb G.4.1
  • - inhibitors of oxysterol binding protein oxathiapiprolin (G.5.1 )
  • 2- ⁇ 3-[2-(1 - ⁇ [3,5-bis(difluoro- methyl-1 H-pyrazol-1 -yl]acetyl ⁇ piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2 oxazol-5-yl ⁇ phenyl methanesulfonate G.5.2
  • 2- ⁇ 3-[2-(1 - ⁇ [3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl ⁇ piperidin-4- yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5 yl ⁇ -3-chlorophenyl methanesulfonate G.4.1
  • oxathiapiprolin G.5.1
  • thio- and dithiocarbamates ferbam (H.2.1 ), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
  • organochlorine compounds anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), cap- tan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1 );
  • guanidines and others guanidine (H.4.1 ), dodine (H.4.2), dodine free base (H.4.3), guaza- tine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3- c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10);
  • inhibitors of glucan synthesis validamycin (1.1 .1 ), polyoxin B (1.1 .2); melanin synthesis inhibitors: pyroquilon (1.2.1 ), tricyclazole (1.2.2), carpropamid (1.2.3), di- cyclomet (I.2.4), fenoxanil (I.2.5);
  • acibenzolar-S-methyl J.1.1
  • probenazole J.1.2
  • isotianil J.1.3
  • tiadinil J.1.4
  • prohexa- dione-calcium J.1.5
  • phosphonates fosetyl (J.1 .6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.1 1 ), potassium phosphonate (J.1 .12), potassium or sodium bicarbonate (J.1.9), 4 cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1 .10);
  • dipymetitrone isoflucypram
  • fluindapyr inpyrfluxam
  • pyrifenamine pyrifenamine
  • fungicides described by lUPAC nomenclature, their preparation and their pesticidal activ- ity is also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358; WO 02/225
  • WO 13/092224, WO 1 1/135833 CN 1907024, CN 1456054, CN 103387541 , CN 1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/1 16251 , WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/16551 1 , WO 1 1/081 174, WO 13/47441 ).
  • the compounds of the present invention are mixed with one or more fungicides, the mixtures are also suitable for combating or controlling plant diseases, as caused by phytophathogenic fungi.
  • phytophathogenic fungi in rice are examples of phytophathogenic fungi in rice.
  • Bipolaris e.g. Bipolaris oryzae
  • Drechslera species on rice Cercospora oryzae, Cochliobolus miyabeanus, Curvularia lunata, Sarocladium oryzae, S atten- uatum, Entyloma oryzae, Fusarium spp such as Fusarium semitectum (and/or moniliforme Gibberella fujikuroi (bakanae), Grainstaining complex (various pathogens), and/or Pythium ssp.
  • Helminthosporium. spp for example Helminthosporium oryzae, Microdochium oryzae, Pyricu- laria grisea (syn. Pyricularia oryzae), Rhizoctonia species, for example Rhizoctonia solani (syn in rice Pellicularia sasakii), Corticium sasakii and Ustilaginoidea virens.
  • the invention relates to methods according to the invention, applying mixtures comprising a compound of formula (I) as described above, in particular 1-1 -R, and at least one compound II which is metaaldehyde, in particular granular metaaldehyde.
  • the invention relates to methods according to the invention, applying mixtures comprising a compound of formula (I) as described above, in particular l-R-1 , and at least one compound II selected from the group of methiadinil, anthraquinones, beta-aminobu- tyric acid, laminarin, chitosan, thiamine and riboflavin.
  • the invention relates to methods according to the invention, applying mixtures comprising a compound of formula (I) as described above, in particular, in particular I- R-1 , and at least one compound II selected from the group of oxyenadenine (also called zeatin), kinetin (oxy)enadenine, brassinolides, insecticidal extracts of Celastrus angulatus, matrine, cnidiadin, tetramycin.
  • oxyenadenine also called zeatin
  • kinetin (oxy)enadenine kinetin (oxy)enadenine
  • brassinolides also called insecticidal extracts of Celastrus angulatus, matrine, cnidiadin, tetramycin.
  • the methods of the present invention comprise applying a mixture of at least one compound I of the present invention with at least one mixing partner II as defined above by seedling box application.
  • the invention relates to methods applying binary mixtures of one compound I with one mixing partner II as defined above as compo- nent II by seedling box application.
  • Preferred weight ratios for such binary mixtures are from 5000:1 to 1 :5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1 :100, particularly preferably from 10:1 to 1 :10.
  • components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.
  • the ingredients may be used sequentially or in combination with each other, if appropriate also added only immediately prior to use (tank mix).
  • the plant(s) may be sprayed with compound II either before or after being treated with compound I.
  • the invention relates to methods applying mixtures of one compound I with one mixing partner II, and optionally further pesticides by seedling box application.
  • the mixtures of the present invention are mixtures of a compound of formula (I), preferably l-R-1 , with a compound selected from the group of benomyl, carbendazim, epoxiconazole, fluquinconazole, flutriafol, flusilazole, metconazole, prochloraz, prothioconazole, tebuconazole, triticonazole, pyraclostrobin, trifloxystrobin, boscalid, dimetho- morph, penthiopyrad, dodemorph, famoxadone, fenpropimorph, proquinazid, pyrimethanil, tridemorph, maneb, mancozeb, metiram, thiram, chlorothalonil, dithianon, flusulfamide,met- rafenone, fluxapyroxad, bixafen, penflufen, sedaxane,
  • the mixtures of the present invention are mixtures of a compound of formula (I), preferably l-R-1 , with a compound selected from the group of imidaclo- prid, clothianidin, dinotefuran, chlorantraniliprole, cyantraniliprole, spinetoram, spinosad, ethiprole, fipronil, triflumezopyrim, flonicamid and tetraniliprole.
  • the mixtures of the present invention are mixtures of a compound of formula (I), preferably l-R-1 , with a compound selected from the group of probena- zole, isotianil, tricyclazole, pyroquilon, isoprothiolane, tolprocarb, carpropamid, diclocymet, azoxystrobin, orysastrobin.
  • the mixtures of the present invention are mixtures of a compound of formula (I), preferably l-R-1 , with a compound selected from the group of fu- rametpyr, thifluzamide, simeconazole, penflufen, azoxystrobin, orysastrobin,
  • M-227 l-R-1 diclocymet The mixtures of the present invention may be combined and applied in agriculture in mixture with further active ingredients, for example with other pesticides, insecticides, nematicides, fungicides, herbicides, safeners, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators.
  • mixtures are also embraced by the term “mixture(s) of the present invention” or “mixture ⁇ ) according to the invention.
  • Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers, and the like.
  • Preferred mixing partners are insecticides, nematicides and fungicides.
  • the invention relates to ternary mixtures, comprising a compound I, a compound II and one further compound III, which is not identical to the compound I or II already present in the mixture.
  • the invention relates to a mixture of
  • the invention relates to 4-way mixtures, comprising a compound I, a compound II and two further compounds III, which are not identical to the compound I or II already present in the mixture.
  • the invention relates to a mixture of
  • the invention relates to 5-way mixtures, comprising a compound I, a compound II and three further compounds III, which are not identical to the compound I or II already present in the mixture.
  • the invention also relates to methods, wherein the compounds of formula (I) are provided or applied in agrochemical compositions comprising an auxiliary and compound of formula (I) or a mixture thereof.
  • An agrochemical composition comprises a pesticidally effective amount of a compound of the present invention or a mixture thereof.
  • the term "pesticidally effective amount" is defined below.
  • compositions e.g. solutions, emulsions, suspensions, dusts, pow- ders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
  • compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifi- ers and binders.
  • suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifi- ers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclo ⁇ hexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil fractions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydronaphthalene, alkyl
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharide powders e.g. cellulose, starch
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul- fates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl-sul- fonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyhnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethox- ylated alcohols, or of fatty acid esters.
  • phosphates are phosphate esters. Exam- pies of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth-ox- ylates.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, 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 the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpoly- glucosides.
  • polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vi- nylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block pol- ymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of poly- acrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyeth- yleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present invention on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxilaries. Further 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), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli- nones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • composition types and their preparation are: i) Water-soluble concentrates (SL, LS)
  • a compound I according to the invention 10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to 100 wt%.
  • the active substance dissolves upon dilution with water.
  • a compound I according to the invention 5-25 wt% of a compound I according to the invention and 1 -10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.
  • dispersant e. g. polyvinylpyrrolidone
  • organic solvent e.g. cyclohexanone
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • 20-40 wt% water-insoluble organic solvent e.g. aromatic hydrocarbon
  • a compound I according to the invention 20-60 wt% of a compound I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 0,1 -2 wt% thickener e.g. xanthan gum
  • 50-80 wt% of a compound I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solu- tion of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • wt% of a compound I according to the invention are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dis- persion or solution of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1 -3 wt% wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • a compound I according to the invention In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. car- boxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active sub- stance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1 -5 wt% thickener e.g. car- boxymethylcellulose
  • 5-20 wt% of a compound I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alko- hol ethoxylate and arylphenol ethoxylate), and water up to 100 %.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alko- hol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methyl- methacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radi-cal initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase compris- ing 5-50 wt% of a compound I according to the invention, 0-40 wt% water insolu-ble organic solvent (e.g.
  • an isocyanate monomer e.g. diphenylme-thene-4,4'- diisocyanatae
  • a protective colloid e.g. polyvinyl alcohol
  • the addition of a polyamine results in the for-mation of a pol- yurea microcapsule.
  • the monomers amount to 1 -10 wt%. The wt% relate to the total CS com- position.
  • Dustable powders (DP, DS)
  • 1 -10 wt% of a compound I according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
  • 0.5-30 wt% of a compound I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.
  • solid carrier e.g. silicate
  • a compound I according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
  • organic solvent e.g. aromatic hydrocarbon.
  • compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.
  • auxiliaries such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably be- tween 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active sub-stance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions cormprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • a suspoconcentration is preferred for the application in crop protection.
  • the SC agrochemical composition comprises between 50 to 500 g/L (grams per Litre), or between 100 and 250 g/L, or 100 g/L or 150g/L or 200g/L or 250 g/L.
  • the granules according to formulation type xii are used for the application in rice according to the present invention.
  • dispersible concentrates DC according to formulation type ii are used for the application in rice according to the present invention.
  • the emulsifiable concentrates EC according to formulation type iii are used for the application in rice according to the present invention, ix. ME).
  • microemulsions ME according to formulation type ix are used for the application in rice according to the present invention.
  • nano-emulsions are used for the application in rice according to the present invention.
  • the user applies the composition according to the invention usually from a predosage de-vice, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • either individual components of the composition according to the in- vention or partially premixed components e. g. components comprising compounds of the present invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.
  • the invention also relates to methods, wherein the compounds of formula (I) are suitable for use in protecting rice, rice plants, rice plant propagation materials, such as seeds, or soil or water, in which the rice plants are growing, from attack or infestation by rice pests, especially rice pest invertebrates. Therefore, the present invention also relates to a plant protection methods, which comprises contacting rice, rice plants, rice plant propagation materials, such as seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by rice pests, especially rice pest invertebrates, with a pesticidally effective amount of a compound of the present invention.
  • the present invention also relates to a method of combating or controlling rice pests, especially rice pest invertebrates, which comprises contacting the rice pests, especially rice pest invertebrates, their habitat, breeding ground, or food supply, or the rice, rice plants, rice plant propagation materials, such as seeds, or soil or water, or the area, material or environment in which the rice pests, especially rice pest invertebrates, are growing or may grow, with a pesticidally effective amount of a compound of the present invention.
  • the compounds of the present invention are effective through both contact and ingestion.
  • the compounds of the present invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.
  • the compounds of the present invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions comprising said mixtures as defined above.
  • the components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture "in situ" on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
  • the application can be carried out both before and after the infestation of the rice, rice plants, rice plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.
  • Suitable application methods include inter alia soil treatment, seed treatment, in furrow appli- cation, water inlet application and foliar application.
  • Soil treatment methods include drenching the soil, dipping roots, or soil injection.
  • Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting.
  • furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying the pes- ticidally active compound to the furrow, and closing the furrow.
  • Foliar application refers to the application of the pesticidally active compound to plant foliage, e.g. through spray equipment.
  • pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and semiochemicals, such as http://www.pherobase.com.
  • Gramular application involves manual or mechanical scattering or throwing of insecticide granules or mixtures of insecticides/fungicides and nematicides, directly into a field or nursery box, either on the surface of the soil or on standing water.
  • the granular for- mulation may be mixed with a filler, carrier or fertilizer to allow for uniform distribution in the field.
  • Floating packet application refers to the application of an insecticide or mixtures of insecticides/fungicides and nematicides in a water soluble sachet/packet by throwing into the paddy field in standing water.
  • Seedling box application refers to manual or mechanical incorporation of insecticide formulations (for eg. Granules, liquid) in nursery boxes or seedling boxes containing rice seedlings before being transplanted into the main field.
  • insecticide formulations for eg. Granules, liquid
  • “Seed treatment” involves the soaking/mixing of rice seeds in a solution of an insecticide or insecticide/nematicide/fungicide mixture. This application is carried out before sowing, either before or after seed germination.
  • “Foliar application” refers to application of an insecticide or an insecticide/fungi- cide/nematicide/selective herbicides in water or oil as a spray application using various application equipment (eg. knapsack, power sprayer, boom sprayer, etc).
  • Soil application refers to the application of an insecticide or a mixture of an in- secticide/fungicide/nematicide/selective herbicide into the soil either as drench application, water inlet application or as a granular application.
  • Aerial application refers to the application of a granular or liquid application of an insecticide or a mixture of an insecticide/fungicide/nematicide/selective herbicide to the field using aeroplanes, helicopters or drones.
  • Dust application involves the directed application of an insecticide or a mixture of an insecticide/fungicide/nematicide/selective herbicide as a dust formulation using specialized applicators (eg. Power dusters) directly into the field.
  • specialized applicators eg. Power dusters
  • Water inlet application is the application of a liquid formulation of an insecticide or or a mixture of an insecticide/fungicide/nematicide/selective herbicide at the point where irrigation water is released into the paddy field.
  • Ending application is a type of application where a liquid or granular formulation of an insecticide or a mixture of an insecticide/fungicide/nematicide/selective herbicide is applied to standing water, in a clockwork or anti clockwork direction, to the inside borders of a paddy field.
  • Preferred applications are granular application, seedling box application and foliar application.
  • the invention relates to methods, in which the pesticide is applied by granular application.
  • the invention relates to methods, in which the pesticide is applied by seedling box application.
  • the invention relates to methods, in which the pesticide is applied by foliar application.
  • the term "contacting" or “applying” includes both direct contact (applying the compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus, i.e. habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant).
  • the term "animal pest” includes arthropods, gastropods, and nematodes, which are rice pests, especially rice pest invertebrates, especially rice pest insects as described above.
  • Arthropods are preferably insects and arachnids, in particular in- sects. Insects, which are of particular relevance, are typically referred to as crop insect pests or rice pest insects.
  • crop refers to both, growing and harvested rice.
  • the term "plant” means preferably rice plant (Oryza species, preferably Oryza sativa). Two species of rice are most frequently cultivated, Oryza sativa and Oryza glaberrima. Numerous subspecies of Oryza sativa are commercially important including Oryza sativa subsp. indica, Oryza sativa subsp. japonica, Oryza sativa subsp. javanica, Oryza sativa subsp. glutinosa (glutinous rice), Oryza sativa Aromatica group (e.g., basmati), and Oryza sativa (Floating rice group).
  • the term "plant” is to be understood as including wild type plants and plants, which have been modified by either conventional breeding, or mutagenesis or genetic engineering, or by a combination thereof.
  • Plants, which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include rice.
  • one or more genes have been mutagenized or integrated into the genetic material of the plant.
  • the one or more mutagenized or integrated genes are preferably selected from pat, epsps, crylAb, bar, cry1 Fa2, crylAc, cry34Ab1 , cry35AB1 , cry3A, cryF, cry1 F, mcry3a, cry2Ab2, cry3Bb1 , cry1A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asnl , and ppo5.
  • the mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant.
  • properties also known as traits, include abiotic stress tolerance, altered growth/yield, disease resistance, herbicide tolerance, insect resistance, modified product quality, and pollination control.
  • herbicide tolerance e.g. imidaz- olinone tolerance, glyphosate tolerance, or glufosinate tolerance
  • the pesticidal activity of the compounds of the present invention may be enhanced by the insecticidal trait of a modified plant.
  • the compounds of the present invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the present invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used.
  • plant propagation material refers to all the generative parts of the plant such as seeds, sprouted seeds, seedlings and ratooning. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, fruit, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.
  • pesticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the pesticidally effective amount can vary for the various compounds/compositions used in the invention.
  • a pesticidally effective amount of the compositions will also vary ac- cording to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
  • the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m 2 , preferably from 0.001 to 20 g per 100 m 2 .
  • the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40 to 50 g per hectare.
  • the compounds of the present invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling's roots and shoots against soil pests and foliar insects.
  • the present invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pregermina- tion with a compound of the present invention.
  • the protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling's shoots from piercing and sucking insects, chewing insects and nematodes.
  • seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods.
  • seed treatment application of the active compound is car- ried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
  • the present invention also comprises seeds coated with or containing the active compound.
  • coated with and/or containing generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.
  • the seed is seed of rice.
  • the active compounds of the invention may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action of herbicides or fungicides or insecticides. Such modified plants have been described in detail above.
  • Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter. Preferably, the formulations are applied such that germination is not included.
  • the active substance concentrations in ready-to-use formulations are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40 % by weight.
  • a FS formulation is used for seed treatment.
  • a FS formulation may comprise 1 -800 g/l of active ingredient, 1 -200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
  • Especially preferred FS formulations of the compounds of the present invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g.
  • a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
  • a binder sticker /adhesion agent
  • a preservative such as a biocide, antioxidant or the like
  • the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.
  • the invention therefore also relates to seed comprising a compound of the present invention, or an agriculturally useful salt thereof, as defined herein.
  • the amount of the compound of the present invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed.
  • the compounds of the present invention may also be used for improving the health of a plant. Therefore, the present invention also relates to a method for improving plant health by treating a rice plant, rice plant propagation material and/or the locus where the rice plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the present invention.
  • an effective and non-phytotoxic amount means that the compound is used in a quantity which allows to obtain the desired effect but which does not give rise to any phyto- toxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil.
  • plant and “plant propagation material” are defined above.
  • Plant health is defined as a condition of the plant and/or its products which is determined by several aspects alone or in combination with each other such as yield (for example increased biomass and/or increased content of valuable ingredients), quality (for example improved content or composition of certain ingredients or shelf life), plant vigour (for example improved plant growth and/or greener leaves ("greening effect"), tolerance to abiotic (for example drought) and/or biotic stress (for example disease) and production efficiency (for example, harvesting efficiency, processability).
  • yield for example increased biomass and/or increased content of valuable ingredients
  • quality for example improved content or composition of certain ingredients or shelf life
  • plant vigour for example improved plant growth and/or greener leaves ("greening effect")
  • tolerance to abiotic for example drought
  • biotic stress for example disease
  • production efficiency for example, harvesting efficiency, processability
  • the above identified indicators for the health condition of a plant may be interdependent and may result from each other.
  • Each indicator is defined in the art and can be determined by meth- ods known to a skilled person.
  • N-Methoxymethanamine hydrochloride (345g) and water (1 .5 L) were cooled to 0°C.
  • K2CO3 1466g
  • methyl tert-butyl ether 1000 ml.
  • the reaction mixture was cooled to -5 °C.
  • Chloroacetylchloride 400 g
  • methyl tert-butyl ether 500 ml
  • the reaction mixture was allowed to come to 20-25°C. From the organic layer, the desired product was obtained as white solid (438g, 90 % yield; 98.45% HPLC purity).
  • Step 3 N-[2-chloro-1 -(2-chlorothiazol-5-yl) ethylidene]-2-methyl-propane-2-sulfinamide
  • 2-chloro-1 -(2-chlorothiazol-5-yl) ethanone 335 g
  • tert-butyl sulfinamide 396 ml
  • Ti(OEt) 4 396 ml
  • the mixture was heated to 50 °C and stirred for 2 hours, then cooled to 20-25°C and diluted with ethyl acetate. After adding water, the mixture was stirred for 30 minutes, then filtered.
  • the organic phase was evaporated to obtain the desired crude product as brown colored oil. After treatment with activated charcoal and silica in methyl tert-butyl ether, the crude product was obtained as pale brown colored oil (365 g) for direct use in the next step.
  • Step 4 N-[2-chloro-1 -(2-chlorothiazol-5-yl) ethyl]-2-methyl-propane-2-sulfinamide
  • N-[2-chloro-1 -(2-chlorothiazol-5-yl) ethyl]-2-methyl-propane-2-sulfinamide was stirred with HCI in methanole (1 molar, 620 ml.) at 20-25°C for 12 hours. Removal of methanole under vacuum yielded a pale yellow sticky solid (244 g), which was washed with methyl tert-butyl ether and subsequently with ethyl acetate to get a pale yellow color solid (78 g, 26 % yield over steps 2 to 5, >98% purity).
  • Step 7 3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a] pyrimidin-8- ium-5-olate (1-1 )
  • Racemic material was dissolved in mixed solution of MeOH-CHsCN-DCM (1 :1 :0.5) to 20 mg/mL and filtrated through membrane with pore sized 0.45um.
  • Table 1 Efficacy of 1-1 against rice water weevil (Lissorhoptrus oryzophilus) by granular seed- ling box application

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Abstract

La présente invention concerne des procédés de lutte contre les invertébrés nuisibles du riz, lesquels procédés comprennent l'application de composés de pyrimidinium de formule (I), des stéréo-isomères, des sels, des tautomères et des N-oxydes de ceux-ci, leurs mélanges et des compositions comprenant de tels composés ou mélanges, par application en boîte de semis.
PCT/EP2018/073516 2017-08-31 2018-08-31 Procédé de lutte contre les nuisibles du riz dans le riz WO2019043183A1 (fr)

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US11399543B2 (en) 2017-10-13 2022-08-02 Basf Se Substituted 1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidiniumolates for combating animal pests

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CN110678469B (zh) 2017-06-19 2023-03-03 巴斯夫欧洲公司 用于防除动物害虫的取代嘧啶鎓化合物和衍生物
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