WO2010094728A1 - Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance - Google Patents

Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance Download PDF

Info

Publication number
WO2010094728A1
WO2010094728A1 PCT/EP2010/052018 EP2010052018W WO2010094728A1 WO 2010094728 A1 WO2010094728 A1 WO 2010094728A1 EP 2010052018 W EP2010052018 W EP 2010052018W WO 2010094728 A1 WO2010094728 A1 WO 2010094728A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
methyl
unsubstituted
alkoxy
amino
Prior art date
Application number
PCT/EP2010/052018
Other languages
French (fr)
Inventor
Pierre-Yves Coqueron
Daniela Portz
Ulrike Wachendorff-Neumann
Original Assignee
Bayer Cropscience Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Priority to JP2011550559A priority Critical patent/JP2012518028A/en
Priority to EP10706189A priority patent/EP2398326A1/en
Priority to US13/202,200 priority patent/US20120027741A1/en
Publication of WO2010094728A1 publication Critical patent/WO2010094728A1/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms

Definitions

  • the present invention relates to a pesticide composition intended for protecting plants, crops or seeds against fungal diseases or insect damages, and the corresponding methods of protection by application of the said composition. More precisely, the subject of the present invention is a pesticide composition based on a tetrazolyloxime derivative and a fungicide or an insecticide active substance or compound.
  • the present invention provides a pesticide composition which can be used, in particular by the farmer, for controlling the pest infesting crops and in particular for controlling insects or diseases.
  • the pesticide compounds useful for the protection of plants must be endowed with an ecotoxicity which is reduced to the minimum. As far as possible, they should not be dangerous or toxic to the operator during use. The economic factor should of course not be overlooked in the search for novel pesticide agents.
  • the present invention advantageously provides a pesticide composition which is completely high-performing in particular as regards its efficacy against pests and the perennially of this efficacy so as to be able to reduce the doses of chemical products spread in the environment for combating pest damages or attacks of plants or crops.
  • the invention provides a pesticide composition capable to be more active and active for longer, and which therefore has a lower dose, but which is also less toxic, in particular in the treatment of plants and particularly the foliar and seed treatments of fungal diseases or the control of insects, for example, of cereals, cotton, peanut, bean, beet, canola, Solanaceae, grapevine, vegetables, lucerne, soybean, market garden crops, turf, wood or horticultural plants.
  • the composition according to the invention allows controlling a broad variety of insects or fungi.
  • the pesticide composition according to the invention exhibits an improved efficacy against fungus like Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Basidiomycetes, Deuteromycetes and Ascomycetes. All these objectives or advantages, among others, were achieved by finding a pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide compound. Such a composition surprisingly and unexpectedly allows a very high and perennial anti-fungal or insecticide efficacy against a broad spectrum of insects or fungi and in particular against those responsible for diseases or damages of crops. Other insect pests or diseases of crops can be controlled with the pesticide composition according to the invention.
  • the pesticide composition according to the invention may also be used for the treatment of bacterial or virus diseases. Insects or nematodes that can be controlled with the pesticide composition according to the invention include a broad variety of these damaging organisms.
  • the present invention provides a composition comprising: A) a tetrazolyloxime derivative of formula (I)
  • R 1 represents a hydrogen atom, a halogen atom, a substituted or non-substituted Ci-C 6 - alkyl, a substituted or non-substituted d-C 6 -alkoxy, nitro, cyano, a substituted or non- substituted d-C 6 -aryl or a substituted or non-substituted d-C 6 -alkylsulphonyl;
  • A represents a tetrazoyl group of formula (A 1 ) or (A 2 ):
  • R 2 and R 3 independently represent a hydrogen atom, a halogen atom, a substituted or non-substituted Ci-C 8 -alkyl, nitro, cyano, a hydroxy group, a mercapto group, formyl, hydroxycarbonyl, a substituted or non-substituted amino, a substituted or non-substituted C 2 -C 8 -alkenyl, a substituted or non-substituted C 2 -C 8 -alkynyl, a substituted or non-substituted aryl, a substituted or non-substituted heterocyclyl, OR a , S(O) r R a , C0R a or C0 2 R a ; wherein R a represents a substituted or non-substituted C 1 -C 8 - alkyl, a substituted or non-substituted
  • Z represents Q 1 CONH- , wherein Q 1 represents a substituted or non-substituted Ci-C 8 - haloalkyl comprising between one and 9 halogen atoms, a substituted or non- substituted C 2 -C 8 -haloalkenyl comprising between one and 9 halogen atoms, a substituted or non-substituted C 2 -C 8 -alkynyl, a substituted or non-substituted C 2 -C 8 - haloalkynyl comprising between one and 9 halogen atoms, a substituted or non- substituted Ci-C 8 -haloalkoxy comprising between one and 9 halogen atoms, , a substituted or non-substituted C 2 -C 8 -alkenyloxy, a substituted or non-substituted C 2 -C 8 -alkenyloxy, a substituted or non-substituted C
  • C-rCs-alkylannino C- ⁇ -C 8 -alkoxy substituted with a substituted or unsubstituted aralkylamino, an aryloxy, d-C 8 -alkyl substituted with a carboxyl residue, d-C 8 -alkyl substituted with a substituted or unsubstituted aralkylamino, d-C 8 -alkyl substituted with a substituted or unsubstituted aryloxy, d-C 8 -alkyl substituted with an acyl group, C 1 -C 8 - alkyl substituted with a substituted or unsubstituted heterocyclyl group;
  • Z represents a hydrogen atom, an amino or Q 2 CONH-, wherein Q 2 represents a hydrogen atom, a substituted or non-substituted Ci-C 8 -haloalkyl comprising between one and 9 halogen atoms, a substituted or non-substituted C 2 -C 8 -alkenyl, a substituted or non-substituted C 2 -C 8 -haloalkenyl comprising between one and 9 halogen atoms, a substituted or non- substituted C 2 -C 8 -alkynyl, a substituted or non-substituted C 2 -C 8 -haloalkynyl comprising between one and 9 halogen atoms, a substituted or non-substituted Ci-C 8 -alkoxy, a substituted or non-substituted Ci-C 8 -haloalk
  • n 2 or 3 and when R 2 or R 3 independently represents a hydroxy group, a mercapto group, a non-substituted d-C 8 -alkyl, nitro, cyano, formyl, hydroxycarbonyl, a substituted or non-substituted amino, a substituted or non- substituted C 2 -C 8 -alkenyl, a substituted or non-substituted C 2 -C 8 -alkynyl, a substituted or non-substituted aryl, a substituted or non-substituted heterocyclyl, OR a , S(O) r R a , C0R a or CO 2 R 3 , R a being herein-defined or when n represents 3 and when R 2 represents a halogen atom, Z represents a hydrogen atom, an amino or Q 3 CONH- , wherein Q 3 represents a hydrogen atom, a substituted or non
  • Ci-C 8 -alkyl substituted with a substituted or unsubstituted amino Ci-C 8 -alkyl substituted with a substituted or unsubstituted aryloxy, a Ci-C 8 -alkyl substituted with a substituted or unsubstituted Ci-C 8 -alkylthio, a Ci-C 8 -alkyl substituted with a substituted or unsubstituted Ci-C 8 -alkoxy, Ci-C 8 -alkyl substituted with an acyl group, Ci-C 8 -alkyl substituted with a substituted or unsubstituted heterocyclyl group;
  • any of the compounds according to the invention can exist as one or more stereoisomers depending on the number of stereogenic units (as defined by the IUPAC rules) in the compound.
  • the invention thus relates equally to all the stereoisomers, and to the mixtures of all the possible stereoisomers, in all proportions.
  • the stereoisomers can be separated according to the methods which are known per se by the man ordinary skilled in the art.
  • the stereostructure of the oxime moiety present in the heterocyclyloxime derivative of formula (I) includes (E) or (Z) isomer, and these stereoisomers form part of the present invention.
  • halogen means fluorine, chlorine, bromine or iodine ;
  • heteroatom can be nitrogen, oxygen or sulphur ;
  • a group or a substituent that is substituted according to the invention can be substituted by one or more of the following groups or atoms: a halogen atom, a nitro group, a hydroxy group, a cyano group, an isocyano group, an isocyanate group, an thiocyanate group, an amino group, a sulphenyl group, a formyl group, a formyloxy group, a carbamoyl group, a Ci-C 8 -alkyl, a Ci-C 8 - halogenoalkyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 2 -C 8 - alkenyloxy, a Ci-C 8 -alkylamino, a di-Ci-C 8 -alkylamino, a phenylamino, a benz
  • heterocyclyl means saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl.
  • the present invention provides a composition comprising:
  • the present invention provides a composition comprising:
  • composition comprising:
  • composition comprising:
  • R 1 represents preferentially a hydrogen atom, a halogen atom, a substituted or non- substituted Ci-C 6 -alkyl, a substituted or non-substituted d-C 6 -alkoxy.
  • the alkyl group represented for R 1 is preferably an alkyl group having 1 to 4 carbon atoms and specific examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.
  • a methyl group or a tert-butyl group is particularly preferred.
  • the d-C 6 -alkoxy group for R 1 is preferably alkoxy group having 1 to 3 carbon atoms and specific examples thereof include a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group. Among these alkoxy groups, a methoxy group or an ethoxy group is particularly preferred.
  • R 1 represents more preferentially a hydrogen atom or a halogen atom.
  • Y represents an alkyl group.
  • alkyl groups an alkyl group having 1 to 3 carbon atoms such as a methyl group, an ethyl group, a n- propyl group or an isopropyl group is preferable.
  • a methyl group is particularly preferred.
  • R 2 and R 3 independently represent preferentially a hydrogen atom or a halogen atom.
  • the stereostructure of the oxime moiety present in the tetrazolyloxime derivative of formula (I) includes (E) or (Z) isomer, and these stereoisomers form part of the present invention.
  • the synthesized product is generally obtained in the form of the (Z) isomer or a mixture of (E) and (Z) isomers, each of which can be isolated by separation or purification.
  • the (Z) isomer is particularly superior to the (E) isomer in plant disease controlling activity.
  • both the (E) isomer and the (Z) isomer generally exist in a fixed ratio in the form of a mixture since the (Z) isomer is generally converted into the (E) isomer by light in a natural environment.
  • the stable ratios of the (E) and (Z) isomers vary according to the type of compound.
  • fungicide compounds B and C can be independently selected in the list L1 consisting of:
  • Inhibitors of the ergosterol biosynthesis for example (1.1 ) aldimorph (1704-28-5), (1.2) azaconazole (60207-31-0), (1.3) bitertanol (55179-31-2), (1.4) bromuconazole (116255-48-2), (1.5) cyproconazole (113096-99-4), (1.6) diclobutrazole (75736-33-3), (1.7) difenoconazole (119446-68-3), (1.8) diniconazole (83657-24-3), (1.9) diniconazole-M (83657-18-5), (1.10) dodemorph (1593-77-7), (1.1 1 ) dodemorph acetate (31717-87-0), (1.12) epoxiconazole (106325-08-0), (1.13) etaconazole (60207-93-4), (1.14) fenarimol (60168-88-9), (1.15) fenbuconazole (114369-43-6
  • inhibitors of the respiratory chain at complex I or II for example (2.1 ) bixafen (581809-46- 03), (2.2) boscalid (188425-85-6), (2.3) carboxin (5234-68-4), (2.4) diflumetorim (130339-07-0), (2.5) fenfuram (24691-80-3), (2.6) fluopyram (658066-35-4), (2.7) flutolanil (66332-96-5), (2.8) furametpyr (123572-88-3), (2.9) furmecyclox (60568-05-0), (2.10) isopyrazam (mixture of syn- epimeric racemate 1 RS,4SR,9RS and anti-epimeric racemate 1 RS,4SR,9SR) (881685-58-1 ), (2.1 1 ) isopyrazam (anti-epimeric racemate 1 RS,4SR,9SR), (2.12) isopyrazam (anti-epimeric enantiomer 1 R
  • inhibitors of the respiratory chain at complex III for example (3.1 ) amisulbrom (348635-87- 0), (3.2) azoxystrobin (131860-33-8), (3.3) cyazofamid (120116-88-3), (3.4) dimoxystrobin (141600-52-4), (3.5) enestroburin (238410-1 1-2) (known from WO 2004/058723), (3.6) famoxadone (131807-57-3) (known from WO 2004/058723), (3.7) fenamidone (161326-34-7) (known from WO 2004/058723), (3.8) fluoxastrobin (361377-29-9) (known from WO 2004/058723), (3.9) kresoxim-methyl (143390-89-0) (known from WO 2004/058723), (3.10) metominostrobin (133408-50-1 ) (known from WO 2004/058723), (3.11 ) orysa
  • Inhibitors of the mitosis and cell division for example (4.1 ) benomyl (17804-35-2), (4.2) carbendazim (10605-21-7), (4.3) chlorfenazole (3574-96-7), (4.4) diethofencarb (87130-20-9),
  • Inhibitors of the amino acid and/or protein biosynthesis for example (7.1 ) andoprim (23951- 85-1 ), (7.2) blasticidin-S (2079-00-7), (7.3) cyprodinil (121552-61-2), (7.4) kasugamycin (6980- 18-3), (7.5) kasugamycin hydrochloride hydrate (19408-46-9), (7.6) mepanipyrim (110235-47-7) and (7.7) pyrimethanil (53112-28-0).
  • Inhibitors of the ATP production for example (8.1 ) fentin acetate (900-95-8), (8.2) fentin chloride (639-58-7), (8.3) fentin hydroxide (76-87-9), (8.4) and silthiofam (175217-20-6).
  • Inhibitors of the cell wall synthesis for example (9.1 ) benthiavalicarb (177406-68-7), (9.2) dimethomorph (110488-70-5), (9.3) flumorph (211867-47-9), (9.4) iprovalicarb (140923-17-7), (9.5) mandipropamid (374726-62-2), (9.6) polyoxins (11 113-80-7), (9.7) polyoxorim (22976-86- 9), (9.8) validamycin A (37248-47-8) and (9.9) valifenalate (283159-94-4; 283159-90-0).
  • Inhibitors of the lipid and membrane synthesis for example (10.1 ) biphenyl (92-52-4), (10.2) chloroneb (2675-77-6), (10.3) dicloran (99-30-9), (10.4) edifenphos (17109-49-8), (10.5) etridiazole (2593-15-9), (10.6) iodocarb (55406-53-6), (10.7) iprobenfos (26087-47-8), (10.8) isoprothiolane (50512-35-1 ), (10.9) propamocarb (25606-41-1 ), (10.10) propamocarb hydrochloride (25606-41-1 ), (10.11 ) prothiocarb (19622-08-3), (10.12) pyrazophos (13457-18- 6), (10.13) quintozene (82-68-8), (10.14) tecnazene (117-18-0) and (10.15) tolclofos-methyl (57018-04-9).
  • Inhibitors of the melanine biosynthesis for example (11.1 ) carpropamid (104030-54-8), (11.2) diclocymet (139920-32-4), (11.3) fenoxanil (115852-48-7), (1 1.4) phthalide (27355-22-2), (11.5) pyroquilon (57369-32-1 ) and (11.6) tricyclazole (41814-78-2).
  • Inhibitors of the nucleic acid synthesis for example (12.1 ) benalaxyl (71626-11-4), (12.2) benalaxyl-M (98243-83-5), (12.3) bupirimate (41483-43-6), (12.4) clozylacon (67932-85-8), (12.5) dimethirimol (5221-53-4), (12.6) ethirimol (23947-60-6), (12.7) furalaxyl (57646-30-7),
  • Inhibitors of the signal transduction for example (13.1 ) chlozolinate (84332-86-5), (13.2) fenpiclonil (74738-17-3), (13.3) fludioxonil (131341-86-1 ), (13.4) iprodione (36734-19-7), (13.5) procymidone (32809-16-8), (13.6) quinoxyfen (124495-18-7) and (13.7) vinclozolin (50471-44- 8).
  • preferred fungicide compounds B and C are independently selected in the list L2 consisting of ametoctradin, azoxystrobin, benalaxyl-M, benthiavalicarb, bixafen also known as N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-3- (difluoromethyl)-1-methyl-1 H-pyrazole-4-carboxamide, boscalid, chlorothalonil, copper hydroxide, copper oxychloride, cyazofamid, cymoxanil, dimethomorph, epoxiconazole, famoxadone, fenamidone, fenhexamid, fluazinam, fludioxonil, fluopicolide, fluopyram also known as N- ⁇ 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl ⁇ -2
  • this invention is directed to mixtures comprising at least the compound A [but-3-yn-1-yl ⁇ 6-[( ⁇ [(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino ⁇ - oxy)methyl]pyridin-2-yl ⁇ carbamate] and one fungicide compound selected from the compounds listed in List L1.
  • this invention is directed to mixtures comprising at least the compound A and one fungicide compound selected from the compounds listed in List L2.
  • insecticide compound D is preferably selected in the list L3 consisting of:
  • Acetylcholinesterase (AChE) inhibitors for example carbamates, e.g. alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thio- fanox, triazamate, trimethacarb, XMC, and xylylcarb; or organophosphates, e.g.
  • GABA-gated chloride channel antagonists for example organochlorines, e.g. chlordane, endosulfan (alpha-); or fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, pyrafluprole, and pyriprole.
  • organochlorines e.g. chlordane, endosulfan (alpha-); or fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, pyrafluprole, and pyriprole.
  • Sodium channel modulators/voltage-dependent sodium channel blockers for example pyrethroids, e.g. acrinathrin, allethrin (d-cis-trans, d-trans), bifenthrin, bioallethrin, bioallethrin S- cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin (beta-), cyhalothrin (gamma-, lambda-), cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin [(I R)-trans-isomers], deltamethrin, dimefluthrin, empenthrin [(EZ)-(I R)-isomers), esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethr
  • Nicotinergic acetylcholine receptor agonists for example chloronicotinyls, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam,; or nicotine..
  • Allosteric acetylcholine receptor modulators for example spinosyns, e.g. spinetoram and spinosad.
  • Chloride channel activators for example avermectins/milbemycins, e.g. abamectin, emamectin benzoate, lepimectin, and milbemectin.
  • Juvenile hormone mimics e.g. hydroprene, kinoprene, methoprene; or fenoxycarb; pyriproxyfen.
  • Miscellaneous non-specific (multi-site) inhibitors for example gassing agents, e.g. methyl bromide and other alkyl halides; or chloropicrin; sulfuryl fluoride; borax; tartar emetic.
  • gassing agents e.g. methyl bromide and other alkyl halides; or chloropicrin; sulfuryl fluoride; borax; tartar emetic.
  • D9 Selective homopteran feeding blockers, e.g. pymetrozine; or flonicamid.
  • Mite growth inhibitors e.g. clofentezine, diflovidazin, hexythiazox, etoxazole.
  • D11 Microbial disruptors of insect midgut membranes, e.g.
  • Inhibitors of mitochondrial ATP synthase for example diafenthiuron; or organotin miticides, e.g. azocyclotin, cyhexatin, and fenbutatin oxide; or propargite; tetradifon.
  • Nicotinic acetylcholine receptor channel blockers for example bensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.
  • Inhibitors of chitin biosynthesis type 0, for example benzoylureas, e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, and triflumuron.
  • benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, and triflumuron.
  • D16 Inhibitors of chitin biosynthesis, type 1 , for example buprofezin.
  • Ecdysone receptor agonists/disruptors for example diacylhydrazines, e.g. chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.
  • D19 Octopamine receptor agonists, for example amitraz.
  • D20 Mitochondrial complex III electron transport inhibitors (Coupling site II), for example hydramethylnon; acequinocyl; fluacrypyrim; or cyflumetofen and cyenopyrafen.
  • Coupling site II for example hydramethylnon; acequinocyl; fluacrypyrim; or cyflumetofen and cyenopyrafen.
  • METI acaricides e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; or rotenone.(Derris).
  • (D23) Inhibitors of acetyl CoA carboxylase for example tetronic acid derivatives, e.g. spirodiclofen and spiromesifen; or tetramic acid derivatives, e.g. spirotetramat.
  • tetronic acid derivatives e.g. spirodiclofen and spiromesifen
  • tetramic acid derivatives e.g. spirotetramat.
  • Mitochondrial complex IV electron inhibitors for example phosphines, e.g. aluminium phosphide, calcium phosphide, phosphine, and zinc phosphide; or cyanide.
  • Ryanodine receptor modulators for example diamides, e.g. chlorantraniliprole (Rynaxypyr), Cyantraniliprole (Cyazypyr), and flubendiamide.
  • Further active ingredients with unknown or uncertain mode of action for example azadirachtin, amidoflumet, benzoximate, bifenazate, chinomethionat, cryolite, dicofol, flufenerim, pyridalyl, and pyrifluquinazon; or one of the following known active compounds
  • insecticide compounds are selected in the list L4 consisting of imidacloprid and clothianidin.
  • this invention is directed to mixtures comprising at least the compound A [but-3-yn-1-yl ⁇ 6-[( ⁇ [(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino ⁇ - oxy)methyl]pyridin-2-yl ⁇ carbamate] and one insecticidal compound selected from the compounds listed in List L3.
  • this invention is directed to mixtures comprising at least the compound A and one insecticidal compound selected from the compounds listed in List L4.
  • the A/B weight ratio preferably ranges from 1/0.01 to 1/100; more preferably from 1/0.05 to 1/80.
  • the A/B/C or A/B/D weight ratio preferably ranges from 1/0.01/0.01 to 1/100/100; more preferably from 1/0.05/0.05 to 1/80/80.
  • the A/B/C/D weight ratio preferably ranges from 1/0.01/0.01/0.1 to 1/100/100/100; more preferably from 1/0.05/0.05/0.5 to 1/80/80/80.
  • compositions according to the invention are defined as combining all or part of:
  • the compound ratio A/B in the pesticide composition according to the invention, can be advantageously selected so as to produce a synergistic effect.
  • synergistic effect is understood to mean in particular that defined by Colby in an article entitled “Calculation of the synergistic and antagonistic responses of herbicide combinations" Weeds, (1967), 15, pages 20-22. The latter article mentions the formula: XY
  • E represents the expected percentage of inhibition of the pest for the combination of the two compounds at defined doses (for example equal to x and y respectively)
  • X is the percentage of inhibition observed for the pest by compound A at a defined dose (equal to x)
  • Y is the percentage of inhibition observed for the pest by compound B at a defined dose (equal to y).
  • the compound ratio A/B/C can be advantageously selected so as to produce a synergistic effect.
  • synergistic effect is understood to mean in particular that defined by Colby in an article entitled “Calculation of the synergistic and antagonistic responses of herbicide combinations" Weeds, (1967), 15, pages 20-22. The latter article mentions the formula:
  • E X + Y + Z- ⁇ - 100
  • E represents the expected percentage of inhibition of the pest for the combination of the three compounds at defined doses (for example equal to x, y and z respectively)
  • X is the percentage of inhibition observed for the pest by compound A at a defined dose (equal to x)
  • Y is the percentage of inhibition observed for the pest by compound B at a defined dose (equal to y)
  • Z is the percentage of inhibition observed for the pest by compound C at a defined dose (equal to z).
  • E represents the expected percentage of inhibition of the pest for the combination of the three compounds at defined doses (for example equal to x, y and z respectively)
  • X is the percentage of inhibition observed for the pest by compound A at a defined dose (equal to x)
  • Y is the percentage of inhibition observed for the pest by compound B at a defined dose (equal to y)
  • Z is the percentage of inhibition observed for the pest by compound C at a defined dose (equal to z).
  • Synergistic compositions comprising further active substances also form part of the present invention, the associated synergistic effect can be evidenced in a similar manner.
  • the pesticide composition according to the invention may comprise from 0.00001 to 100%, preferably from 0.001 to 80%, of active compounds, whether these compounds are combined or whether they are in the form of two or more active ingredients used separately. More generally, the pesticide composition according to the invention may eventually also comprise one or more other active substances selected from fungicide, herbicide, insecticide or plant growth regulator active compounds.
  • the pesticide composition according to the invention may also comprise any other adjuvants or auxiliary agent useful in plant protection formulations such as, for example, an agriculturally suitable inert carrier and optionally an agriculturally suitable surfactant.
  • the pesticide composition according to the invention can be used alone or in formulations containing one or the other of the active ingredients or alternatively both of them together, in combination or association with one or more other compatible components which are, for example, solid or liquid fillers or diluents, adjuvants, surfactants or equivalents, which are suitable for the desired use and which are acceptable for uses in agriculture.
  • the formulations can be of any type known in the sector that is suitable for application onto all types of cultures or crops. These formulations, which can be prepared in any manner known by the skilled person, also form part of the invention.
  • the formulations may also contain ingredients of other types, such as protective colloids, adhesives, thickeners, thixotropic agents, penetrating agents, oils for spraying, stabilisers, preserving agents (in particular mould-proofing or biocide agents), sequestering or chelating agents or the like. More generally, the compounds used in the invention can be combined with any solid or liquid additives corresponding to the usual formulation techniques.
  • filler means an organic or inorganic, natural or synthetic component with which the active components are combined to facilitate its application, for example, onto the plants, the seeds or the soil.
  • This filler is consequently generally inert and it must be acceptable (for example acceptable for agronomic uses, in particular for treating plants).
  • the filler can be solid, for example clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers (for example ammonium salts), natural soil minerals, such as kaolins, clays, talc, lime, quartz, attapulgite, montmorillonite, bentonite or diatomaceous earths or synthetic minerals, such as silica, alumina or silicates, in particular aluminium or magnesium silicates.
  • the solid fillers which are suitable for granules are as follows: natural, crushed or broken rocks, such as calcite, marble, pumice, sepiolite and dolomite; synthetic granules of inorganic or organic flours; granules of organic material such as sawdust, coconut shell, corn ear or envelope or tobacco stem; kieselguhr, tricalcium phosphate, powdered cork or adsorbent carbon black; water-soluble polymers, resins, waxes; or solid fertilizers.
  • Such composition may, if so desired, contain one or more compatible agents such as wetting agents, dispersing agents, emulsifiers or colourings which, when they are solid, may also act as diluents.
  • the fillers may also be liquid, for example: water, alcohols, in particular butanol or glycol, as well as ethers or esters thereof, in particular methyl glycol acetate; ketones, in particular acetone, cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone or isophorone; petroleum fractions such as paraffinic or aromatic hydrocarbons, in particular xylenes or alkylnaphthalenes; mineral or plant oils; aliphatic chlorohydrocarbons, in particular trichloroethane or methylene chloride; aromatic chlorohydrocarbons, in particular chlorobenzenes; water-soluble or highly polar solvents such as dimethylformamide, dimethyl sulphoxide, N,N-dimethyl-acetamide or N- methylpyrrolidone; N-octylpyrrolidone, liquefied gases; or the like, whether they are taken separately or as a mixture.
  • the surfactant can be an emulsifier, a dispersing agent or a wetting agent, of ionic or nonionic type or a mixture of these surfactants.
  • surfactants there are used, for example, polyacrylic acid salts, lignosulphonic acid salts, phenolsulphonic or naphthalenesulphonic acid salts, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty esters or fatty amines, substituted phenols (in particular alkylphenols or arylphenols), ester-salts of sulphosuccinic acid, taurine derivatives (in particular alkyl taurates), phosphoric esters of alcohols or of polycondensates of ethylene oxide with phenols, fatty acid esters with polyols or sulphate, sulphonate or phosphate functional derivatives of the compounds described above.
  • the presence of at least one surfactant is generally essential when the active ingredients and/or the in
  • the formulations may also contain other additives such as adhesives or dyes.
  • Adhesives such as carboxymethylcellulose or natural or synthetic polymers in the form of powders, granules or matrices, such as gum arabic, latex, polyvinylpyrrolidone, polyvinyl alcohol or polyvinyl acetate, natural phospholipids, such as cephalins or lecithins or synthetic phospholipids can be used in the formulations.
  • colourings such as inorganic pigments, such as, for example: iron oxides, titanium oxides, Prussian blue; organic colouring stuffs, such as those of the alizarin, azo or metal phthalocyanin type; or of trace elements such as iron, manganese, boron, copper, cobalt, molybdenum or zinc salts.
  • inorganic pigments such as, for example: iron oxides, titanium oxides, Prussian blue
  • organic colouring stuffs such as those of the alizarin, azo or metal phthalocyanin type
  • trace elements such as iron, manganese, boron, copper, cobalt, molybdenum or zinc salts.
  • the pesticide composition according to the present invention covers not only the compositions which are ready to be applied to the crop by means of a suitable device, such as a spraying device, but also the commercial concentrated composition which have to be diluted before application to the crop.
  • the pesticide composition herein described is used in general for application to growing plants or to sites where crops are grown or intended to grow or for the treatment, coating or film- coating of seeds.
  • seeds may comprise any propagation materials, like for example seeds, fruit, tubers, grains, roots, rhizomes, parts of plants.
  • the pesticide composition according to the invention may also be applied to the vegetation and in particular to the leaves infested or capable of being infested with the phytopathogenic fungi or damaged by insects.
  • Another method of applying the pesticide composition according to the invention is to add a formulation containing the active ingredients to the irrigation water.
  • a method for controlling the phytopathogenic fungi or damaging insects of plants, crops or seeds characterized in that an agronomically effective and substantially non-phytotoxic quantity of a pesticide composition according to the invention is applied as seed treatment, foliar application, stem application, drench or drip application (chemigation) to the seed, the plant or to the fruit of the plant or to soil or to inert substrate (e.g. inorganic substrates like sand, rockwool, glasswool; expanded minerals like perlite, vermiculite, zeolite or expanded clay), Pumice, Pyroclastic materials or stuff, synthetic organic substrates (e.g. polyurethane) organic substrates (e.g.
  • the method according to the invention may either be a curing, preventing or eradicating method.
  • a composition used can be prepared beforehand by mixing the two or more active compounds according to the invention.
  • compositions each containing one or more active ingredients (A), (B),
  • - for foliar treatments from 0.1 to 10,000 g/ha, preferably from 10 to 1 ,000 g/ha, more preferably from 50 to 300g/ha; in case of drench or drip application, the dose can even be reduced, especially while using inert substrates like rockwool or perlite;
  • - for seed treatment from 2 to 200 g per 100 kilogram of seed, preferably from 3 to 15O g per 100 kilogram of seed;
  • - for soil treatment from 0.1 to 10,000 g/ha, preferably from 1 to 5,000 g/ha.
  • the doses herein indicated are given as illustrative Examples of method according to the invention.
  • a person skilled in the art will know how to adapt the application doses, notably according to the nature of the plant or crop to be treated. Under specific conditions, for example according to the nature of the phytopathogenic fungus to be treated or insect to control, a lower dose may offer adequate protection. Certain climatic conditions, resistance or other factors like the nature of the phytopathogenic fungi or damaging insect to be eliminated or the degree of infestation, for example, of the plants with these fungi, may require higher doses of combined active ingredients. The optimum dose usually depends on several factors, for example on the type of phytopathogenic fungus to be treated or insect to control, on the type or level of development of the infested plant, on the density of vegetation or alternatively on the method of application.
  • the crop treated with the pesticide composition or combination according to the invention is, for example, grapevine, but this could be cereals, vegetables, lucerne, soybean, market garden crops, turf, wood, tree or horticultural plants.
  • the method of treatment according to the invention may also be useful to treat propagation material such as tubers or rhizomes, but also seeds, seedlings or seedlings pricking out and plants or plants pricking out. This method of treatment may also be useful to treat roots.
  • the method of treatment according to the invention may also be useful to treat the over-ground parts of the plant such as trunks, stems or stalks, leaves, flowers and fruit of the concerned plant.
  • the plants that may becan be protected by the method according to the invention mention may becan be made of cotton; flax; vine; fruit or vegetable crops such as Rosaceae sp. (for instance pip fruit such as apples and pears, but also stone fruit such as apricots, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp.
  • Rosaceae sp. for instance pip fruit such as apples and pears, but also stone fruit such as apricots, almonds and peaches
  • Rosaceae sp. for instance pip fruit such as apples and pears, but also stone fruit such as apricots, almonds and peaches
  • Rubiaceae sp. for instance banana trees and plantins
  • Rubiaceae sp. Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemons oranges and grapefruit); Solanaceae sp. (for instance tomatoes), ⁇ liaceae sp., Asteraceae sp. (for instance lettuces), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp., Papilionaceae sp. (for instance peas), Rosaceae sp. (for instance strawberries); major crops such as Graminae sp.
  • Asteraceae sp. for instance sunflower
  • Cruciferae sp. for instance colza
  • Fabacae sp. for instance peanuts
  • Papilionaceae sp. for instance soybean
  • Solanaceae sp. for instance potatoes
  • Chenopodiaceae sp. for instance beetroots
  • Elaeis sp. for instance oil palm
  • the method of treatment according to the invention can be used in the treatment of genetically modified organisms (GMOs), e.g. plants or seeds.
  • GMOs genetically modified organisms
  • Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
  • the expression "heterologous gene” essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, co suppression technology or RNA interference - RNAi - technology).
  • a heterologous gene that is located in the genome is also called a transgene.
  • a transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
  • the treatment according to the invention may also result in superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the active compounds and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, bigger fruits, larger plant height, greener leaf color, earlier flowering, higher quality and/or a higher nutritional value of the harvested products, higher sugar concentration within the fruits, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected.
  • the active compound combinations according to the invention may also have a strengthening effect in plants. Accordingly, they are also suitable for mobilizing the defense system of the plant against attack by unwanted phytopathogenic fungi and/ or microorganisms and/or viruses. This may, if appropriate, be one of the reasons of the enhanced activity of the combinations according to the invention, for example against fungi.
  • Plant- strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances or combinations of substances which are capable of stimulating the defense system of plants in such a way that, when subsequently inoculated with unwanted phytopathogenic fungi and/ or microorganisms and/or viruses, the treated plants display a substantial degree of resistance to these unwanted phytopathogenic fungi and/ or microorganisms and/or viruses.
  • unwanted phytopathogenic fungi and/ or microorganisms and/or viruses are to be understood as meaning phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can be employed for protecting plants against attack by the abovementioned pathogens within a certain period of time after the treatment.
  • the period of time within which protection is effected generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds.
  • Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means).
  • Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.
  • Plants and plant cultivars which may also be treated according to the invention are those plants which are resistant to one or more abiotic stresses.
  • Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozon exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.
  • Plants and plant cultivars which may also be treated according to the invention are those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation.
  • Yield can furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance.
  • Further yield traits include seed composition, such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability.
  • Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stress factors. Such plants are typically made by crossing an inbred male-sterile parent line (the female parent) with another inbred male-fertile parent line (the male parent). Hybrid seed is typically harvested from the male sterile plants and sold to growers. Male sterile plants can sometimes (e.g. in corn) be produced by detasseling, i.e. the mechanical removal of the male reproductive organs (or males flowers) but, more typically, male sterility is the result of genetic determinants in the plant genome.
  • Male sterile plants can also be obtained by plant biotechnology methods such as genetic engineering.
  • a particularly useful means of obtaining male-sterile plants is described in WO 1989/10396 in which, for example, a ribonuclease such as barnase is selectively expressed in the tapetum cells in the stamens. Fertility can then be restored by expression in the tapetum cells of a ribonuclease inhibitor such as barstar (e.g. WO 1991/002069).
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.
  • Herbicide-tolerant plants are for example glyphosate-tolerant plants, i.e. plants made tolerant to the herbicide glyphosate or salts thereof. Plants can be made tolerant to glyphosate through different means.
  • glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS).
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221 , 370-371 ), the CP4 gene of the bacterium Agrobacterium sp.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate oxido-reductase enzyme as described in US 5,776,760 and US 5,463,175.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate acetyl transferase enzyme as described in for example WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO 2007/024782.
  • Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally- occurring mutations of the above-mentioned genes, as described in for example WO 2001/024615 or WO 2003/013226.
  • herbicide resistant plants are for example plants that are made tolerant to herbicides inhibiting the enzyme glutamine synthase, such as bialaphos, phosphinothricin or glufosinate.
  • Such plants can be obtained by expressing an enzyme detoxifying the herbicide or a mutant glutamine synthase enzyme that is resistant to inhibition.
  • One such efficient detoxifying enzyme is an enzyme encoding a phosphinothricin acetyltransferase (such as the bar or pat protein from Streptomyces species).
  • Plants expressing an exogenous phosphinothricin acetyltransferase are for example described in US 5,561 ,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665.
  • Further herbicide-tolerant plants are also plants that are made tolerant to the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase (HPPD).
  • HPPD hydroxyphenylpyruvatedioxygenase
  • Hydroxyphenylpyruvatedioxygenases are enzymes that catalyze the reaction in which para- hydroxyphenylpyruvate (HPP) is transformed into homogentisate.
  • Plants tolerant to HPPD- inhibitors can be transformed with a gene encoding a naturally-occurring resistant HPPD enzyme, or a gene encoding a mutated HPPD enzyme as described in WO 1996/038567, WO 1999/024585 and WO 1999/024586.
  • Tolerance to HPPD-inhibitors can also be obtained by transforming plants with genes encoding certain enzymes enabling the formation of homogentisate despite the inhibition of the native HPPD enzyme by the HPPD-inhibitor.
  • Tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene encoding an enzyme prephenate dehydrogenase in addition to a gene encoding an HPPD-tolerant enzyme, as described in WO 2004/024928.
  • Still further herbicide resistant plants are plants that are made tolerant to acetolactate synthase (ALS) inhibitors.
  • ALS-inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinone herbicides.
  • ALS enzyme also known as acetohydroxyacid synthase, AHAS
  • AHAS acetohydroxyacid synthase
  • imidazolinone-tolerant plants are also described in for example WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351 , and WO 2006/060634. Further sulfonylurea- and imidazolinone-tolerant plants are also described in for example WO 2007/024782.
  • plants tolerant to imidazolinone and/or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or mutation breeding as described for example for soybeans in US 5,084,082, for rice in WO 1997/41218, for sugar beet in US 5,773,702 and WO 1999/057965 , for lettuce in US 5,198,599, or for sunflower in WO 2001/065922.
  • Plants or plant cultivars which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.
  • An "insect-resistant transgenic plant”, as used herein, includes any plant containing at least one transgene comprising a coding sequence encoding:
  • insecticidal portions thereof e.g., proteins of the Cry protein classes CrylAb, CryiAc, Cry1 F, Cry2Ab, Cry3Aa, or Cry3Bb or insecticidal portions thereof; or 2) a crystal protein from Bacillus thuringiensis or a portion thereof which is insecticidal in the presence of a second other crystal protein from Bacillus thuringiensis or a portion thereof, such as the binary toxin made up of the Cry34 and Cry35 crystal proteins (Moellenbeck et al., Nat.
  • a hybrid insecticidal protein comprising parts of different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1 ) above or a hybrid of the proteins of 2) above, e.g., the Cry1A.1O5 protein produced by corn event MON98034 (WO 2007/027777); or
  • a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin made up of the VIP1A and VIP2A proteins (WO 1994/21795); or
  • a hybrid insecticidal protein comprising parts from different secreted proteins from Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins in 1 ) above or a hybrid of the proteins in 2) above; or
  • 8) a protein of any one of 1 ) to 3) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation (while still encoding an insecticidal protein), such as the VIP3Aa protein in cotton event COT102.
  • an insect-resistant transgenic plant also includes any plant comprising a combination of genes encoding the proteins of any one of the above classes 1 to 8.
  • an insect-resistant plant contains more than one transgene encoding a protein of any one of the above classes 1 to 8, to expand the range of target insect species affected when using different proteins directed at different target insect species, or to delay insect resistance development to the plants by using different proteins insecticidal to the same target insect species but having a different mode of action, such as binding to different receptor binding sites in the insect.
  • Plants or plant cultivars which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance. Particularly useful stress tolerance plants include: a. plants which contain a transgene capable of reducing the expression and/or the activity of poly(ADP-ribose)polymerase (PARP) gene in the plant cells or plants as described in WO 2000/004173 or WO2006/045633 or PCT/EP07/004142.
  • PARP poly(ADP-ribose)polymerase
  • plants which contain a stress tolerance enhancing transgene coding for a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage synthesis pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyl transferase, nicotinamide adenine dinucleotide synthetase or nicotine amide phosphoribosyltransferase as described e.g. in WO2006/032469 or WO 2006/133827 or PCT/EP07/002433.
  • Plants or plant cultivars which may also be treated according to the invention show altered quantity, quality and/or storage-stability of the harvested product and/or altered properties of specific ingredients of the harvested product such as : 1 ) transgenic plants which synthesize a modified starch, which in its physical-chemical characteristics, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the side chain distribution, the viscosity behaviour, the gelling strength, the starch grain size and/or the starch grain morphology, is changed in comparison with the synthesised starch in wild type plant cells or plants, so that this is better suited for special applications.
  • a modified starch which in its physical-chemical characteristics, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the side chain distribution, the viscosity behaviour, the gelling strength, the starch grain size and/or the starch grain morphology, is changed in comparison with
  • Said transgenic plants synthesizing a modified starch are disclosed, for example, in EP 0571427, WO 1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581 , WO 1996/27674, WO 1997/1 1188, WO 1997/26362, WO 1997/32985, WO 1997/42328, WO 1997/44472, WO 1997/45545, WO 1998/27212, WO 1998/40503, WO99/58688, WO 1999/58690, WO 1999/58654, WO 2000/008184, WO 2000/008185, WO 2000/008175, WO 2000/28052,
  • Examples are plants producing polyfructose, especially of the inulin and levan-type, as disclosed in EP 0663956, WO 1996/001904, WO 1996/021023, WO 1998/039460, and WO 1999/024593, plants producing alpha 1 ,4 glucans as disclosed in WO 1995/031553, US 2002/031826, US
  • Plants or plant cultivars which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics.
  • Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics and include: a) Plants, such as cotton plants, containing an altered form of cellulose synthase genes as described in WO 1998/000549 b) Plants, such as cotton plants, containing an altered form of rsw2 or rsw3 homologous nucleic acids as described in WO2004/053219 c) Plants, such as cotton plants, with increased expression of sucrose phosphate synthase as described in WO 2001/017333 d) Plants, such as cotton plants, with increased expression of sucrose synthase as described in WO02/45485 e) Plants, such as cotton plants, wherein the tinning of the plasmodesmatal gating at the basis of the fiber cell is altered, e.
  • Plants such as cotton plants, having fibers with altered reactivity, e.g. through the expression of N-acteylglucosaminetransferase gene including nodC and chitinsynthase genes as described in WO2006/136351
  • Plants or plant cultivars which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics.
  • Such plants can be obtained by genetic transformation or by selection of plants contain a mutation imparting such altered oil characteristics and include: a) Plants, such as oilseed rape plants, producing oil having a high oleic acid content as described e.g.
  • transgenic plants which may be treated according to the invention are plants which comprise one or more genes which encode one or more toxins, such as the following which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), BiteGard® (for example maize), Bt-Xtra® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B®(cotton), NatureGard® (for example maize), Protecta® and NewLeaf® (potato).
  • YIELD GARD® for example maize, cotton, soya beans
  • KnockOut® for example maize
  • BiteGard® for example maize
  • Bt-Xtra® for example maize
  • StarLink® for example maize
  • Bollgard® cotton
  • Nucotn® cotton
  • Nucotn 33B® cotton
  • NatureGard® for example maize
  • herbicide- tolerant plants examples include maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for example maize).
  • Herbicide-resistant plants plants bred in a conventional manner for herbicide tolerance
  • Clearfield® for example maize.
  • transgenic plants which may be treated according to the invention are plants containing transformation events, or combination of transformation events, that are listed for example in the databases from various national or regional regulatory agencies (see for example http://gmoinfo.jrc.it/gmp_browse.aspx and http://www.agbios.com/dbase.php).
  • the composition according to the invention may also be used against fungal diseases liable to grow on or inside timber.
  • the term "timber" means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood.
  • the method for treating timber according to the invention mainly consists in contacting one or more compounds according to the invention or a composition according to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means.
  • Powdery Mildew Diseases such as
  • Blumeria diseases caused for example by Blumeria graminis
  • Podosphaera diseases caused for example by Podosphaera leucotricha
  • Sphaerotheca diseases caused for example by Sphaerotheca fuliginea
  • Uncinula diseases caused for example by Uncinula necator
  • Gymnosporangium diseases caused for example by Gymnosporangium sabinae; Hemileia diseases caused for example by Hemileia vastatrix; Phakopsora diseases caused for example by Phakopsora pachyrhizi and Phakopsora meibomiae;
  • Puccinia diseases caused for example by Puccinia recondita, Puccinia graminis or Puccinia striiformis;
  • Uromyces diseases caused for example by Uromyces append iculatus;
  • Albugo diseases caused for example by Albugo Candida
  • Bremia diseases caused for example by Bremia lactucae
  • Peronospora diseases caused for example by Peronospora pisi and Peronospora brassicae; Phytophthora diseases caused for example by Phytophthora infestans; Plasmopara diseases caused for example by Plasmopara viticola;
  • Pseudoperonospora diseases caused for example by Pseudoperonospora humuli and Pseudo- peronospora cubensis;
  • Leaf spot, Leaf blotch and Leaf Blight Diseases such as
  • Alternaria diseases caused for example by Alternaria solani;
  • Cercospora diseases caused for example by Cercospora beticola
  • Cladiosporium diseases caused for example by Cladiosporium cucumerinum; Cochliobolus diseases caused for example by Cochliobolus sativus (Conidiaform: Drechslera,
  • Colletotrichum diseases caused for example by Colletotrichum lindemuthianum;
  • Cycloconium diseases caused for example by Cycloconium oleaginum
  • Diaporthe diseases caused for example by Diaporthe citri; Elsinoe diseases caused for example by Elsinoe fawcettii;
  • Gloeosporium diseases caused for example by Gloeosporium laeticolor
  • Glomerella diseases caused for example by Glomerella cingulata caused for example by Glomerella cingulata
  • Guignardia diseases caused for example by Guignardia bidwellii;
  • Leptosphaeria diseases caused for example by Leptosphaeria maculans and Leptosphaeria nodorum;
  • Magnaporthe diseases caused for example by Magnaporthe grisea
  • Mycosphaerella diseases caused for example by Mycosphaerella graminicola, Mycosphaerella arachidicola and Mycosphaerella fijiensis;
  • Phaeosphaeria diseases caused for example by Phaeosphaeria nodorum
  • Pyrenophora diseases caused for example by Pyrenophora teres or Pyrenophora tritici repentis
  • Ramularia- diseases caused for example by Ramularia collo-cygni or Ramularia areola;
  • Rhynchosporium diseases caused for example by Rhynchosporium secalis
  • Septoria diseases caused for example by Septoria apii and Septoria lycopersici
  • Thyphula incarnata a diseases caused for example by Thyphula incarnata
  • Venturia diseases caused for example by Venturia inaequalis
  • Root-, Sheath and Stem Diseases such as
  • Corticium diseases caused for example by Corticium graminearum Fusarium diseases caused for example by Fusarium oxysporum; Gaeumannomyces diseases caused for example by Gaeumannomyces graminis; Rhizoctonia diseases caused for example by Rhizoctonia solani; Sarocladium diseases caused for example by Sarocladium oryzae; Sclerotium diseases caused for example by Sclerotium oryzae; Tapesia diseases caused for example by Tapesia acuformis; Thielaviopsis diseases caused for example by Thielaviopsis basicola;
  • Ear and Panicle Diseases including Maize cob such as Alternaria diseases caused for example by Alternaria spp.; Aspergillus diseases caused for example by Aspergillus flavus; Cladosporium diseases caused for example by Cladiosporium cladosporioides; Claviceps diseases caused for example by Claviceps purpurea; Fusarium diseases caused for example by Fusarium culmorum; Gibberella diseases caused for example by Gibberella zeae; Monographella diseases caused for example by Monographella nivalis;
  • Sphacelotheca diseases caused for example by Sphacelotheca reiliana; Tilletia diseases caused for example by Tilletia caries; Urocystis diseases caused for example by Urocystis occulta; Ustilago diseases caused for example by Ustilago nuda;
  • Aspergillus diseases caused for example by Aspergillus flavus
  • Botrytis diseases caused for example by Botrytis cinerea
  • Penicillium diseases caused for example by Penicillium expansum and Penicillium purpurogenum
  • Rhizopus diseases caused by example by Rhizopus stolonifer Sclerotinia diseases caused for example by Sclerotinia sclerotiorum; Verticillium diseases caused for example by Verticillium alboatrum;
  • Cochliobolus diseases caused for example by Cochliobolus sativus;
  • Colletotrichum diseases caused for example by Colletotrichum coccodes; Fusarium diseases caused for example by Fusarium culmorum;
  • Macrophomina diseases caused for example by Macrophomina phaseolina
  • Microdochium diseases caused for example by Microdochium nivale
  • Phomopsis diseases caused for example by Phomopsis sojae
  • Pyrenophora diseases caused for example by Pyrenophora graminea; Pyricularia diseases caused for example by Pyricularia oryzae;
  • Rhizoctonia diseases caused for example by Rhizoctonia solani;
  • Rhizopus diseases caused for example by Rhizopus oryzae
  • Sclerotium diseases caused for example by Sclerotium rolfsii; Septoria diseases caused for example by Septoria nodorum;
  • Typhula diseases caused for example by Typhula incarnata
  • Verticillium diseases caused for example by Verticillium dahliae
  • Nectria diseases caused for example by Nectria galligena
  • Leaf Blister or Leaf Curl Diseases including deformation of blooms and fruits such as Exobasidium diseases caused for example by Exobasidium vexans.
  • Decline Diseases of Wooden Plants such as Esca disease caused for example by Phaeomoniella clamydospora, Phaeoacremonium aleophilum and Fomitiporia mediterranea;
  • Ganoderma diseases caused for example by Ganoderma boninense
  • Rigidoporus diseases caused for example by Rigidoporus lignosus
  • Botrytis diseases caused for example by Botrytis cinerea
  • Rhizoctonia diseases caused for example by Rhizoctonia solani
  • Helminthosporium diseases caused for example by Helminthosporium solani;
  • Plasmodiophora diseases cause for example by Plamodiophora brassicae.
  • Bacterial Organisms such as Xanthomonas species for example Xanthomonas campestris pv. oryzae; Pseudomonas species for example Pseudomonas syringae pv. lachrymans; Erwinia species for example Erwinia amylovora.
  • the damaging insects of crops which can be controlled at any development stage by using the pesticide composition according to the invention include:
  • Thysanoptera for example Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis
  • pests from the order of Heteroptera for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp;
  • pests from the order of Homoptera for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli,
  • Rhopalosiphum padi Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp;
  • pests from the order of Lepidoptera for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella,
  • Plutella xylostella Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella,
  • Hofmannophila pseudospretella Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae;
  • pests from the order of Coleoptera for example Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus,
  • oryzaephilus surinamensis Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp.,
  • Niptus hololeucus Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitial is, Costelytra zealandica, Lissorhoptrus oryzophilus;
  • pests from the order of Siphonaptera for example Xenopsylla cheopis, Ceratophyllus spp.;
  • pests from the class of Arachnida for example Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp. ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis,
  • the present invention provides a product comprising compounds (A), (B), (C) and (D) as herein defined, as a combined preparation for simultaneous, separate or sequential use in controlling the phytopathogenic fungi or damaging insects of plants, crops or seeds at a site.
  • the pesticide composition according to the invention can be prepared immediately before use by using a kit-of-parts for controlling, curatively or preventively, the phytopathogenic fungi of crops, such a kit-of-parts may comprise at least one or several compounds (A), (B), (C) and (D) intended to be combined or used simultaneously, separately or sequentially in controlling the phytopathogenic fungi of crops at a site.
  • ingredients which comprise in particular the active agents (A), (B), (C) and (D) and which are packaged separately, are provided in the form of a powder or in the form of a liquid which is concentrated to a greater or lesser degree.
  • the user simply has to mix in the prescribed doses and to add the quantities of liquid, for example of water, necessary to obtain a formulation which is ready to use and which can be applied to the crops.
  • the good fungicidal activity of the active compound combinations according to the invention is evident from the example below. While the individual active compounds exhibit weaknesses with regard to the fungicidal activity, the combinations have an activity which exceeds a simple addition of activities.
  • a synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
  • X is the efficacy, when applying the active compound A at a rate of application of active compound of m ppm,
  • Y is the efficacy, when applying the active compound B at a rate of application of active compound of n ppm,
  • E is the expected efficacy, when applying the active compounds A and B at rates of application of active compound of m and n ppm,
  • the degree of efficacy, expressed in % is denoted. 0% means an efficacy which corresponds to that of the control while an efficacy of 100% means that no disease is observed.
  • the activity of the combination is superadditive, i.e. a synergistic effect exists.
  • the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the abovementioned formula.
  • Example A Phytophthora test (tomatoes) / protective
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the test is evaluated 3 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.
  • Table 1 Phytophthora test (tomatoes) / protective
  • Example B Sphaerotheca test (cucumbers) / protective
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the test is performed under greenhouse conditions.
  • Perlite was incubated with mycelium fragments of Pythium ultimum. 1 ml of infected perlite was scattered between the treated cotton seeds. Seeds were then covered by light expanded clay aggregate. Pots were incubated in the greenhouse 7 days at 2O 0 C and 80% relative humidity.

Abstract

The present invention relates to a pesticide composition intended for protecting plants, crops or seeds against fungal diseases or insect damages, and the corresponding methods of protection by application of the said composition. More precisely, the subject of the present invention is a pesticide composition based on a tetrazolyloximederivative and a fungicide or an insecticide active substance or compound.

Description

PESTICIDE COMPOSITION COMPRISING A TETRAZOLYLOXIME DERIVATIVE AND A FUNGICIDE OR AN INSECTICIDE ACTIVE SUBSTANCE
DESCRIPTION
The present invention relates to a pesticide composition intended for protecting plants, crops or seeds against fungal diseases or insect damages, and the corresponding methods of protection by application of the said composition. More precisely, the subject of the present invention is a pesticide composition based on a tetrazolyloxime derivative and a fungicide or an insecticide active substance or compound.
As regards pesticide activity, in particular for the protection of crops, one of the problems at the heart of the research studies carried out in this technical field is the improvement of performances, in particular in terms of biological activity and in particular in terms of maintaining such an activity over time.
The present invention provides a pesticide composition which can be used, in particular by the farmer, for controlling the pest infesting crops and in particular for controlling insects or diseases.
The pesticide compounds useful for the protection of plants must be endowed with an ecotoxicity which is reduced to the minimum. As far as possible, they should not be dangerous or toxic to the operator during use. The economic factor should of course not be overlooked in the search for novel pesticide agents.
The present invention advantageously provides a pesticide composition which is completely high-performing in particular as regards its efficacy against pests and the perennially of this efficacy so as to be able to reduce the doses of chemical products spread in the environment for combating pest damages or attacks of plants or crops.
The invention provides a pesticide composition capable to be more active and active for longer, and which therefore has a lower dose, but which is also less toxic, in particular in the treatment of plants and particularly the foliar and seed treatments of fungal diseases or the control of insects, for example, of cereals, cotton, peanut, bean, beet, canola, Solanaceae, grapevine, vegetables, lucerne, soybean, market garden crops, turf, wood or horticultural plants. The composition according to the invention allows controlling a broad variety of insects or fungi. For example, the pesticide composition according to the invention exhibits an improved efficacy against fungus like Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Basidiomycetes, Deuteromycetes and Ascomycetes. All these objectives or advantages, among others, were achieved by finding a pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide compound. Such a composition surprisingly and unexpectedly allows a very high and perennial anti-fungal or insecticide efficacy against a broad spectrum of insects or fungi and in particular against those responsible for diseases or damages of crops. Other insect pests or diseases of crops can be controlled with the pesticide composition according to the invention. The pesticide composition according to the invention may also be used for the treatment of bacterial or virus diseases. Insects or nematodes that can be controlled with the pesticide composition according to the invention include a broad variety of these damaging organisms.
In patent applications US-2005/0070439, WO 2009/020191 and PCT/EP2009/058427, there are disclosed certain tetrazolyloxime derivatives, and their preparation from commercially available materials. The possibility to mix said compounds with other chemicals is generally mentioned. However, there is no specific disclosure in these documents of any combination comprising said tetrazolyloxime derivatives with a fungicide or an insecticide compound.
In a main aspect, the present invention provides a composition comprising: A) a tetrazolyloxime derivative of formula (I)
Figure imgf000003_0001
(I) wherein
• R1 represents a hydrogen atom, a halogen atom, a substituted or non-substituted Ci-C6- alkyl, a substituted or non-substituted d-C6-alkoxy, nitro, cyano, a substituted or non- substituted d-C6-aryl or a substituted or non-substituted d-C6-alkylsulphonyl;
• q represents 0,1 , 2, 3, 4 or 5;
• A represents a tetrazoyl group of formula (A1) or (A2):
Figure imgf000004_0001
(A1) (A2) wherein Y represents an d-C6-alkyl group ; and D represents a pyridyl group of formula (D1) or a thiazolyl group of formula (D2) ;
Figure imgf000004_0002
(D1) (D2) wherein R2 and R3 independently represent a hydrogen atom, a halogen atom, a substituted or non-substituted Ci-C8-alkyl, nitro, cyano, a hydroxy group, a mercapto group, formyl, hydroxycarbonyl, a substituted or non-substituted amino, a substituted or non-substituted C2-C8-alkenyl, a substituted or non-substituted C2-C8-alkynyl, a substituted or non-substituted aryl, a substituted or non-substituted heterocyclyl, ORa , S(O)rRa, C0Ra or C02Ra; wherein Ra represents a substituted or non-substituted C1-C8- alkyl, a substituted or non-substituted amino, a substituted or non-substituted C3-C8- cycloalkyl, a substituted or non-substituted C2-C8-alkenyl, a substituted or non- substituted C2-C8-alkynyl, a substituted or non-substituted aryl; wherein r represents 0, 1 or 2; n represents 0, 1 , 2 or 3;
Provided that when n represents 0 or when R3 represents a hydrogen atom, Z represents Q1CONH- , wherein Q1 represents a substituted or non-substituted Ci-C8- haloalkyl comprising between one and 9 halogen atoms, a substituted or non- substituted C2-C8-haloalkenyl comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkynyl, a substituted or non-substituted C2-C8- haloalkynyl comprising between one and 9 halogen atoms, a substituted or non- substituted Ci-C8-haloalkoxy comprising between one and 9 halogen atoms, , a substituted or non-substituted C2-C8-alkenyloxy, a substituted or non-substituted C2-C8- haloalkenyloxy comprising between one and 9 halogen atoms, a substituted or non- substituted C2-C8-alkynyloxy, a substituted or non-substituted C2-C8-haloalkynyloxy comprising between one and 9 halogen atoms, a Ci-C8-alkoxy substituted with a Ci-C8- alkoxycarbonylamino, a Ci-C8-alkoxy substituted with a C3-C8-cycloalkyl, a branched Ci-C8-alkyl substituted with an aryl, a Ci-C8-alkoxy substituted with an aryl, a Ci-C8- alkoxy substituted with a substituted or unsubstituted heterocyclyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkoxy, a Ci-C8-alkoxy substituted with a substituted or unsubstituted aryloxy, a Ci-C8-alkoxy substituted with a substituted or unsubstituted aralkyloxy, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylthio, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-arylthio, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylsulphinyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted arylsulphinyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted d-C8-alkylsulphony, a d-C8-alkoxy substituted with a substituted or unsubstituted arylsulphonyl, d-C8-alkoxy substituted with a substituted or unsubstituted
C-rCs-alkylannino, C-ι-C8-alkoxy substituted with a substituted or unsubstituted aralkylamino, an aryloxy, d-C8-alkyl substituted with a carboxyl residue, d-C8-alkyl substituted with a substituted or unsubstituted aralkylamino, d-C8-alkyl substituted with a substituted or unsubstituted aryloxy, d-C8-alkyl substituted with an acyl group, C1-C8- alkyl substituted with a substituted or unsubstituted heterocyclyl group;
Provided that when n represents 1 and R2 represents a halogen atom, Z represents a hydrogen atom, an amino or Q2CONH-, wherein Q2 represents a hydrogen atom, a substituted or non-substituted Ci-C8-haloalkyl comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkenyl, a substituted or non-substituted C2-C8-haloalkenyl comprising between one and 9 halogen atoms, a substituted or non- substituted C2-C8-alkynyl, a substituted or non-substituted C2-C8-haloalkynyl comprising between one and 9 halogen atoms, a substituted or non-substituted Ci-C8-alkoxy, a substituted or non-substituted Ci-C8-haloalkoxy comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkenyloxy, a substituted or non- substituted C2-C8-haloalkenyloxy comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkynyloxy, a substituted or non-substituted C2-C8- haloalkynyloxy comprising between one and 9 halogen atoms, a substituted or unsubstituted C3-C8-cycloalkyl, a substituted or unsubstituted C3-C8-cycloalkoxy, a substituted or non-substituted d-C8-alkylamino, a d-C8-alkoxy substituted or non- substituted amino, a d-C8-alkoxy substituted with a C3-C8-cycloalkyl, a substituted or unsubstituted aralkyloxy, a d-C8-alkoxy substituted with a substituted or unsubstituted heterocyclyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8- alkoxy, a Ci-C8-alkoxy substituted with a substituted or unsubstituted aryloxy, a Ci-C8- alkoxy substituted with a substituted or unsubstituted aralkyloxy, C2-C8-alkynyloxy substituted with a substituted or unsubstituted aryl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylthio, a CrC8-alkoxy substituted with a substituted or unsubstituted Ci-C8-arylthio, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylsulphinyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted arylsulphinyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylsulphony, a Ci-C8-alkoxy substituted with a substituted or unsubstituted arylsulphonyl, an aryloxy, Ci-C8-alkyl substituted with a carboxyl residue, Ci-C8-alkyl substituted with a substituted or unsubstituted amino, Ci-C8-alkyl substituted with a substituted or unsubstituted aryloxy, a Ci-C8-alkyl substituted with a substituted or unsubstituted d-C8-alkylthio, a d-C8-alkyl substituted with a substituted or unsubstituted d-C8-alkoxy, d-C8-alkyl substituted with an acyl group, d-C8-alkyl substituted with a substituted or unsubstituted heterocyclyl group; Provided that when R3 represents a halogen atom, Z represents a hydrogen atom, an amino or Q1CONH-, Q1 being herein-defined;
Provided that when n represents 2 or 3 and when R2 or R3 independently represents a hydroxy group, a mercapto group, a non-substituted d-C8-alkyl, nitro, cyano, formyl, hydroxycarbonyl, a substituted or non-substituted amino, a substituted or non- substituted C2-C8-alkenyl, a substituted or non-substituted C2-C8-alkynyl, a substituted or non-substituted aryl, a substituted or non-substituted heterocyclyl, ORa , S(O)rRa, C0Ra or CO2R3 , Ra being herein-defined or when n represents 3 and when R2 represents a halogen atom, Z represents a hydrogen atom, an amino or Q3CONH- , wherein Q3 represents a hydrogen atom, a substituted or non-substituted Ci-C8-alkyl, a substituted or non-substituted Ci-C8-haloalkyl comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkenyl, a substituted or non-substituted C2-C8-haloalkenyl comprising between one and 9 halogen atoms, a substituted or non- substituted C2-C8-alkynyl, a substituted or non-substituted C2-C8-haloalkynyl comprising between one and 9 halogen atoms, a substituted or non-substituted d-C8-alkoxy, a substituted or non-substituted d-C8-haloalkoxy comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkenyloxy, a substituted or non- substituted C2-C8-haloalkenyloxy comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkynyloxy, a substituted or non-substituted C2-C8- haloalkynyloxy comprising between one and 9 halogen atoms, a substituted or unsubstituted C3-C8-cycloalkyl, a substituted or unsubstituted C3-C8-cycloalkoxy, a substituted or non-substituted Ci-C8-alkylamino, a Ci-C8-alkoxy substituted or non- substituted amino, a Ci-C8-alkoxy substituted with a C3-C8-cycloalkyl, a substituted or unsubstituted aralkyloxy, a Ci-C8-alkoxy substituted with a substituted or unsubstituted heterocyclyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8- alkoxy, a Ci-C8-alkoxy substituted with a substituted or unsubstituted aryloxy, a Ci-C8- alkoxy substituted with a substituted or unsubstituted aralkyloxy, C2-C8-alkynyloxy substituted with a substituted or unsubstituted aryl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylthio, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-arylthio, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylsulphinyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted arylsulphinyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylsulphonyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted arylsulphonyl, an aryloxy, Ci-C8-alkyl substituted with a carboxyl residue,
Ci-C8-alkyl substituted with a substituted or unsubstituted amino, Ci-C8-alkyl substituted with a substituted or unsubstituted aryloxy, a Ci-C8-alkyl substituted with a substituted or unsubstituted Ci-C8-alkylthio, a Ci-C8-alkyl substituted with a substituted or unsubstituted Ci-C8-alkoxy, Ci-C8-alkyl substituted with an acyl group, Ci-C8-alkyl substituted with a substituted or unsubstituted heterocyclyl group;
as well as salts, N-oxides, metallic complexes and metalloidic complexes thereof or (E) and (Z) isomers and mixtures thereof
and
B) a fungicide compound in an A/B weight ratio ranging from 0.001/1 to 1/1 ,000.
Any of the compounds according to the invention can exist as one or more stereoisomers depending on the number of stereogenic units (as defined by the IUPAC rules) in the compound. The invention thus relates equally to all the stereoisomers, and to the mixtures of all the possible stereoisomers, in all proportions. The stereoisomers can be separated according to the methods which are known per se by the man ordinary skilled in the art. Notably, the stereostructure of the oxime moiety present in the heterocyclyloxime derivative of formula (I) includes (E) or (Z) isomer, and these stereoisomers form part of the present invention.
According to the invention, the following generic terms are generally used with the following meanings: • halogen means fluorine, chlorine, bromine or iodine ;
• heteroatom can be nitrogen, oxygen or sulphur ;
• unless indicated otherwise, a group or a substituent that is substituted according to the invention can be substituted by one or more of the following groups or atoms: a halogen atom, a nitro group, a hydroxy group, a cyano group, an isocyano group, an isocyanate group, an thiocyanate group, an amino group, a sulphenyl group, a formyl group, a formyloxy group, a carbamoyl group, a Ci-C8-alkyl, a Ci-C8- halogenoalkyl having 1 to 5 halogen atoms, a C2-C8-alkenyl, a C2-C8-alkynyl, a C2-C8- alkenyloxy, a Ci-C8-alkylamino, a di-Ci-C8-alkylamino, a phenylamino, a benzylamino, a phenethylamino, a Ci-C8-alkoxy, a Ci-C8-halogenoalkoxy having 1 to 5 halogen atoms, a Ci-C8-alkylsulphenyl, a Ci-C8-alkylcarbonyl, a Ci-C8-alkylthiocarbonyl, a Ci-C8- alkylcarbamoyl, a di-Ci-C8-alkylcarbamoyl, a Ci-C8-alkoxycarbonyl, a Ci-C8- alkylcarbonyloxy, , a Ci-Cs-alkylcarbonylamino, Ci-C8-alkoxycarbonylamino, a Ci-C8- alkylsulphenyl, a Ci-C8-alkylsulphonyl, a C2-C8-alkenylsulphonyl, a C3-C8-alkynyl- sulphonyl, arylsulphonyl, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclylsulphonyl, aryl-[Ci-C8]-alkylsulphonyl, a Ci-C8-alkylsulfamoyl, a Ci-C8- halogenoalkyl sulfamoyl having 1 to 5 halogen atoms, a N-di(Ci-C8-alkyl)sulfamoyl, a N- di(Ci-C8-halogenoalkyl) sulfamoyl having 1 to 5 halogen atoms, arylsulfamoyl, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclylsulfamoyl aryl-[Ci-C8]-alkyl, , saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl-[Ci-C8]-alkyl comprising up to 4 heteroatoms selected in the list consisting of N, O, S, aryl-[Ci-C8]-alkoxy, aryloxy, aryl, (Ci-C8-alkylimino)-Ci-C8-alkyl, saturated or unsaturated A-, 5-, 6- or 7- membered heterocyclyl, aryl-[Ci-C8]-alkylthio, arylthio, saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclylthio; • the term "aryl" means phenyl or naphthyl
• the tern "heterocyclyl" means saturated or unsaturated A-, 5-, 6- or 7-membered heterocyclyl.
In a further aspect, the present invention provides a composition comprising:
A) a tetrazolyloxime derivative of formula (I) wherein formula (I) is as herein-defined ;
B) a fungicide compound and
C) a second further fungicide compound in an A/B/C weight ratio ranging from 0.001/0.001/1 to 1/1 ,000/1 ,000. Still in a further aspect, the present invention provides a composition comprising:
A) a tetrazolyloxime derivative of formula (I) wherein formula (I) is as herein-defined ;
B) a fungicide compound and
D) an insecticide compound in an A/B/D weight ratio ranging from 0.001/0.001/1 to 1/1 ,000/1 ,000.
Still in a further aspect, the present invention provides a composition comprising:
A) a tetrazolyloxime derivative of formula (I) wherein formula (I) is as herein-defined ; and D) an insecticide compound in an A/D weight ratio ranging from 1/1 ,000 to 1 ,000/1.
Still in a further aspect, the present invention provides a composition comprising:
A) a tetrazolyloxime derivative of formula (I) wherein formula (I) is as herein-defined ;
B) a fungicide compound ; C) a second further fungicide compound and
D) an insecticide compound in an A/B/C/D weight ratio ranging from 0.001/0.001/0.001/1 to 1/1 ,000/1 ,000/1 ,000.
In the tetrazolyloxime derivative of formula (I), the substitution position of R1 is not specifically limited and R1 represents preferentially a hydrogen atom, a halogen atom, a substituted or non- substituted Ci-C6-alkyl, a substituted or non-substituted d-C6-alkoxy.
The alkyl group represented for R1 is preferably an alkyl group having 1 to 4 carbon atoms and specific examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Among these alkyl groups, a methyl group or a tert-butyl group is particularly preferred.
The d-C6-alkoxy group for R1 is preferably alkoxy group having 1 to 3 carbon atoms and specific examples thereof include a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group. Among these alkoxy groups, a methoxy group or an ethoxy group is particularly preferred.
R1 represents more preferentially a hydrogen atom or a halogen atom.
In the tetrazoyl group of formula (A1) or (A2), Y represents an alkyl group. Among these alkyl groups, an alkyl group having 1 to 3 carbon atoms such as a methyl group, an ethyl group, a n- propyl group or an isopropyl group is preferable. Among these alkyl groups, a methyl group is particularly preferred.
R2 and R3 independently represent preferentially a hydrogen atom or a halogen atom.
For the tetrazolyloxime derivative of formula (I), preference is further given to but-3-yn-1-yl {6- [({[(Z)-(1-methyl-1 H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (compound A).
Figure imgf000010_0001
Compound A
The stereostructure of the oxime moiety present in the tetrazolyloxime derivative of formula (I) includes (E) or (Z) isomer, and these stereoisomers form part of the present invention. The synthesized product is generally obtained in the form of the (Z) isomer or a mixture of (E) and (Z) isomers, each of which can be isolated by separation or purification. In the tetrazolyloxime derivative of formula (I), the (Z) isomer is particularly superior to the (E) isomer in plant disease controlling activity. However, both the (E) isomer and the (Z) isomer generally exist in a fixed ratio in the form of a mixture since the (Z) isomer is generally converted into the (E) isomer by light in a natural environment. The stable ratios of the (E) and (Z) isomers vary according to the type of compound.
For the different aspects of the composition according to the invention, fungicide compounds B and C can be independently selected in the list L1 consisting of:
(1 ) Inhibitors of the ergosterol biosynthesis, for example (1.1 ) aldimorph (1704-28-5), (1.2) azaconazole (60207-31-0), (1.3) bitertanol (55179-31-2), (1.4) bromuconazole (116255-48-2), (1.5) cyproconazole (113096-99-4), (1.6) diclobutrazole (75736-33-3), (1.7) difenoconazole (119446-68-3), (1.8) diniconazole (83657-24-3), (1.9) diniconazole-M (83657-18-5), (1.10) dodemorph (1593-77-7), (1.1 1 ) dodemorph acetate (31717-87-0), (1.12) epoxiconazole (106325-08-0), (1.13) etaconazole (60207-93-4), (1.14) fenarimol (60168-88-9), (1.15) fenbuconazole (114369-43-6), (1.16) fenhexamid (126833-17-8), (1.17) fenpropidin (67306-00- 7), (1.18) fenpropimorph (67306-03-0), (1.19) fluquinconazole (136426-54-5), (1.20) flurprimidol (56425-91-3), (1.21 ) flusilazole (85509-19-9), (1.22) flutriafol (76674-21-0), (1.23) furconazole (112839-33-5), (1.24) furconazole-cis (112839-32-4), (1.25) hexaconazole (79983-71-4), (1.26) imazalil (60534-80-7), (1.27) imazalil sulfate (58594-72-2), (1.28) imibenconazole (86598-92-7), (1.29) ipconazole (125225-28-7), (1.30) metconazole (125116-23-6), (1.31 ) myclobutanil (88671-89-0), (1.32) naftifine (65472-88-0), (1.33) nuarimol (63284-71-9), (1.34) oxpoconazole (174212-12-5), (1.35) paclobutrazol (76738-62-0), (1.36) pefurazoate (101903-30-4), (1.37) penconazole (66246-88-6), (1.38) piperalin (3478-94-2), (1.39) prochloraz (67747-09-5), (1.40) propiconazole (60207-90-1 ), (1.41 ) prothioconazole (178928-70-6), (1.42) pyributicarb (88678- 67-5), (1.43) pyrifenox (88283-41-4), (1.44) quinconazole (103970-75-8), (1.45) simeconazole (149508-90-7), (1.46) spiroxamine (118134-30-8), (1.47) tebuconazole (107534-96-3), (1.48) terbinafine (91 161-71-6), (1.49) tetraconazole (112281-77-3), (1.50) triadimefon (43121-43-3), (1.51 ) triadimenol (89482-17-7), (1.52) tridemorph (81412-43-3), (1.53) triflumizole (68694-11- 1 ), (1.54) triforine (26644-46-2), (1.55) triticonazole (131983-72-7), (1.56) uniconazole (83657- 22-1 ), (1.57) uniconazole-p (100761-65-7), (1.58) viniconazole (77174-66-4), (1.59) voriconazole (137234-62-9), (1.60) i-^-chlorophenyl^-O H-i ^^-triazol-i-yOcycloheptanol (129586-32-9), (1.61 ) methyl 1-(2,2-dimethyl-2,3-dihydro-1 H-inden-1-yl)-1 H-imidazole-5- carboxylate (11 1323-95-0), (1.62) N'-{5-(difluoromethyl)-2-methyl-4-[3-
(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-nnethylinnidofornnannide, (1.63) N-ethyl-N-methyl-N'-{2- methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide and (1.64) O-{1- [(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl} I H-imidazole-1-carbothioate (11 1226-71-2).
(2) inhibitors of the respiratory chain at complex I or II, for example (2.1 ) bixafen (581809-46- 03), (2.2) boscalid (188425-85-6), (2.3) carboxin (5234-68-4), (2.4) diflumetorim (130339-07-0), (2.5) fenfuram (24691-80-3), (2.6) fluopyram (658066-35-4), (2.7) flutolanil (66332-96-5), (2.8) furametpyr (123572-88-3), (2.9) furmecyclox (60568-05-0), (2.10) isopyrazam (mixture of syn- epimeric racemate 1 RS,4SR,9RS and anti-epimeric racemate 1 RS,4SR,9SR) (881685-58-1 ), (2.1 1 ) isopyrazam (anti-epimeric racemate 1 RS,4SR,9SR), (2.12) isopyrazam (anti-epimeric enantiomer 1 R,4S,9S), (2.13) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (2.14) isopyrazam (syn epimeric racemate 1 RS, 4SR, 9RS), (2.15) isopyrazam (syn-epimeric enantiomer 1 R,4S,9R), (2.16) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.17) mepronil (55814-41-0), (2.18) oxycarboxin (5259-88-1 ), (2.19) penflufen (494793-67-8), (2.20) penthiopyrad (183675-82-3), (2.21 ) sedaxane (874967-67-6), (2.22) thifluzamide (130000-40-7), (2.23) 1-methyl-N-[2-(1 ,1 ,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1 H-pyrazole-4- carboxamide, (2.24) 3-(difluoromethyl)-1-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-1 H-pyrazole-4- carboxamide, (2.25) 3-(difluoromethyl)-1-methyl-N-[2-(1 ,1 ,2,2-tetrafluoroethoxy)phenyl]-1 H- pyrazole-4-carboxamide, (2.26) 3-(difluoromethyl)-N-[4-fluoro-2-(1 ,1 ,2,3,3,3- hexafluoropropoxy)phenyl]-1-nnethyl-1 H-pyrazole-4-carboxannide and salts thereof.
(3) inhibitors of the respiratory chain at complex III, for example (3.1 ) amisulbrom (348635-87- 0), (3.2) azoxystrobin (131860-33-8), (3.3) cyazofamid (120116-88-3), (3.4) dimoxystrobin (141600-52-4), (3.5) enestroburin (238410-1 1-2) (known from WO 2004/058723), (3.6) famoxadone (131807-57-3) (known from WO 2004/058723), (3.7) fenamidone (161326-34-7) (known from WO 2004/058723), (3.8) fluoxastrobin (361377-29-9) (known from WO 2004/058723), (3.9) kresoxim-methyl (143390-89-0) (known from WO 2004/058723), (3.10) metominostrobin (133408-50-1 ) (known from WO 2004/058723), (3.11 ) orysastrobin (189892- 69-1 ) (known from WO 2004/058723), (3.12) picoxystrobin (117428-22-5) (known from WO 2004/058723), (3.13) pyraclostrobin (175013-18-0) (known from WO 2004/058723), (3.14) pyrametostrobin (915410-70-7) (known from WO 2004/058723), (3.15) pyraoxystrobin (862588- 11-2) (known from WO 2004/058723), (3.16) pyribencarb (799247-52-2) (known from WO 2004/058723), (3.17) trifloxystrobin (141517-21-7) (known from WO 2004/058723), (3.18) (2E)- 2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N- methylethanamide (known from WO 2004/058723), (3.19) (2E)-2-(methoxyimino)-N-methyl-2- (2-{[({(1 E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide (known from WO 2004/058723) and salts thereof., (3.20) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1- [3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide (158169-73-4), (3.21 ) (2E)-2- {2-[({[(1 E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}- 2-(methoxyimino)-N-methylethanamide (326896-28-0), (3.22) (2E)-2-{2-[({[(2E,3E)-4-(2,6- dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N- methylethanamide, (3.23) 2-chloro-N-(1 ,1 ,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)pyridine-3- carboxamide (119899-14-8), (3.24) 5-methoxy-2-methyl-4-(2-{[({(1 E)-1-[3- (trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1 ,2,4-triazol-3-one, (3.25) methyl 2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3- methoxyacrylate (149601-03-6), (3.26) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2- hydroxybenzamide (226551-21-9) and salts thereof.
(4) Inhibitors of the mitosis and cell division, for example (4.1 ) benomyl (17804-35-2), (4.2) carbendazim (10605-21-7), (4.3) chlorfenazole (3574-96-7), (4.4) diethofencarb (87130-20-9),
(4.5) ethaboxam (162650-77-3), (4.6) fluopicolide (239110-15-7), (4.7) fuberidazole (3878-19- 1 ), (4.8) pencycuron (66063-05-6), (4.9) thiabendazole (148-79-8), (4.10) thiophanate-methyl (23564-05-8), (4.1 1 ) thiophanate (23564-06-9), (4.12) zoxamide (156052-68-5) and (4.13) 5- chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1 ,2,4]triazolo[1 ,5-a]pyrimidine
(214706-53-3).
(5) Compounds capable to have a multisite action, like for example (5.1 ) bordeaux mixture (8011-63-0), (5.2) captafol (2425-06-1 ), (5.3) captan (133-06-2) (known from WO 02/12172), (5.4) chlorothalonil (1897-45-6), (5.5) copper hydroxide (20427-59-2), (5.6) copper naphthenate (1338-02-9), (5.7) copper oxide (1317-39-1 ), (5.8) copper oxychloride (1332-40-7), (5.9) copper(2+) sulfate (7758-98-7), (5.10) dichlofluanid (1085-98-9), (5.1 1 ) dithianon (3347-22-6), (5.12) dodine (2439-10-3), (5.13) dodine free base, (5.14) ferbam (14484-64-1 ), (5.15) fluorofolpet (719-96-0), (5.16) folpet (133-07-3), (5.17) guazatine (108173-90-6), (5.18) guazatine acetate, (5.19) iminoctadine (13516-27-3), (5.20) iminoctadine albesilate (169202-06- 6), (5.21 ) iminoctadine triacetate (57520-17-9), (5.22) mancopper (53988-93-5), (5.23) mancozeb (2234562), (5.24) maneb (12427-38-2), (5.25) metiram (9006-42-2), (5.26) metiram zinc (9006-42-2), (5.27) oxine-copper (10380-28-6), (5.28) propamidine (104-32-5), (5.29) propineb (12071-83-9), (5.30) sulphur and sulphur preparations including calcium polysulphide (7704-34-9), (5.31 ) thiram (137-26-8), (5.32) tolylfluanid (731-27-1 ), (5.33) zineb (12122-67-7), (5.34) ziram (137-30-4) and salts thereof.
(6) Compounds capable to induce a host defence, like for example (6.1 ) acibenzolar-S-methyl (135158-54-2), (6.2) isotianil (224049-04-1 ), (6.3) probenazole (27605-76-1 ) and (6.4) tiadinil (223580-51-6). (7) Inhibitors of the amino acid and/or protein biosynthesis, for example (7.1 ) andoprim (23951- 85-1 ), (7.2) blasticidin-S (2079-00-7), (7.3) cyprodinil (121552-61-2), (7.4) kasugamycin (6980- 18-3), (7.5) kasugamycin hydrochloride hydrate (19408-46-9), (7.6) mepanipyrim (110235-47-7) and (7.7) pyrimethanil (53112-28-0).
(8) Inhibitors of the ATP production, for example (8.1 ) fentin acetate (900-95-8), (8.2) fentin chloride (639-58-7), (8.3) fentin hydroxide (76-87-9), (8.4) and silthiofam (175217-20-6).
(9) Inhibitors of the cell wall synthesis, for example (9.1 ) benthiavalicarb (177406-68-7), (9.2) dimethomorph (110488-70-5), (9.3) flumorph (211867-47-9), (9.4) iprovalicarb (140923-17-7), (9.5) mandipropamid (374726-62-2), (9.6) polyoxins (11 113-80-7), (9.7) polyoxorim (22976-86- 9), (9.8) validamycin A (37248-47-8) and (9.9) valifenalate (283159-94-4; 283159-90-0). (10) Inhibitors of the lipid and membrane synthesis, for example (10.1 ) biphenyl (92-52-4), (10.2) chloroneb (2675-77-6), (10.3) dicloran (99-30-9), (10.4) edifenphos (17109-49-8), (10.5) etridiazole (2593-15-9), (10.6) iodocarb (55406-53-6), (10.7) iprobenfos (26087-47-8), (10.8) isoprothiolane (50512-35-1 ), (10.9) propamocarb (25606-41-1 ), (10.10) propamocarb hydrochloride (25606-41-1 ), (10.11 ) prothiocarb (19622-08-3), (10.12) pyrazophos (13457-18- 6), (10.13) quintozene (82-68-8), (10.14) tecnazene (117-18-0) and (10.15) tolclofos-methyl (57018-04-9). (11 ) Inhibitors of the melanine biosynthesis, for example (11.1 ) carpropamid (104030-54-8), (11.2) diclocymet (139920-32-4), (11.3) fenoxanil (115852-48-7), (1 1.4) phthalide (27355-22-2), (11.5) pyroquilon (57369-32-1 ) and (11.6) tricyclazole (41814-78-2).
(12) Inhibitors of the nucleic acid synthesis, for example (12.1 ) benalaxyl (71626-11-4), (12.2) benalaxyl-M (98243-83-5), (12.3) bupirimate (41483-43-6), (12.4) clozylacon (67932-85-8), (12.5) dimethirimol (5221-53-4), (12.6) ethirimol (23947-60-6), (12.7) furalaxyl (57646-30-7),
(12.8) hymexazol (10004-44-1 ), (12.9) metalaxyl (57837-19-1 ), (12.10) metalaxyl-M (70630-17- 0), (12.11 ) ofurace (58810-48-3), (12.12) oxadixyl (77732-09-3) and (12.13) oxolinic acid (14698-29-4).
(13) Inhibitors of the signal transduction, for example (13.1 ) chlozolinate (84332-86-5), (13.2) fenpiclonil (74738-17-3), (13.3) fludioxonil (131341-86-1 ), (13.4) iprodione (36734-19-7), (13.5) procymidone (32809-16-8), (13.6) quinoxyfen (124495-18-7) and (13.7) vinclozolin (50471-44- 8).
(14) Compounds capable to act as an uncoupler, like for example (14.1 ) binapacryl (485-31-4), (14.2) dinocap (131-72-6), (14.3) ferimzone (89269-64-7), (14.4) fluazinam (79622-59-6) and (14.5) meptyldinocap (131-72-6).
(15) Further compounds like for example (15.1 ) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro- 1 ,2-oxazol-3-yl]-1 ,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1- yl]ethanone, (15.2) 1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl 1 H-imidazole-1- carboxylate (111227-17-9), (15.3) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine (13108-52-6), (15.4) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one (221451-58-7), (15.5) 2-[5-methyl-3- (trifluoromethyl)-1 H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1 ,2-oxazol-3-yl]-1 ,3-thiazol- 2-yl}piperidin-1-yl)ethanone, (15.6) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.7) 2- phenylphenol and salts (90-43-7), (15.8) 3,4,5-trichloropyridine-2,6-dicarbonitrile (17824-85-0),
(15.9) 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine, (15.10) 3-chloro-5-(4- chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (15.11 ) 4-(4-chlorophenyl)-5-(2,6- difluorophenyl)-3,6-dimethylpyridazine, (15.12) 5-amino-1 ,3,4-thiadiazole-2-thiol, (15.13) 5- chloro-N'-phenyl-N'-prop-2-yn-1-ylthiophene-2-sulfonohydrazide (134-31-6), (15.14) 5-methyl-6- octyl-3,7-dihydro[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-amine, (15.15) ametoctradin (865318-97-4), (15.16) benthiazole (21564-17-0), (15.17) bethoxazin (163269-30-5), (15.18) capsimycin (70694-08-5), (15.19) carvone (99-49-0), (15.20) chinomethionat (2439-01-2), (15.21 ) chlazafenone (688046-61-9), (15.22) cufraneb (1 1096-18-7), (15.23) cyflufenamid (180409-60- 3), (15.24) cymoxanil (57966-95-7), (15.25) cyprosulfamide (221667-31-8), (15.26) dazomet (533-74-4), (15.27) debacarb (62732-91-6), (15.28) dichlorophen (97-23-4), (15.29) diclomezine (62865-36-5), (15.30) difenzoquat (43222-48-6), (15.31 ) difenzoquat methylsulphate (43222-48- 6), (15.32) diphenylamine (122-39-4), (15.33) ecomate, (15.34) ethyl (2Z)-3-amino-2-cyano-3- phenylprop-2-enoate, (15.35) flumetover (154025-04-4), (15.36) fluoroimide (41205-21-4), (15.37) flusulfamide (106917-52-6), (15.38) flutianil (304900-25-2), (15.39) fosetyl-aluminium (39148-24-8), (15.40) fosetyl-calcium, (15.41 ) fosetyl-sodium (39148-16-8), (15.42) hexachlorobenzene (118-74-1 ), (15.43) irumamycin (81604-73-1 ), (15.44) methasulfocarb (66952-49-6), (15.45) methyl isothiocyanate (556-61-6), (15.46) metrafenone (220899-03-6), (15.47) mildiomycin (67527-71-3), (15.48) N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1- yloxy)phenyl]propanamide, (15.49) N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2- yn-1-yloxy)phenyl]propanamide, (15.50) N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4- dichloropyridine-3-carboxamide, (15.51 ) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4- dichloropyridine-3-carboxamide, (15.52) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4- iodopyridine-3-carboxamide, (15.53) N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)- 2,3-difluorophenyl]methyl}-2-phenylacetamide, (15.54) N-{(Z)-[(cyclopropylmethoxy)imino][6- (difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide (221201-92-9), (15.55) natamycin (7681-93-8), (15.56) nickel dimethyldithiocarbamate (15521-65-0), (15.57) nitrothal- isopropyl (10552-74-6), (15.58) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1- yljacetylJpiperidin^-yO-N^I ^.S^-tetrahydronaphthalen-i-yO-I .S-thiazole^-carboxannide, (15.59) N-methyl^i-ltS-methyl-S-OrifluoromethyO-I H-pyrazol-i-yllacetylJpiperidin^-yO-N- [(1 R)-1 ,2,3,4-tetrahydronaphthalen-1-yl]-1 ,3-thiazole-4-carboxamide, (15.60) octhilinone (26530-20-1 ), (15.61 ) oxamocarb (917242-12-7), (15.62) oxyfenthiin (34407-87-9), (15.63) pentachlorophenol and salts (87-86-5), (15.64) pentyl {6-[({[(1-methyl-1 H-tetrazol-5- yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.65) phenazine-1- carboxylic acid, (15.66) phenothrin, (15.67) phosphorous acid and its salts (13598-36-2), (15.68) propamocarb-fosetylate, (15.69) propanosine-sodium (88498-02-6), (15.70) proquinazid (189278-12-4), (15.71 ) pyrrolnitrine (1018-71-9) (known from EP-A 1 559 320), (15.72) quinolin- 8-ol (134-31-6), (15.73) quinolin-8-ol sulfate (2:1 ) (salt) (134-31-6), (15.74) fenpyrazamine (473798-59-3), (15.75) tebufloquin (376645-78-2), (15.76) tecloftalam (76280-91-6), (15.77) tolnifanide (304911-98-6), (15.78) triazoxide (72459-58-6), (15.79) trichlamide (70193-21-4), (15.80) zarilamid (84527-51-5) and salts thereof. For the composition according to the invention, preferred fungicide compounds B and C are independently selected in the list L2 consisting of ametoctradin, azoxystrobin, benalaxyl-M, benthiavalicarb, bixafen also known as N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-3- (difluoromethyl)-1-methyl-1 H-pyrazole-4-carboxamide, boscalid, chlorothalonil, copper hydroxide, copper oxychloride, cyazofamid, cymoxanil, dimethomorph, epoxiconazole, famoxadone, fenamidone, fenhexamid, fluazinam, fludioxonil, fluopicolide, fluopyram also known as N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide, fluoxastrobin, fluquinconazole, folpet, fosetyl-aluminium, iprodione, iprovalicarb, isopyrazam, mancozeb, mandipropamid, mefenoxam, metiram, penflufen, penthiopyrad, prochloraz, phosphorous acid, propamocarb, propamocarb-fosetylate, propamocarb hydrochloride, propiconazole, propineb, prothioconazole, pyraclostrobin, pyrimethanil, sedaxane, tebuconazole, triadimenol, trifloxystrobin, zoxamide, N-methyl-2-(1-{[5-methyl-3- (trifluoromethy^-I H-pyrazol-i-yllacetylJpiperidin^-y^-N-^I R^I ^.S^-tetrahydronaphthalen-i- yl]-1 ,3-thiazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-1 H- pyrazole-4-carboxamide and N-[2-(1 ,3-dimethyl-butyl)-phenyl]-5-fluoro-1 ,3-dimethyl-1 H- pyrazole-4-carboxamide.
In a particular embodiment, this invention is directed to mixtures comprising at least the compound A [but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}- oxy)methyl]pyridin-2-yl}carbamate] and one fungicide compound selected from the compounds listed in List L1.
In a more preferred embodiment this invention is directed to mixtures comprising at least the compound A and one fungicide compound selected from the compounds listed in List L2.
For the different aspects of the composition according to the invention, insecticide compound D is preferably selected in the list L3 consisting of:
(D1 ) Acetylcholinesterase (AChE) inhibitors, for example carbamates, e.g. alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thio- fanox, triazamate, trimethacarb, XMC, and xylylcarb; or organophosphates, e.g. acephate, azamethiphos, azinphos (-methyl, -ethyl), cadusafos, chlorethoxyfos, chlorfenvinphos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl), coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, isofenphos, isopropyl O-(methoxyanninothio- phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion (-methyl), phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos (-methyl), profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, and vamidothion.
(D2) GABA-gated chloride channel antagonists, for example organochlorines, e.g. chlordane, endosulfan (alpha-); or fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, pyrafluprole, and pyriprole.
(D3) Sodium channel modulators/voltage-dependent sodium channel blockers, for example pyrethroids, e.g. acrinathrin, allethrin (d-cis-trans, d-trans), bifenthrin, bioallethrin, bioallethrin S- cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin (beta-), cyhalothrin (gamma-, lambda-), cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin [(I R)-trans-isomers], deltamethrin, dimefluthrin, empenthrin [(EZ)-(I R)-isomers), esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-), halfenprox, imiprothrin, metofluthrin, permethrin, phenothrin [(I R)-trans-isomer), prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, RU 15525, silafluofen, tefluthrin, tetramethrin [(1 R)- isomers)], tralomethrin, transfluthrin and ZXI 8901 ; or DDT; or methoxychlor.
(D4) Nicotinergic acetylcholine receptor agonists, for example chloronicotinyls, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam,; or nicotine.. (D5) Allosteric acetylcholine receptor modulators (agonists), for example spinosyns, e.g. spinetoram and spinosad.
(D6) Chloride channel activators, for example avermectins/milbemycins, e.g. abamectin, emamectin benzoate, lepimectin, and milbemectin.
(D7) Juvenile hormone mimics, e.g. hydroprene, kinoprene, methoprene; or fenoxycarb; pyriproxyfen.
(D8) Miscellaneous non-specific (multi-site) inhibitors, for example gassing agents, e.g. methyl bromide and other alkyl halides; or chloropicrin; sulfuryl fluoride; borax; tartar emetic.
(D9) Selective homopteran feeding blockers, e.g. pymetrozine; or flonicamid. (D10) Mite growth inhibitors, e.g. clofentezine, diflovidazin, hexythiazox, etoxazole. (D11 ) Microbial disruptors of insect midgut membranes, e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT crop proteins: CrylAb, CryiAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1. (D12) Inhibitors of mitochondrial ATP synthase, for example diafenthiuron; or organotin miticides, e.g. azocyclotin, cyhexatin, and fenbutatin oxide; or propargite; tetradifon.
(D13) Uncouplers of oxidative phoshorylation via disruption of the proton gradient, for example chlorfenapyr, and DNOC.
(D14) Nicotinic acetylcholine receptor channel blockers, for example bensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.
(D15) Inhibitors of chitin biosynthesis, type 0, for example benzoylureas, e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, and triflumuron.
(D16) Inhibitors of chitin biosynthesis, type 1 , for example buprofezin.
(D17) Moulting disruptors, for example cyromazine.
(D18) Ecdysone receptor agonists/disruptors, for example diacylhydrazines, e.g. chromafenozide, halofenozide, methoxyfenozide, and tebufenozide. (D19) Octopamine receptor agonists, for example amitraz.
(D20) Mitochondrial complex III electron transport inhibitors (Coupling site II), for example hydramethylnon; acequinocyl; fluacrypyrim; or cyflumetofen and cyenopyrafen.
(D21 ) Mitochondrial complex I electron transport inhibitors, for example
METI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; or rotenone.(Derris).
(D22) Voltage-dependent sodium channel blockers, e.g. indoxacarb; metaflumizone.
(D23) Inhibitors of acetyl CoA carboxylase, for example tetronic acid derivatives, e.g. spirodiclofen and spiromesifen; or tetramic acid derivatives, e.g. spirotetramat.
(D24) Mitochondrial complex IV electron inhibitors, for example phosphines, e.g. aluminium phosphide, calcium phosphide, phosphine, and zinc phosphide; or cyanide.
(D28) Ryanodine receptor modulators, for example diamides, e.g. chlorantraniliprole (Rynaxypyr), Cyantraniliprole (Cyazypyr), and flubendiamide. Further active ingredients with unknown or uncertain mode of action, for example azadirachtin, amidoflumet, benzoximate, bifenazate, chinomethionat, cryolite, dicofol, flufenerim, pyridalyl, and pyrifluquinazon; or one of the following known active compounds
4-{[(6-brompyrid-3-yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (known from WO 2007/115644), 4-{[(6-fluorpyrid-3-yl)methyl](2,2-difluorethyl)amino}furan-2(5H)-on (known from WO 2007/115644), 4-{[(2-chlor-1 ,3-thiazol-5-yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (known from WO 2007/115644), 4-{[(6-chlorpyrid-3-yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (known from WO 2007/ 115644), 4-{[(6-chlorpyrid-3-yl)methyl](2,2-difluorethyl)amino}furan-2(5H)-on known from WO 2007/115644), 4-{[(6-chlor-5-fluorpyrid-3-yl)methyl](methyl)amino}furan-2(5H)- on (known from WO 2007/115643), 4-{[(5,6-dichlorpyrid-3-yl)methyl](2-fluorethyl)amino}furan- 2(5H)-on (known from WO 2007/115646), 4-{[(6-chlor-5-fluorpyrid-3- yl)methyl](cyclopropyl)amino}furan-2(5H)-on (known from WO 2007/115643), 4-{[(6-chlorpyrid- 3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on (known from EP-A-O 539 588), 4-{[(6-chlorpyrid- 3-yl)methyl](methyl)amino}furan-2(5H)-on (known from EP-A-O 539 588), [(6-chlorpyridin-3- yl)methyl](methyl)oxido-λ4-sulfanylidencyanamid (known from WO 2007/149134), [1-(6- chlorpyridin-3-yl)ethyl](methyl)oxido-λ4-sulfanylidencyanamid (known from WO 2007/149134) and its diastereomeres (A) and (B)
Figure imgf000019_0001
(A) (B)
(also known from WO 2007/149134), [(6-trifluormethylpyridin-3-yl)methyl](methyl)oxido-λ4- sulfanylidencyanamid (known from WO 2007/095229), or sulfoxaflor (also known from WO 2007/149134),
H^-chloro^.θ-dimethylphenyO-^-hydroxy-i ^-dioxa-θ-azadispiro^^^^ltetradec-H-en-IO- one
(known from WO 2006/089633), 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1- azaspiro[4.5]dec-3-en-2-one (known from WO 2008/067911 ), and 1-{2,4-dimethyl-5-[(2,2,2- trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1 H-1 ,2,4-triazole (known from WO 1999/55668). The active ingredients specified in this description by their "common name" are known, for example, from "The Pesticide Manual", 13th Ed., British Crop Protection Council 2003, and from the Web page http://www.alanwood.net/pesticides.
For the various aspects of the composition according to the invention, more preferred insecticide compounds are selected in the list L4 consisting of imidacloprid and clothianidin.
In a particular embodiment, this invention is directed to mixtures comprising at least the compound A [but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}- oxy)methyl]pyridin-2-yl}carbamate] and one insecticidal compound selected from the compounds listed in List L3.
In a more preferred embodiment this invention is directed to mixtures comprising at least the compound A and one insecticidal compound selected from the compounds listed in List L4.
For the composition according to the invention, the A/B weight ratio preferably ranges from 1/0.01 to 1/100; more preferably from 1/0.05 to 1/80.
For the composition according to the invention, the A/B/C or A/B/D weight ratio preferably ranges from 1/0.01/0.01 to 1/100/100; more preferably from 1/0.05/0.05 to 1/80/80.
For the composition according to the invention, the A/B/C/D weight ratio preferably ranges from 1/0.01/0.01/0.1 to 1/100/100/100; more preferably from 1/0.05/0.05/0.5 to 1/80/80/80.
Particular compositions according to the invention are defined as combining all or part of:
- preferred oxime compounds of formula (I) as herein-defined; - preferred fungicide compounds B;
- preferred fungicide compounds C;
- preferred insecticide compounds D;
- preferred weight ratios of active substances.
According to another aspect of the present invention, in the pesticide composition according to the invention, the compound ratio A/B can be advantageously selected so as to produce a synergistic effect. The term synergistic effect is understood to mean in particular that defined by Colby in an article entitled "Calculation of the synergistic and antagonistic responses of herbicide combinations" Weeds, (1967), 15, pages 20-22. The latter article mentions the formula: XY
E = X+Y —
100 wherein E represents the expected percentage of inhibition of the pest for the combination of the two compounds at defined doses (for example equal to x and y respectively), X is the percentage of inhibition observed for the pest by compound A at a defined dose (equal to x), Y is the percentage of inhibition observed for the pest by compound B at a defined dose (equal to y). When the percentage of inhibition observed for the combination is greater than E, there is a synergistic effect.
The term "synergistic effect" also means the effect defined by application of the Tammes method, "Isoboles, a graphic representation of synergism in pesticides", Netherlands Journal of Plant Pathology, 70(1964), pages 73-80.
According to another aspect of the present invention, in the pesticide composition according to the invention, the compound ratio A/B/C can be advantageously selected so as to produce a synergistic effect. The term synergistic effect is understood to mean in particular that defined by Colby in an article entitled "Calculation of the synergistic and antagonistic responses of herbicide combinations" Weeds, (1967), 15, pages 20-22. The latter article mentions the formula:
E= X+Y + Z-^- 100 wherein E represents the expected percentage of inhibition of the pest for the combination of the three compounds at defined doses (for example equal to x, y and z respectively), X is the percentage of inhibition observed for the pest by compound A at a defined dose (equal to x), Y is the percentage of inhibition observed for the pest by compound B at a defined dose (equal to y) and Z is the percentage of inhibition observed for the pest by compound C at a defined dose (equal to z). When the percentage of inhibition observed for the combination is greater than E, there is a synergistic effect. The term "synergistic effect" also means the effect defined by application of the Tammes method, "Isoboles, a graphic representation of synergism in pesticides", Netherlands Journal of Plant Pathology, 70(1964), pages 73-80.
Synergistic compositions comprising further active substances also form part of the present invention, the associated synergistic effect can be evidenced in a similar manner.
The pesticide composition according to the invention may comprise from 0.00001 to 100%, preferably from 0.001 to 80%, of active compounds, whether these compounds are combined or whether they are in the form of two or more active ingredients used separately. More generally, the pesticide composition according to the invention may eventually also comprise one or more other active substances selected from fungicide, herbicide, insecticide or plant growth regulator active compounds.
In addition to these additional active agents, the pesticide composition according to the invention may also comprise any other adjuvants or auxiliary agent useful in plant protection formulations such as, for example, an agriculturally suitable inert carrier and optionally an agriculturally suitable surfactant.
For its practical use, the pesticide composition according to the invention can be used alone or in formulations containing one or the other of the active ingredients or alternatively both of them together, in combination or association with one or more other compatible components which are, for example, solid or liquid fillers or diluents, adjuvants, surfactants or equivalents, which are suitable for the desired use and which are acceptable for uses in agriculture. The formulations can be of any type known in the sector that is suitable for application onto all types of cultures or crops. These formulations, which can be prepared in any manner known by the skilled person, also form part of the invention.
The formulations may also contain ingredients of other types, such as protective colloids, adhesives, thickeners, thixotropic agents, penetrating agents, oils for spraying, stabilisers, preserving agents (in particular mould-proofing or biocide agents), sequestering or chelating agents or the like. More generally, the compounds used in the invention can be combined with any solid or liquid additives corresponding to the usual formulation techniques.
The term "filler" means an organic or inorganic, natural or synthetic component with which the active components are combined to facilitate its application, for example, onto the plants, the seeds or the soil. This filler is consequently generally inert and it must be acceptable (for example acceptable for agronomic uses, in particular for treating plants). The filler can be solid, for example clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers (for example ammonium salts), natural soil minerals, such as kaolins, clays, talc, lime, quartz, attapulgite, montmorillonite, bentonite or diatomaceous earths or synthetic minerals, such as silica, alumina or silicates, in particular aluminium or magnesium silicates. The solid fillers which are suitable for granules are as follows: natural, crushed or broken rocks, such as calcite, marble, pumice, sepiolite and dolomite; synthetic granules of inorganic or organic flours; granules of organic material such as sawdust, coconut shell, corn ear or envelope or tobacco stem; kieselguhr, tricalcium phosphate, powdered cork or adsorbent carbon black; water-soluble polymers, resins, waxes; or solid fertilizers. Such composition may, if so desired, contain one or more compatible agents such as wetting agents, dispersing agents, emulsifiers or colourings which, when they are solid, may also act as diluents. The fillers may also be liquid, for example: water, alcohols, in particular butanol or glycol, as well as ethers or esters thereof, in particular methyl glycol acetate; ketones, in particular acetone, cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone or isophorone; petroleum fractions such as paraffinic or aromatic hydrocarbons, in particular xylenes or alkylnaphthalenes; mineral or plant oils; aliphatic chlorohydrocarbons, in particular trichloroethane or methylene chloride; aromatic chlorohydrocarbons, in particular chlorobenzenes; water-soluble or highly polar solvents such as dimethylformamide, dimethyl sulphoxide, N,N-dimethyl-acetamide or N- methylpyrrolidone; N-octylpyrrolidone, liquefied gases; or the like, whether they are taken separately or as a mixture. The surfactant can be an emulsifier, a dispersing agent or a wetting agent, of ionic or nonionic type or a mixture of these surfactants. Among those surfactants there are used, for example, polyacrylic acid salts, lignosulphonic acid salts, phenolsulphonic or naphthalenesulphonic acid salts, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty esters or fatty amines, substituted phenols (in particular alkylphenols or arylphenols), ester-salts of sulphosuccinic acid, taurine derivatives (in particular alkyl taurates), phosphoric esters of alcohols or of polycondensates of ethylene oxide with phenols, fatty acid esters with polyols or sulphate, sulphonate or phosphate functional derivatives of the compounds described above. The presence of at least one surfactant is generally essential when the active ingredients and/or the inert filler are insoluble or only sparingly soluble in water and when the filler for the said composition to be applied is water.
The formulations may also contain other additives such as adhesives or dyes. Adhesives such as carboxymethylcellulose or natural or synthetic polymers in the form of powders, granules or matrices, such as gum arabic, latex, polyvinylpyrrolidone, polyvinyl alcohol or polyvinyl acetate, natural phospholipids, such as cephalins or lecithins or synthetic phospholipids can be used in the formulations. It is possible to use colourings such as inorganic pigments, such as, for example: iron oxides, titanium oxides, Prussian blue; organic colouring stuffs, such as those of the alizarin, azo or metal phthalocyanin type; or of trace elements such as iron, manganese, boron, copper, cobalt, molybdenum or zinc salts.
The form of the pesticide composition according to the invention can be selected in a large number of formulations, such as aerosol dispenser; suspension of capsules; cold fogging concentrate; dustable powder; emulsifiable concentrate; aqueous/aqueous type emulsion; oil/inverse type emulsion; encapsulated granule; fine granule; suspension concentrate for seed treatment; compressed gas; gas generating product; granule; hot fogging concentrate; macrogranule; microgranule; oil-dispersible powder; oil miscible suspension concentrate; oil- miscible liquid; paste; plant rodlet; powder for dry seed treatment; seeds coated with a pesticide; smoke maydle; smoke cartridge; smoke generator; smoke pellet; smoke rodlet; smoke tablet; smoke tin; soluble concentrate; soluble powder; solution for seed treatment; suspension concentrate (= flowable concentrate); ultra low volume liquid; ultra low volume suspension; vapour releasing product; water-dispersible granules or tablets; water dispersible powder for slurry treatment; water-soluble granules or tablets; water-soluble powder for seed treatment; wettable powder.
The pesticide composition according to the present invention covers not only the compositions which are ready to be applied to the crop by means of a suitable device, such as a spraying device, but also the commercial concentrated composition which have to be diluted before application to the crop.
The pesticide composition herein described is used in general for application to growing plants or to sites where crops are grown or intended to grow or for the treatment, coating or film- coating of seeds.
According to the present invention, seeds may comprise any propagation materials, like for example seeds, fruit, tubers, grains, roots, rhizomes, parts of plants.
The pesticide composition according to the invention may also be applied to the vegetation and in particular to the leaves infested or capable of being infested with the phytopathogenic fungi or damaged by insects. Another method of applying the pesticide composition according to the invention is to add a formulation containing the active ingredients to the irrigation water.
According to another object of the present invention, there is provided a method for controlling the phytopathogenic fungi or damaging insects of plants, crops or seeds, characterized in that an agronomically effective and substantially non-phytotoxic quantity of a pesticide composition according to the invention is applied as seed treatment, foliar application, stem application, drench or drip application (chemigation) to the seed, the plant or to the fruit of the plant or to soil or to inert substrate (e.g. inorganic substrates like sand, rockwool, glasswool; expanded minerals like perlite, vermiculite, zeolite or expanded clay), Pumice, Pyroclastic materials or stuff, synthetic organic substrates (e.g. polyurethane) organic substrates (e.g. peat, composts, tree waste products like coir, wood fibre or chips, tree bark) or to a liquid substrate (e.g. floating hydroponic systems, Nutrient Film Technique, Aeroponics) wherein the plant is growing or wherein it is desired to grow. The expression "are applied to the plants to be treated" is understood to mean, for the purposes of the present invention, that the pesticide composition which is the subject of the invention can be applied by means of various methods of treatment such as:
- spraying onto the aerial parts of the said plants a liquid comprising one of the said compositions,
- dusting, the incorporation into the soil of granules or powders, spraying, around the said plants, and in the case of trees injection or daubing,
- coating or film-coating the seeds of the said plants with the aid of a plant-protection mixture comprising one of the said compositions. The method according to the invention may either be a curing, preventing or eradicating method.
In this method, a composition used can be prepared beforehand by mixing the two or more active compounds according to the invention.
According to an alternative of such a method, it is also possible to apply simultaneously, successively or separately compounds (A), (B), (C) or (D) so as to have the conjugated (A)/(B)
/(C)/(D) effects, of distinct compositions each containing one or more active ingredients (A), (B),
(C) or (D).
The dose of active compound usually applied in the method of treatment according to the invention is generally and advantageously
- for foliar treatments: from 0.1 to 10,000 g/ha, preferably from 10 to 1 ,000 g/ha, more preferably from 50 to 300g/ha; in case of drench or drip application, the dose can even be reduced, especially while using inert substrates like rockwool or perlite;
- for seed treatment: from 2 to 200 g per 100 kilogram of seed, preferably from 3 to 15O g per 100 kilogram of seed;
- for soil treatment: from 0.1 to 10,000 g/ha, preferably from 1 to 5,000 g/ha.
The doses herein indicated are given as illustrative Examples of method according to the invention. A person skilled in the art will know how to adapt the application doses, notably according to the nature of the plant or crop to be treated. Under specific conditions, for example according to the nature of the phytopathogenic fungus to be treated or insect to control, a lower dose may offer adequate protection. Certain climatic conditions, resistance or other factors like the nature of the phytopathogenic fungi or damaging insect to be eliminated or the degree of infestation, for example, of the plants with these fungi, may require higher doses of combined active ingredients. The optimum dose usually depends on several factors, for example on the type of phytopathogenic fungus to be treated or insect to control, on the type or level of development of the infested plant, on the density of vegetation or alternatively on the method of application.
Without it being limiting, the crop treated with the pesticide composition or combination according to the invention is, for example, grapevine, but this could be cereals, vegetables, lucerne, soybean, market garden crops, turf, wood, tree or horticultural plants. The method of treatment according to the invention may also be useful to treat propagation material such as tubers or rhizomes, but also seeds, seedlings or seedlings pricking out and plants or plants pricking out. This method of treatment may also be useful to treat roots. The method of treatment according to the invention may also be useful to treat the over-ground parts of the plant such as trunks, stems or stalks, leaves, flowers and fruit of the concerned plant. Among the plants that may becan be protected by the method according to the invention, mention may becan be made of cotton; flax; vine; fruit or vegetable crops such as Rosaceae sp. (for instance pip fruit such as apples and pears, but also stone fruit such as apricots, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana trees and plantins), Rubiaceae sp., Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemons oranges and grapefruit); Solanaceae sp. (for instance tomatoes), ϋliaceae sp., Asteraceae sp. (for instance lettuces), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp., Papilionaceae sp. (for instance peas), Rosaceae sp. (for instance strawberries); major crops such as Graminae sp. (for instance maize, lawn or cereals such as wheat, rye, rice, barley and triticale), Asteraceae sp. (for instance sunflower), Cruciferae sp. (for instance colza), Fabacae sp. (for instance peanuts), Papilionaceae sp. (for instance soybean), Solanaceae sp. (for instance potatoes), Chenopodiaceae sp. (for instance beetroots), Elaeis sp. (for instance oil palm); horticultural and forest crops; as well as genetically modified homologues of these crops.
The method of treatment according to the invention can be used in the treatment of genetically modified organisms (GMOs), e.g. plants or seeds. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The expression "heterologous gene" essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, co suppression technology or RNA interference - RNAi - technology). A heterologous gene that is located in the genome is also called a transgene. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the active compounds and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, bigger fruits, larger plant height, greener leaf color, earlier flowering, higher quality and/or a higher nutritional value of the harvested products, higher sugar concentration within the fruits, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected.
At certain application rates, the active compound combinations according to the invention may also have a strengthening effect in plants. Accordingly, they are also suitable for mobilizing the defense system of the plant against attack by unwanted phytopathogenic fungi and/ or microorganisms and/or viruses. This may, if appropriate, be one of the reasons of the enhanced activity of the combinations according to the invention, for example against fungi. Plant- strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances or combinations of substances which are capable of stimulating the defense system of plants in such a way that, when subsequently inoculated with unwanted phytopathogenic fungi and/ or microorganisms and/or viruses, the treated plants display a substantial degree of resistance to these unwanted phytopathogenic fungi and/ or microorganisms and/or viruses. In the present case, unwanted phytopathogenic fungi and/ or microorganisms and/or viruses are to be understood as meaning phytopathogenic fungi, bacteria and viruses. Thus, the substances according to the invention can be employed for protecting plants against attack by the abovementioned pathogens within a certain period of time after the treatment. The period of time within which protection is effected generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds. Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means).
Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.
Plants and plant cultivars which may also be treated according to the invention are those plants which are resistant to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozon exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.
Plants and plant cultivars which may also be treated according to the invention, are those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. Yield can furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Further yield traits include seed composition, such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability.
Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stress factors. Such plants are typically made by crossing an inbred male-sterile parent line (the female parent) with another inbred male-fertile parent line (the male parent). Hybrid seed is typically harvested from the male sterile plants and sold to growers. Male sterile plants can sometimes (e.g. in corn) be produced by detasseling, i.e. the mechanical removal of the male reproductive organs (or males flowers) but, more typically, male sterility is the result of genetic determinants in the plant genome. In that case, and especially when seed is the desired product to be harvested from the hybrid plants it is typically useful to ensure that male fertility in the hybrid plants is fully restored. This can be accomplished by ensuring that the male parents have appropriate fertility restorer genes which are capable of restoring the male fertility in hybrid plants that contain the genetic determinants responsible for male-sterility. Genetic determinants for male sterility may be located in the cytoplasm. Examples of cytoplasmic male sterility (CMS) were for instance described in Brassica species (WO 1992/005251 , WO 1995/009910, WO 1998/27806, WO 2005/002324, WO 2006/021972 and US 6,229,072). However, genetic determinants for male sterility can also be located in the nuclear genome. Male sterile plants can also be obtained by plant biotechnology methods such as genetic engineering. A particularly useful means of obtaining male-sterile plants is described in WO 1989/10396 in which, for example, a ribonuclease such as barnase is selectively expressed in the tapetum cells in the stamens. Fertility can then be restored by expression in the tapetum cells of a ribonuclease inhibitor such as barstar (e.g. WO 1991/002069).
Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.
Herbicide-tolerant plants are for example glyphosate-tolerant plants, i.e. plants made tolerant to the herbicide glyphosate or salts thereof. Plants can be made tolerant to glyphosate through different means. For example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221 , 370-371 ), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., Curr. Topics Plant Physiol. (1992), 7, 139-145), the genes encoding a Petunia EPSPS (Shah et al., Science (1986), 233, 478-481 ), a Tomato EPSPS (Gasser et al., J. Biol. Chem. (1988),263, 4280-4289), or an Eleusine EPSPS (WO 2001/66704). It can also be a mutated EPSPS as described in for example EP-A 0837944, WO 2000/066746, WO 2000/066747 or WO 2002/026995. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate oxido-reductase enzyme as described in US 5,776,760 and US 5,463,175. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate acetyl transferase enzyme as described in for example WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO 2007/024782. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally- occurring mutations of the above-mentioned genes, as described in for example WO 2001/024615 or WO 2003/013226.
Other herbicide resistant plants are for example plants that are made tolerant to herbicides inhibiting the enzyme glutamine synthase, such as bialaphos, phosphinothricin or glufosinate. Such plants can be obtained by expressing an enzyme detoxifying the herbicide or a mutant glutamine synthase enzyme that is resistant to inhibition. One such efficient detoxifying enzyme is an enzyme encoding a phosphinothricin acetyltransferase (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinothricin acetyltransferase are for example described in US 5,561 ,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665. Further herbicide-tolerant plants are also plants that are made tolerant to the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase (HPPD).
Hydroxyphenylpyruvatedioxygenases are enzymes that catalyze the reaction in which para- hydroxyphenylpyruvate (HPP) is transformed into homogentisate. Plants tolerant to HPPD- inhibitors can be transformed with a gene encoding a naturally-occurring resistant HPPD enzyme, or a gene encoding a mutated HPPD enzyme as described in WO 1996/038567, WO 1999/024585 and WO 1999/024586. Tolerance to HPPD-inhibitors can also be obtained by transforming plants with genes encoding certain enzymes enabling the formation of homogentisate despite the inhibition of the native HPPD enzyme by the HPPD-inhibitor. Such plants and genes are described in WO 1999/034008 and WO 2002/36787. Tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene encoding an enzyme prephenate dehydrogenase in addition to a gene encoding an HPPD-tolerant enzyme, as described in WO 2004/024928.
Still further herbicide resistant plants are plants that are made tolerant to acetolactate synthase (ALS) inhibitors. Known ALS-inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinone herbicides. Different mutations in the ALS enzyme (also known as acetohydroxyacid synthase, AHAS) are known to confer tolerance to different herbicides and groups of herbicides, as described for example in Tranel and Wright, Weed Science (2002), 50, 700-712, but also, in US 5,605,011 , US 5,378,824, US 5,141 ,870, and US 5,013,659. The production of sulfonylurea- tolerant plants and imidazolinone-tolerant plants is described in US 5,605,011 ; US 5,013,659; US 5,141 ,870; US 5,767,361 ; US 5,731 ,180; US 5,304,732; US 4,761 ,373; US 5,331 ,107; US 5,928,937; and US 5,378,824; and international publication WO 1996/033270. Other imidazolinone-tolerant plants are also described in for example WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351 , and WO 2006/060634. Further sulfonylurea- and imidazolinone-tolerant plants are also described in for example WO 2007/024782.
Other plants tolerant to imidazolinone and/or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or mutation breeding as described for example for soybeans in US 5,084,082, for rice in WO 1997/41218, for sugar beet in US 5,773,702 and WO 1999/057965 , for lettuce in US 5,198,599, or for sunflower in WO 2001/065922.
Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance. An "insect-resistant transgenic plant", as used herein, includes any plant containing at least one transgene comprising a coding sequence encoding:
1 ) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof, such as the insecticidal crystal proteins listed by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, updated by Crickmore et al. (2005) at the Bacillus thuringiensis toxin nomenclature, online at: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal portions thereof, e.g., proteins of the Cry protein classes CrylAb, CryiAc, Cry1 F, Cry2Ab, Cry3Aa, or Cry3Bb or insecticidal portions thereof; or 2) a crystal protein from Bacillus thuringiensis or a portion thereof which is insecticidal in the presence of a second other crystal protein from Bacillus thuringiensis or a portion thereof, such as the binary toxin made up of the Cry34 and Cry35 crystal proteins (Moellenbeck et al., Nat. Biotechnol. (2001 ), 19, 668-72; Schnepf et al., Applied Environm. Microbiol. (2006), 71 , 1765-1774); or 3) a hybrid insecticidal protein comprising parts of different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1 ) above or a hybrid of the proteins of 2) above, e.g., the Cry1A.1O5 protein produced by corn event MON98034 (WO 2007/027777); or
4) a protein of any one of 1 ) to 3) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation, such as the Cry3Bb1 protein in corn events MON863 or MON88017, or the Cry3A protein in corn event MIR604; 5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus, or an insecticidal portion thereof, such as the vegetative insecticidal (VIP) proteins listed at: http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html, e.g., proteins from the VIP3Aa protein class; or
6) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin made up of the VIP1A and VIP2A proteins (WO 1994/21795); or
7) a hybrid insecticidal protein comprising parts from different secreted proteins from Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins in 1 ) above or a hybrid of the proteins in 2) above; or
8) a protein of any one of 1 ) to 3) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation (while still encoding an insecticidal protein), such as the VIP3Aa protein in cotton event COT102.
Of course, an insect-resistant transgenic plant, as used herein, also includes any plant comprising a combination of genes encoding the proteins of any one of the above classes 1 to 8. In one embodiment, an insect-resistant plant contains more than one transgene encoding a protein of any one of the above classes 1 to 8, to expand the range of target insect species affected when using different proteins directed at different target insect species, or to delay insect resistance development to the plants by using different proteins insecticidal to the same target insect species but having a different mode of action, such as binding to different receptor binding sites in the insect.
Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance. Particularly useful stress tolerance plants include: a. plants which contain a transgene capable of reducing the expression and/or the activity of poly(ADP-ribose)polymerase (PARP) gene in the plant cells or plants as described in WO 2000/004173 or WO2006/045633 or PCT/EP07/004142.
b. plants which contain a stress tolerance enhancing transgene capable of reducing the expression and/or the activity of the PARG encoding genes of the plants or plants cells, as described e.g. in WO 2004/090140.
c. plants which contain a stress tolerance enhancing transgene coding for a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage synthesis pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyl transferase, nicotinamide adenine dinucleotide synthetase or nicotine amide phosphoribosyltransferase as described e.g. in WO2006/032469 or WO 2006/133827 or PCT/EP07/002433.
Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention show altered quantity, quality and/or storage-stability of the harvested product and/or altered properties of specific ingredients of the harvested product such as : 1 ) transgenic plants which synthesize a modified starch, which in its physical-chemical characteristics, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the side chain distribution, the viscosity behaviour, the gelling strength, the starch grain size and/or the starch grain morphology, is changed in comparison with the synthesised starch in wild type plant cells or plants, so that this is better suited for special applications. Said transgenic plants synthesizing a modified starch are disclosed, for example, in EP 0571427, WO 1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581 , WO 1996/27674, WO 1997/1 1188, WO 1997/26362, WO 1997/32985, WO 1997/42328, WO 1997/44472, WO 1997/45545, WO 1998/27212, WO 1998/40503, WO99/58688, WO 1999/58690, WO 1999/58654, WO 2000/008184, WO 2000/008185, WO 2000/008175, WO 2000/28052,
WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941 , WO 2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823, WO 2000/22140, WO 2006/063862, WO 2006/072603, WO 2002/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1 , EP 07090009.7, WO 2001/14569, WO 2002/79410, WO 2003/33540, WO 2004/078983, WO 2001/19975, WO 1995/26407, WO 1996/34968, WO 1998/20145, WO 1999/12950,
WO 1999/66050, WO 1999/53072, US 6,734,341 , WO 2000/11 192, WO 1998/22604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US 6,013,861 , WO 1994/004693, WO 1994/009144, WO 1994/11520, WO 1995/35026, WO 1997/20936. 2) transgenic plants which synthesize non starch carbohydrate polymers or which synthesize non starch carbohydrate polymers with altered properties in comparison to wild type plants without genetic modification. Examples are plants producing polyfructose, especially of the inulin and levan-type, as disclosed in EP 0663956, WO 1996/001904, WO 1996/021023, WO 1998/039460, and WO 1999/024593, plants producing alpha 1 ,4 glucans as disclosed in WO 1995/031553, US 2002/031826, US
6,284,479, US 5,712,107, WO 1997/047806, WO 1997/047807, WO 1997/047808 and WO 2000/014249, plants producing alpha-1 ,6 branched alpha-1 ,4-glucans, as disclosed in WO 2000/73422, plants producing alternan, as disclosed in WO 2000/047727, EP 06077301.7, US 5,908,975 and EP 0728213, 3) transgenic plants which produce hyaluronan, as for example disclosed in WO
2006/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006/304779, and WO 2005/012529.
Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics and include: a) Plants, such as cotton plants, containing an altered form of cellulose synthase genes as described in WO 1998/000549 b) Plants, such as cotton plants, containing an altered form of rsw2 or rsw3 homologous nucleic acids as described in WO2004/053219 c) Plants, such as cotton plants, with increased expression of sucrose phosphate synthase as described in WO 2001/017333 d) Plants, such as cotton plants, with increased expression of sucrose synthase as described in WO02/45485 e) Plants, such as cotton plants, wherein the tinning of the plasmodesmatal gating at the basis of the fiber cell is altered, e.g. through downregulation of fiberselective β 1 ,3-glucanase as described in WO2005/017157 f) Plants, such as cotton plants, having fibers with altered reactivity, e.g. through the expression of N-acteylglucosaminetransferase gene including nodC and chitinsynthase genes as described in WO2006/136351
Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation or by selection of plants contain a mutation imparting such altered oil characteristics and include: a) Plants, such as oilseed rape plants, producing oil having a high oleic acid content as described e.g. in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947 b) Plants such as oilseed rape plants, producing oil having a low linolenic acid content as described in US 6,270828, US 6,169,190 or US 5,965,755 c) Plant such as oilseed rape plants, producing oil having a low level of saturated fatty acids as described e.g. in US 5,434,283
Particularly useful transgenic plants which may be treated according to the invention are plants which comprise one or more genes which encode one or more toxins, such as the following which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), BiteGard® (for example maize), Bt-Xtra® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B®(cotton), NatureGard® (for example maize), Protecta® and NewLeaf® (potato). Examples of herbicide- tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Particularly useful transgenic plants which may be treated according to the invention are plants containing transformation events, or combination of transformation events, that are listed for example in the databases from various national or regional regulatory agencies (see for example http://gmoinfo.jrc.it/gmp_browse.aspx and http://www.agbios.com/dbase.php).
The composition according to the invention may also be used against fungal diseases liable to grow on or inside timber. The term "timber" means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood. The method for treating timber according to the invention mainly consists in contacting one or more compounds according to the invention or a composition according to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means.
Among the diseases of plants or crops that can be controlled by the method according to the invention, mention can be made of :
Powdery Mildew Diseases such as
Blumeria diseases caused for example by Blumeria graminis;
Podosphaera diseases caused for example by Podosphaera leucotricha;
Sphaerotheca diseases caused for example by Sphaerotheca fuliginea; Uncinula diseases caused for example by Uncinula necator;
Rust Diseases such as
Gymnosporangium diseases caused for example by Gymnosporangium sabinae; Hemileia diseases caused for example by Hemileia vastatrix; Phakopsora diseases caused for example by Phakopsora pachyrhizi and Phakopsora meibomiae;
Puccinia diseases caused for example by Puccinia recondita, Puccinia graminis or Puccinia striiformis; Uromyces diseases caused for example by Uromyces append iculatus;
Oomycete Diseases such as
Albugo diseases caused for example by Albugo Candida; Bremia diseases caused for example by Bremia lactucae;
Peronospora diseases caused for example by Peronospora pisi and Peronospora brassicae; Phytophthora diseases caused for example by Phytophthora infestans; Plasmopara diseases caused for example by Plasmopara viticola;
Pseudoperonospora diseases caused for example by Pseudoperonospora humuli and Pseudo- peronospora cubensis;
Pythium diseases caused for example by Pythium ultimum;
Leaf spot, Leaf blotch and Leaf Blight Diseases such as
Alternaria diseases caused for example by Alternaria solani;
Cercospora diseases caused for example by Cercospora beticola;
Cladiosporium diseases caused for example by Cladiosporium cucumerinum; Cochliobolus diseases caused for example by Cochliobolus sativus (Conidiaform: Drechslera,
Syn: Helminthosporium) or Cochliobolus miyabeanus;
Colletotrichum diseases caused for example by Colletotrichum lindemuthianum;
Cycloconium diseases caused for example by Cycloconium oleaginum;
Diaporthe diseases caused for example by Diaporthe citri; Elsinoe diseases caused for example by Elsinoe fawcettii;
Gloeosporium diseases caused for example by Gloeosporium laeticolor;
Glomerella diseases caused for example by Glomerella cingulata;
Guignardia diseases caused for example by Guignardia bidwellii;
Leptosphaeria diseases caused for example by Leptosphaeria maculans and Leptosphaeria nodorum;
Magnaporthe diseases caused for example by Magnaporthe grisea;
Mycosphaerella diseases caused for example by Mycosphaerella graminicola, Mycosphaerella arachidicola and Mycosphaerella fijiensis;
Phaeosphaeria diseases caused for example by Phaeosphaeria nodorum; Pyrenophora diseases caused for example by Pyrenophora teres or Pyrenophora tritici repentis;
Ramularia- diseases caused for example by Ramularia collo-cygni or Ramularia areola;
Rhynchosporium diseases caused for example by Rhynchosporium secalis;
Septoria diseases caused for example by Septoria apii and Septoria lycopersici;
Typhula diseases caused for example by Thyphula incarnata; Venturia diseases caused for example by Venturia inaequalis;
Root-, Sheath and Stem Diseases such as
Corticium diseases caused for example by Corticium graminearum; Fusarium diseases caused for example by Fusarium oxysporum; Gaeumannomyces diseases caused for example by Gaeumannomyces graminis; Rhizoctonia diseases caused for example by Rhizoctonia solani; Sarocladium diseases caused for example by Sarocladium oryzae; Sclerotium diseases caused for example by Sclerotium oryzae; Tapesia diseases caused for example by Tapesia acuformis; Thielaviopsis diseases caused for example by Thielaviopsis basicola;
Ear and Panicle Diseases including Maize cob such as Alternaria diseases caused for example by Alternaria spp.; Aspergillus diseases caused for example by Aspergillus flavus; Cladosporium diseases caused for example by Cladiosporium cladosporioides; Claviceps diseases caused for example by Claviceps purpurea; Fusarium diseases caused for example by Fusarium culmorum; Gibberella diseases caused for example by Gibberella zeae; Monographella diseases caused for example by Monographella nivalis;
Smut- and Bunt Diseases such as
Sphacelotheca diseases caused for example by Sphacelotheca reiliana; Tilletia diseases caused for example by Tilletia caries; Urocystis diseases caused for example by Urocystis occulta; Ustilago diseases caused for example by Ustilago nuda;
Fruit Rot and Mould Diseases such as
Aspergillus diseases caused for example by Aspergillus flavus; Botrytis diseases caused for example by Botrytis cinerea; Penicillium diseases caused for example by Penicillium expansum and Penicillium purpurogenum;
Rhizopus diseases caused by example by Rhizopus stolonifer Sclerotinia diseases caused for example by Sclerotinia sclerotiorum; Verticillium diseases caused for example by Verticillium alboatrum;
Seed- and Soilborne Decay, Mould, Wilt, Rot and Damping-off diseases Alternaria diseases caused for example by Alternaria brassicicola; Aphanomyces diseases caused for example by Aphanomyces euteiches; Ascochyta diseases caused for example by Ascochyta lentis; Aspergillus diseases caused for example by Aspergillus flavus; Cladosporium diseases caused for example by Cladosporium herbarum;
Cochliobolus diseases caused for example by Cochliobolus sativus;
(Conidiaform: Drechslera, Bipolaris Syn: Helminthosporium);
Colletotrichum diseases caused for example by Colletotrichum coccodes; Fusarium diseases caused for example by Fusarium culmorum;
Gibberella diseases caused for example by Gibberella zeae;
Macrophomina diseases caused for example by Macrophomina phaseolina;
Microdochium diseases caused for example by Microdochium nivale;
Monographella diseases caused for example by Monographella nivalis; Penicillium diseases caused for example by Penicillium expansum;
Phoma diseases caused for example by Phoma lingam;
Phomopsis diseases caused for example by Phomopsis sojae;
Phytophthora diseases caused for example by Phytophthora cactorum;
Pyrenophora diseases caused for example by Pyrenophora graminea; Pyricularia diseases caused for example by Pyricularia oryzae;
Pythium diseases caused for example by Pythium ultimum;
Rhizoctonia diseases caused for example by Rhizoctonia solani;
Rhizopus diseases caused for example by Rhizopus oryzae;
Sclerotium diseases caused for example by Sclerotium rolfsii; Septoria diseases caused for example by Septoria nodorum;
Typhula diseases caused for example by Typhula incarnata;
Verticillium diseases caused for example by Verticillium dahliae;
Canker, Broom and Dieback Diseases such as Nectria diseases caused for example by Nectria galligena;
Blight Diseases such as
Monilinia diseases caused for example by Monilinia laxa;
Leaf Blister or Leaf Curl Diseases including deformation of blooms and fruits such as Exobasidium diseases caused for example by Exobasidium vexans. Taphrina diseases caused for example by Taphrina deformans;
Decline Diseases of Wooden Plants such as Esca disease caused for example by Phaeomoniella clamydospora, Phaeoacremonium aleophilum and Fomitiporia mediterranea;
Ganoderma diseases caused for example by Ganoderma boninense;
Rigidoporus diseases caused for example by Rigidoporus lignosus
Diseases of Flowers and Seeds such as
Botrytis diseases caused for example by Botrytis cinerea;
Diseases of Tubers such as Rhizoctonia diseases caused for example by Rhizoctonia solani;
Helminthosporium diseases caused for example by Helminthosporium solani;
Club root diseases such as
Plasmodiophora diseases, cause for example by Plamodiophora brassicae.
Diseases caused by Bacterial Organisms such as Xanthomonas species for example Xanthomonas campestris pv. oryzae; Pseudomonas species for example Pseudomonas syringae pv. lachrymans; Erwinia species for example Erwinia amylovora.
The damaging insects of crops which can be controlled at any development stage by using the pesticide composition according to the invention include:
• pests from the order of lsopoda for example Oniscus asellus, Armadillidium vulgare, Porcellio scaber; • pests from the order of Diplopoda for example Blaniulus guttulatus;
• pests from the order of Chilopoda for example Geophilus carpophagus, Scutigera spp.;
• pests from the order of Symphyla for example Scutigerella immaculata;
• pests from the order of Thysanura for example Lepisma saccharina;
• pests from the order of Collembola for example Onychiurus armatus; • pests from the order of Orthoptera for example Acheta domesticus, Gryllotalpa spp.,
Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria;
• pests from the order of Blattaria for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica;
• pests from the order of Dermaptera for example Forficula auricularia; • pests from the order of lsoptera for example Reticulitermes spp.; • pests from the order of Phthiraptera for example Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.;
• pests from the order of Thysanoptera for example Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis; • pests from the order of Heteroptera for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp;
• pests from the order of Homoptera for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli,
Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp;
• pests from the order of Lepidoptera for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella,
Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella,
Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae;
• pests from the order of Coleoptera for example Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus,
Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp. oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp.,
Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitial is, Costelytra zealandica, Lissorhoptrus oryzophilus;
• pests from the order of Hymenoptera for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp; • pests from the order of Diptera for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Os- cinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.;
• pests from the order of Siphonaptera for example Xenopsylla cheopis, Ceratophyllus spp.;
• pests from the class of Arachnida for example Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp. ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis,
Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarso- nemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp; • the plant-parasitic nematodes such as Pratylenchus spp., Radopholus similis,
Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.
As a further aspect, the present invention provides a product comprising compounds (A), (B), (C) and (D) as herein defined, as a combined preparation for simultaneous, separate or sequential use in controlling the phytopathogenic fungi or damaging insects of plants, crops or seeds at a site. The pesticide composition according to the invention can be prepared immediately before use by using a kit-of-parts for controlling, curatively or preventively, the phytopathogenic fungi of crops, such a kit-of-parts may comprise at least one or several compounds (A), (B), (C) and (D) intended to be combined or used simultaneously, separately or sequentially in controlling the phytopathogenic fungi of crops at a site. It is therefore a pack wherein the user finds all the ingredients for preparing the fungicide formulation which they wish to apply to the crops. These ingredients, which comprise in particular the active agents (A), (B), (C) and (D) and which are packaged separately, are provided in the form of a powder or in the form of a liquid which is concentrated to a greater or lesser degree. The user simply has to mix in the prescribed doses and to add the quantities of liquid, for example of water, necessary to obtain a formulation which is ready to use and which can be applied to the crops. The good fungicidal activity of the active compound combinations according to the invention is evident from the example below. While the individual active compounds exhibit weaknesses with regard to the fungicidal activity, the combinations have an activity which exceeds a simple addition of activities.
A synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
The expected activity for a given combination of two active compounds can be calculated as follows (cf. Colby, S. R., "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds 15, pages 20-22, 1967):
If
X is the efficacy, when applying the active compound A at a rate of application of active compound of m ppm,
Y is the efficacy, when applying the active compound B at a rate of application of active compound of n ppm,
E is the expected efficacy, when applying the active compounds A and B at rates of application of active compound of m and n ppm,
E = X+Y-^± then 100
The degree of efficacy, expressed in % is denoted. 0% means an efficacy which corresponds to that of the control while an efficacy of 100% means that no disease is observed.
If the actual fungicidal activity exceeds the calculated value, then the activity of the combination is superadditive, i.e. a synergistic effect exists. In this case, the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the abovementioned formula.
The invention is illustrated by the following examples. Example A : Phytophthora test (tomatoes) / protective
Solvent: 24,5 parts by weight of acetone
24,5 parts by weight of dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
To test for protective activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans. The plants are then placed in an incubation cabinet at approximately 2O0C and a relative atmospheric humidity of 100%.
The test is evaluated 3 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.
The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.
Table 1 : Phytophthora test (tomatoes) / protective
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
found = activity found calc. = activity calculated using Colby's formula Table 2: Phytophthora test (tomatoes) / protective
Figure imgf000047_0001
found = activity found calc. = activity calculated using Colby's formula Table 3: Phytophthora test (tomatoes) / protective
Figure imgf000048_0001
found = activity found calc. = activity calculated using Colby's formula
Table 4: Phytophthora test (tomatoes) / protective
Figure imgf000048_0002
found = activity found calc. = activity calculated using Colby's formula Table 5: Phytophthora test (tomatoes) / protective
Figure imgf000049_0001
found = activity found calc. = activity calculated using Colby's formula
Table 6: Phytophthora test (tomatoes) / protective
Figure imgf000049_0002
found = activity found calc. = activity calculated using Colby's formula
Example B: Sphaerotheca test (cucumbers) / protective
Solvent: 24,5 parts by weight of acetone
24,5 parts by weight of dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
To test for protect activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in a greenhouse at approximately 230C and a relative atmospheric humidity of approximately 70%.
The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.
The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.
Table 7: Sphaerotheca test (cucumbers) / protective
Figure imgf000050_0001
Ex. B9 prothioconazole 1 50
Ex. B9 tebuconazole 2 13
Ex. B9 triadimenol 1 38
Ex. B3 trifloxystrobin 2,5 58
A + B9 epoxiconazole 50:1 50 + 1 83 68
A + B9 fluquinconazole 50:1 25 + 0,5 88 68
A + B9 propiconazole 50:1 50 + 1 94 24
A + B9 prothioconazole 50:1 50 + 1 73 57
A + B9 tebuconazole 50:1 100 + 2 67 24
A + B9 triadimenol 50:1 50 + 1 83 46
A + B9 trifloxystrobin 10:1 25 + 2,5 90 63 found = activity found ** calc. = activity calculated using Colby's formula
Table 8: Sphaerotheca test (cucumbers) / protective
Figure imgf000051_0001
found = activity found ** calc. = activity calculated using Colby's formula Example C: Botrytis test (beans) / protective
Solvent: 24,5 parts by weight of acetone
24,5 parts by weight of dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
To test for protective activity, young plants are sprayed with the preparation of active compound. After the spray coating has dried on, 2 small pieces of agar covered with growth of Botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened chamber at 20oC and a relative atmospheric humidity of 100%.
2 days after the inoculation, the size of the lesions on the leaves is evaluated. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.
The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.
Table 9: Botrytis test (beans) / protective
Figure imgf000052_0001
Figure imgf000053_0001
found = activity found calc. = activity calculated using Colby's formula
Table 10: Botrytis test (beans) / protective
Figure imgf000053_0002
found = activity found calc. = activity calculated using Colby's formula Example D: Pythium test (cotton) / seed treatment
The test is performed under greenhouse conditions.
Cotton seeds, treated with the active compound or compound combinations, solved in N- methyl-2-pyrrolidon and diluted with water to the desired dosages, were sown in 6*6cm pots containing 4 cm of a 1 :1 mix of steamed field soil and sand.
Perlite was incubated with mycelium fragments of Pythium ultimum. 1 ml of infected perlite was scattered between the treated cotton seeds. Seeds were then covered by light expanded clay aggregate. Pots were incubated in the greenhouse 7 days at 2O0C and 80% relative humidity.
Assessment consisted of counting of emerged seedlings. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that all seedlings have emerged.
The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.
Table 11 : Pythium test (cotton) / seed treatment
Figure imgf000054_0001
A + B10 mandipropamid 1:100 0,1 + 10 61 30
A + B1 mefenoxam 1:1 0,1 +0,1 78 64
A + B1 benalaxyl-M 1:10 0,1 + 1 61 33
A + B3 fenamidone 1:10 0,1 + 1 52 33 found = activity found calc. = activity calculated using Colby's formula

Claims

1. A composition comprising:
A) a tetrazolyloxime derivative of formula (I)
Figure imgf000056_0001
(I) wherein
• R1 represents a hydrogen atom, a halogen atom, a substituted or non-substituted Ci-C6- alkyl, a substituted or non-substituted d-C6-alkoxy, nitro, cyano, a substituted or non- substituted d-C6-aryl or a substituted or non-substituted C-ι-C6-alkylsulphonyl;
• q represents 0,1 ,2, 3, 4 or 5;
• A represents a tetrazoyl group of formula (A1) or (A2):
Figure imgf000056_0002
(A1) (A2) wherein Y represents an d-C6-alkyl group ; and
• D represents a pyridyl group of formula (D1) or a thiazolyl group of formula (D2) ;
• D represents a pyridyl group of formula (D1) or a thiazolyl group of formula (D2) ;
Figure imgf000056_0003
wherein R2 and R3 independently represent a hydrogen atom, a halogen atom, a substituted or non-substituted C-ι-C8-alkyl, nitro, cyano, a hydroxy group, a mercapto group, formyl, hydroxycarbonyl, a substituted or non-substituted amino, a substituted or non-substituted C2-C8-alkenyl, a substituted or non-substituted C2-C8-alkynyl, a substituted or non-substituted aryl, a substituted or non-substituted heterocyclyl, ORa , S(O)rRa, C0Ra or CO2R3; wherein Ra represents a substituted or non-substituted CrC8- alkyl, a substituted or non-substituted amino, a substituted or non-substituted C3-C8- cycloalkyl, a substituted or non-substituted C2-C8-alkenyl, a substituted or non- substituted C2-C8-alkynyl, a substituted or non-substituted aryl; wherein r represents 0,
1 or 2; n represents 0, 1 , 2 or 3;
Provided that when n represents 0 or when R3 represents a hydrogen atom, Z represents Q1CONH- , wherein Q1 represents a substituted or non-substituted C1-C8- haloalkyl comprising between one and 9 halogen atoms, a substituted or non- substituted C2-C8-haloalkenyl comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkynyl, a substituted or non-substituted C2-C8- haloalkynyl comprising between one and 9 halogen atoms, a substituted or non- substituted d-C8-haloalkoxy comprising between one and 9 halogen atoms, , a substituted or non-substituted C2-C8-alkenyloxy, a substituted or non-substituted C2-C8- haloalkenyloxy comprising between one and 9 halogen atoms, a substituted or non- substituted C2-C8-alkynyloxy, a substituted or non-substituted C2-C8-haloalkynyloxy comprising between one and 9 halogen atoms, a Ci-C8-alkoxy substituted with a C1-C8- alkoxycarbonylamino, a d-C8-alkoxy substituted with a C3-C8-cycloalkyl, a branched Ci-C8-alkyl substituted with an aryl, a d-C8-alkoxy substituted with an aryl, a C1-C8- alkoxy substituted with a substituted or unsubstituted heterocyclyl, a d-C8-alkoxy substituted with a substituted or unsubstituted d-C8-alkoxy, a d-C8-alkoxy substituted with a substituted or unsubstituted aryloxy, a d-C8-alkoxy substituted with a substituted or unsubstituted aralkyloxy, a d-C8-alkoxy substituted with a substituted or unsubstituted d-C8-alkylthio, a d-C8-alkoxy substituted with a substituted or unsubstituted d-C8-arylthio, a d-C8-alkoxy substituted with a substituted or unsubstituted d-C8-alkylsulphinyl, a d-C8-alkoxy substituted with a substituted or unsubstituted arylsulphinyl, a d-C8-alkoxy substituted with a substituted or unsubstituted d-C8-alkylsulphony, a d-C8-alkoxy substituted with a substituted or unsubstituted arylsulphonyl, d-C8-alkoxy substituted with a substituted or unsubstituted d-C8-alkylamino, d-C8-alkoxy substituted with a substituted or unsubstituted aralkylamino, an aryloxy, d-C8-alkyl substituted with a carboxyl residue, d-C8-alkyl substituted with a substituted or unsubstituted aralkylamino, d-C8-alkyl substituted with a substituted or unsubstituted aryloxy, d-C8-alkyl substituted with an acyl group, C1-C8- alkyl substituted with a substituted or unsubstituted heterocyclyl group; Provided that when n represents 1 and R2represents a halogen atom, Z represents a hydrogen atom, an amino or Q2CONH-, wherein Q2 represents a hydrogen atom, a substituted or non-substituted Ci-C8-haloalkyl comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkenyl, a substituted or non-substituted C2-C8-haloalkenyl comprising between one and 9 halogen atoms, a substituted or non- substituted C2-C8-alkynyl, a substituted or non-substituted C2-C8-haloalkynyl comprising between one and 9 halogen atoms, a substituted or non-substituted Ci-C8-alkoxy, a substituted or non-substituted Ci-C8-haloalkoxy comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkenyloxy, a substituted or non- substituted C2-C8-haloalkenyloxy comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkynyloxy, a substituted or non-substituted C2-C8- haloalkynyloxy comprising between one and 9 halogen atoms, a substituted or unsubstituted C3-C8-cycloalkyl, a substituted or unsubstituted C3-C8-cycloalkoxy, a substituted or non-substituted d-C8-alkylamino, a d-C8-alkoxy substituted or non- substituted amino, a d-C8-alkoxy substituted with a C3-C8-cycloalkyl, a substituted or unsubstituted aralkyloxy, a d-C8-alkoxy substituted with a substituted or unsubstituted heterocyclyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8- alkoxy, a Ci-C8-alkoxy substituted with a substituted or unsubstituted aryloxy, a Ci-C8- alkoxy substituted with a substituted or unsubstituted aralkyloxy, C2-C8-alkynyloxy substituted with a substituted or unsubstituted aryl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylthio, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-arylthio, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylsulphinyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted arylsulphinyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylsulphony, a Ci-C8-alkoxy substituted with a substituted or unsubstituted arylsulphonyl, an aryloxy, Ci-C8-alkyl substituted with a carboxyl residue, Ci-C8-alkyl substituted with a substituted or unsubstituted amino, Ci-C8-alkyl substituted with a substituted or unsubstituted aryloxy, a Ci-C8-alkyl substituted with a substituted or unsubstituted Ci-C8-alkylthio, a Ci-C8-alkyl substituted with a substituted or unsubstituted Ci-C8-alkoxy, Ci-C8-alkyl substituted with an acyl group, Ci-C8-alkyl substituted with a substituted or unsubstituted heterocyclyl group; Provided that when R3 represents a halogen atom, Z represents a hydrogen atom, an amino or Q1CONH-, Q1 being herein-defined;
Provided that when n represents 2 or 3 and when R2 or R3 independently represents a hydroxy group, a mercapto group, a non-substituted Ci-C8-alkyl, nitro, cyano, formyl, hydroxycarbonyl, a substituted or non-substituted amino, a substituted or non- substituted C2-C8-alkenyl, a substituted or non-substituted C2-C8-alkynyl, a substituted or non-substituted aryl, a substituted or non-substituted heterocyclyl, ORa , S(O)rRa, C0Ra or CO2R3 , Ra being herein-defined or when n represents 3 and when R2 represents a halogen atom, Z represents a hydrogen atom, an amino or Q3CONH- , wherein Q3 represents a hydrogen atom, a substituted or non-substituted Ci-C8-alkyl, a substituted or non-substituted Ci-C8-haloalkyl comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkenyl, a substituted or non-substituted C2-C8-haloalkenyl comprising between one and 9 halogen atoms, a substituted or non- substituted C2-C8-alkynyl, a substituted or non-substituted C2-C8-haloalkynyl comprising between one and 9 halogen atoms, a substituted or non-substituted d-C8-alkoxy, a substituted or non-substituted d-C8-haloalkoxy comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkenyloxy, a substituted or non- substituted C2-C8-haloalkenyloxy comprising between one and 9 halogen atoms, a substituted or non-substituted C2-C8-alkynyloxy, a substituted or non-substituted C2-C8- haloalkynyloxy comprising between one and 9 halogen atoms, a substituted or unsubstituted C3-C8-cycloalkyl, a substituted or unsubstituted C3-C8-cycloalkoxy, a substituted or non-substituted Ci-C8-alkylamino, a Ci-C8-alkoxy substituted or non- substituted amino, a Ci-C8-alkoxy substituted with a C3-C8-cycloalkyl, a substituted or unsubstituted aralkyloxy, a Ci-C8-alkoxy substituted with a substituted or unsubstituted heterocyclyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8- alkoxy, a Ci-C8-alkoxy substituted with a substituted or unsubstituted aryloxy, a Ci-C8- alkoxy substituted with a substituted or unsubstituted aralkyloxy, C2-C8-alkynyloxy substituted with a substituted or unsubstituted aryl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylthio, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-arylthio, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylsulphinyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted arylsulphinyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted Ci-C8-alkylsulphonyl, a Ci-C8-alkoxy substituted with a substituted or unsubstituted arylsulphonyl, an aryloxy, Ci-C8-alkyl substituted with a carboxyl residue, Ci-C8-alkyl substituted with a substituted or unsubstituted amino, Ci-C8-alkyl substituted with a substituted or unsubstituted aryloxy, a Ci-C8-alkyl substituted with a substituted or unsubstituted Ci-C8-alkylthio, a Ci-C8-alkyl substituted with a substituted or unsubstituted Ci-C8-alkoxy, Ci-C8-alkyl substituted with an acyl group, Ci-C8-alkyl substituted with a substituted or unsubstituted heterocyclyl group; as well as salts, N-oxides, metallic complexes and metalloidic complexes thereof or (E) and (Z) isomers and mixtures thereof
and
B) a fungicide compound in an A/B weight ratio ranging from 0.001/1 to 1/1 ,000.
2. A composition comprising:
A) a tetrazolyloxime derivative of formula (I) wherein formula (I) is defined as in claim 1 ;
B) a fungicide compound and
C) a second further fungicide compound in an A/B/C weight ratio ranging from 0.001/0.001/1 to 1/1 ,000/1 ,000.
3. A composition comprising:
A) a tetrazolyloxime derivative of formula (I) wherein formula (I) is defined as in claim 1 ;
B) a fungicide compound and
D) an insecticide compound in an A/B/D weight ratio ranging from 0.001/0.001/1 to 1/1 ,000/1 ,000.
4. A composition comprising:
A) a tetrazolyloxime derivative of formula (I) wherein formula (I) is defined as in claim 1 and D) an insecticide compound in an A/D weight ratio ranging from 1/1 ,000 to 1 ,000/1.
5. A composition comprising:
A) a tetrazolyloxime derivative of formula (I) wherein formula (I) is defined as in claim 1 ;
B) a fungicide compound ; C) a second further fungicide compound and
D) an insecticide compound in an A/B/C/D weight ratio ranging from 0.001/0.001/0.001/1 to 1/1 ,000/1 ,000/1 ,000.
6. A composition according to claims 1 to 5 wherein the substitution position of R1 in the tetrazolyloxime derivative of formula (I) is not specifically limited and R1 represents a hydrogen atom, a halogen atom, a substituted or non-substituted d-C6-alkyl, a substituted or non-substituted d-C6-alkoxy.
7. A composition according to claims 1 to 6 wherein the substitution position of R1 in the tetrazolyloxime derivative of formula (I) is not specifically limited and R1 represents a hydrogen atom, a halogen atom, a methyl group, a tert-butyl group, a methoxy group or an ethoxy group.
8. A composition according to claim 7 wherein R1 represents a hydrogen atom or a halogen atom.
9. A composition according to claims 1 to 8 wherein Y represents a methyl group.
10. A composition according to claims 1 to 9 wherein R2 and R3 independently represent a hydrogen atom or a halogen atom.
11. A composition according to claims 1 to 10 wherein the tetrazolyloxime derivative of formula (1 ) is but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1 H-tetrazol-5-yl)(phenyl)methylene]- amino}oxy)methyl]pyridin-2-yl}carbamate.
12. A composition according to claims 1 , 2, 3, 5 to 11 wherein fungicide compounds B and C are independently selected in the list consisting of:
(1.1 ) aldimorph (1704-28-5), (1.2) azaconazole (60207-31-0), (1.3) bitertanol (55179-
31-2), (1.4) bromuconazole (116255-48-2), (1.5) cyproconazole (1 13096-99-4), (1.6) diclobutrazole (75736-33-3), (1.7) difenoconazole (1 19446-68-3), (1.8) diniconazole
(83657-24-3), (1.9) diniconazole-M (83657-18-5), (1.10) dodemorph (1593-77-7), (1.11 ) dodemorph acetate (31717-87-0), (1.12) epoxiconazole (106325-08-0), (1.13) etaconazole (60207-93-4), (1.14) fenarimol (60168-88-9), (1.15) fenbuconazole (114369-43-6), (1.16) fenhexamid (126833-17-8), (1.17) fenpropidin (67306-00-7), (1.18) fenpropimorph (67306-03-0), (1.19) fluquinconazole (136426-54-5), (1.20) flurprimidol (56425-91-3), (1.21 ) flusilazole (85509-19-9), (1.22) flutriafol (76674-21-0), (1.23) furconazole (112839-33-5), (1.24) furconazole-cis (112839-32-4), (1.25) hexaconazole (79983-71-4), (1.26) imazalil (60534-80-7), (1.27) imazalil sulfate (58594- 72-2), (1.28) imibenconazole (86598-92-7), (1.29) ipconazole (125225-28-7), (1.30) metconazole (125116-23-6), (1.31 ) myclobutanil (88671-89-0), (1.32) naftifine (65472- 88-0), (1.33) nuarimol (63284-71-9), (1.34) oxpoconazole (174212-12-5), (1.35) paclobutrazol (76738-62-0), (1.36) pefurazoate (101903-30-4), (1.37) penconazole (66246-88-6), (1.38) piperalin (3478-94-2), (1.39) prochloraz (67747-09-5), (1.40) propiconazole (60207-90-1 ), (1.41 ) prothioconazole (178928-70-6), (1.42) pyributicarb (88678-67-5), (1.43) pyrifenox (88283-41-4), (1.44) quinconazole (103970-75-8), (1.45) simeconazole (149508-90-7), (1.46) spiroxamine (118134-30-8), (1.47) tebuconazole (107534-96-3), (1.48) terbinafine (91 161-71-6), (1.49) tetraconazole (112281-77-3), (1.50) triadimefon (43121-43-3), (1.51 ) triadimenol (89482-17-7), (1.52) tridemorph (81412-43-3), (1.53) triflumizole (68694-11-1 ), (1.54) triforine (26644-46-2), (1.55) triticonazole (131983-72-7), (1.56) uniconazole (83657-22-1 ), (1.57) uniconazole-p
(100761-65-7), (1.58) viniconazole (77174-66-4), (1.59) voriconazole (137234-62-9), (1.60) i^-chlorophenyO^I H-i ^^-triazol-i-yOcycloheptanol (129586-32-9), (1.61 ) methyl 1-(2,2-dimethyl-2,3-dihydro-1 H-inden-1-yl)-1 H-imidazole-5-carboxylate (11 1323- 95-0), (1.62) N'-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl- N-methylimidoformamide, (1.63) N-ethyl-N-methyl-N'-{2-methyl-5-(trifluoronnethyl)-4-[3-
(trimethylsilyl)propoxy]phenyl}imidoformannide and (1.64) O-{1-[(4- methoxyphenoxy)methyl]-2,2-dimethylpropyl} I H-imidazole-1-carbothioate (11 1226-71-
2),
(2.1 ) bixafen (581809-46-03), (2.2) boscalid (188425-85-6), (2.3) carboxin (5234-68-4), (2.4) diflumetorim (130339-07-0), (2.5) fenfuram (24691-80-3), (2.6) fluopyram (658066-
35-4), (2.7) flutolanil (66332-96-5), (2.8) furametpyr (123572-88-3), (2.9) furmecyclox (60568-05-0), (2.10) isopyrazam (mixture of syn-epimeric racemate 1 RS, 4SR, 9RS and anti-epimeric racemate 1 RS,4SR,9SR) (881685-58-1 ), (2.11 ) isopyrazam (anti-epimeric racemate 1 RS, 4SR, 9SR), (2.12) isopyrazam (anti-epimeric enantiomer 1 R,4S,9S), (2.13) isopyrazam (anti-epimeric enantiomer 1 S,4R,9R), (2.14) isopyrazam (syn epimeric racemate 1 RS, 4SR, 9RS), (2.15) isopyrazam (syn-epimeric enantiomer 1 R,4S,9R), (2.16) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.17) mepronil (55814-41-0), (2.18) oxycarboxin (5259-88-1 ), (2.19) penflufen (494793-67-8), (2.20) penthiopyrad (183675-82-3), (2.21 ) sedaxane (874967-67-6), (2.22) thifluzamide (130000-40-7), (2.23) 1-methyl-N-[2-( 1 ,1 ,2, 2-tetraf luoroethoxy)phenyl]-3-
(trifluoromethyl)-1 H-pyrazole-4-carboxamide, (2.24) 3-(difluoromethyl)-1-methyl-N- (3',4',5'-trifluorobiphenyl-2-yl)-1 H-pyrazole-4-carboxamide, (2.25) 3-(difluoromethyl)-1- methyl-N-[2-(1 ,1 ,2,2-tetrafluoroethoxy)phenyl]-1 H-pyrazole-4-carboxamide, (2.26) 3- (difluoromethyl)-N-[4-fluoro-2-(1 ,1 ,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1 H- pyrazole-4-carboxamide, (3.1 ) amisulbrom (348635-87-0), (3.2) azoxystrobin (131860-33-8), (3.3) cyazofamid (120116-88-3), (3.4) dimoxystrobin (141600-52-4), (3.5) enestroburin (238410-11-2), (3.6) famoxadone (131807-57-3), (3.7) fenamidone (161326-34-7), (3.8) fluoxastrobin (361377- 29-9), (3.9) kresoxim-methyl (143390-89-0), (3.10) metominostrobin (133408-50-1 ), (3.11 ) orysastrobin (189892-69-1 ), (3.12) picoxystrobin (117428-22-5), (3.13) pyraclostrobin
(175013-18-0), (3.14) pyrametostrobin (915410-70-7), (3.15) pyraoxystrobin (862588-11- 2), (3.16) pyribencarb (799247-52-2), (3.17) trifloxystrobin (141517-21-7), (3.18) (2E)-2-(2- {[6-(3-chloro-2-methylphenoxy)-5-fluoropyrinnidin-4-yl]oxy}phenyl)-2-(nnethoxyinnino)-N- methylethanamide, (3.19) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1 E)-1-[3- (trifluoromethyl)phenyl]ethylidene}annino)oxy]nnethyl}phenyl)ethanannide, (3.20) (2E)-2-
(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-
(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide (158169-73-4), (3.21 ) (2E)- 2-{2-[({[(1 E)-1-(3-{[(E)-1-fluoro-2- phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)nnethyl]phenyl}-2-(nnethoxyinnino)-N- methylethanamide (326896-28-0), (3.22) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3- en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide, (3.23) 2- chloro-N-(1 ,1 ,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)pyridine-3-carboxamide (119899-14-8), (3.24) 5-methoxy-2-methyl-4-(2-{[({(1 E)-1-[3- (trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1 ,2,4-triazol-3- one, (3.25) methyl 2-{2-[({cyclopropyl[(4- methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3-methoxyacrylate (149601-03-6),
(3.26) N^S-ethyl-S.S.S-trimethylcyclohexyO-S^formylamino^-hydroxybenzamide (226551-
21-9),
(4.1 ) benomyl (17804-35-2), (4.2) carbendazim (10605-21-7), (4.3) chlorfenazole (3574-96- 7), (4.4) diethofencarb (87130-20-9), (4.5) ethaboxam (162650-77-3), (4.6) fluopicolide
(239110-15-7), (4.7) fuberidazole (3878-19-1 ), (4.8) pencycuron (66063-05-6), (4.9) thiabendazole (148-79-8), (4.10) thiophanate-methyl (23564-05-8), (4.11 ) thiophanate (23564-06-9), (4.12) zoxamide (156052-68-5) and (4.13) 5-chloro-7-(4-methylpiperidin-1- yl)-6-(2,4,6-trifluorophenyl)[1 ,2,4]triazolo[1 ,5-a]pyrimidine (214706-53-3), (5.1 ) bordeaux mixture (8011-63-0), (5.2) captafol (2425-06-1 ), (5.3) captan (133-06-2), (5.4) chlorothalonil (1897-45-6), (5.5) copper hydroxide (20427-59-2), (5.6) copper naphthenate (1338-02-9), (5.7) copper oxide (1317-39-1 ), (5.8) copper oxychloride (1332-40-7), (5.9) copper(2+) sulfate (7758-98-7), (5.10) dichlofluanid (1085-98-9), (5.11 ) dithianon (3347-22- 6), (5.12) dodine (2439-10-3), (5.13) dodine free base, (5.14) ferbam (14484-64-1 ), (5.15) fluorofolpet (719-96-0), (5.16) folpet (133-07-3), (5.17) guazatine (108173-90-6), (5.18) guazatine acetate, (5.19) iminoctadine (13516-27-3), (5.20) iminoctadine albesilate (169202- 06-6), (5.21 ) iminoctadine triacetate (57520-17-9), (5.22) mancopper (53988-93-5), (5.23) mancozeb (2234562), (5.24) maneb (12427-38-2), (5.25) metiram (9006-42-2), (5.26) metiram zinc (9006-42-2), (5.27) oxine-copper (10380-28-6), (5.28) propamidine (104-32-5), (5.29) propineb (12071-83-9), (5.30) sulphur and sulphur preparations including calcium polysulphide (7704-34-9), (5.31 ) thiram (137-26-8), (5.32) tolylfluanid (731-27-1 ), (5.33) zineb (12122-67-7), (5.34) ziram (137-30-4),
(6.1 ) acibenzolar-S-methyl (135158-54-2), (6.2) isotianil (224049-04-1 ), (6.3) probenazole (27605-76-1 ), (6.4) tiadinil (223580-51-6), (7.1 ) andoprim (23951-85-1 ), (7.2) blasticidin-S (2079-00-7), (7.3) cyprodinil (121552-61-2),
(7.4) kasugamycin (6980-18-3), (7.5) kasugamycin hydrochloride hydrate (19408-46-9), (7.6) mepanipyrim (110235-47-7), (7.7) pyrimethanil (53112-28-0),
(8.1 ) fentin acetate (900-95-8), (8.2) fentin chloride (639-58-7), (8.3) fentin hydroxide (76-87- 9), (8.4), silthiofam (175217-20-6), (9.1 ) benthiavalicarb (177406-68-7), (9.2) dimethomorph (110488-70-5), (9.3) flumorph
(211867-47-9), (9.4) iprovalicarb (140923-17-7), (9.5) mandipropamid (374726-62-2), (9.6) polyoxins (11 113-80-7), (9.7) polyoxorim (22976-86-9), (9.8) validamycin A (37248-47-8), (9.9) valifenalate (283159-94-4; 283159-90-0), (10.1 ) biphenyl (92-52-4), (10.2) chloroneb (2675-77-6), (10.3) dicloran (99-30-9), (10.4) edifenphos (17109-49-8), (10.5) etridiazole (2593-15-9), (10.6) iodocarb (55406-53-6), (10.7) iprobenfos (26087-47-8), (10.8) isoprothiolane (50512-35-1 ), (10.9) propamocarb (25606-41- 1 ), (10.10) propamocarb hydrochloride (25606-41-1 ), (10.11 ) prothiocarb (19622-08-3), (10.12) pyrazophos (13457-18-6), (10.13) quintozene (82-68-8), (10.14) tecnazene (117-18- 0), (10.15) tolclofos-m ethyl (57018-04-9), (11.1 ) carpropamid (104030-54-8), (11.2) diclocymet (139920-32-4), (11.3) fenoxanil (115852-48-7), (11.4) phthalide (27355-22-2),
(11.5) pyroquilon (57369-32-1 ), (11.6) tricyclazole (41814-78-2),
(12.1 ) benalaxyl (71626-11-4), (12.2) benalaxyl-M (98243-83-5), (12.3) bupirimate (41483- 43-6), (12.4) clozylacon (67932-85-8), (12.5) dimethirimol (5221-53-4), (12.6) ethirimol (23947-60-6), (12.7) furalaxyl (57646-30-7), (12.8) hymexazol (10004-44-1 ), (12.9) metalaxyl (57837-19-1 ), (12.10) metalaxyl-M (70630-17-0), (12.11 ) ofurace (58810-48-3), (12.12) oxadixyl (77732-09-3), (12.13) oxolinic acid (14698-29-4),
(13.1 ) chlozolinate (84332-86-5), (13.2) fenpiclonil (74738-17-3), (13.3) fludioxonil (131341- 86-1 ), (13.4) iprodione (36734-19-7), (13.5) procymidone (32809-16-8), (13.6) quinoxyfen (124495-18-7), (13.7) vinclozolin (50471-44-8), (14.1 ) binapacryl (485-31-4), (14.2) dinocap (131-72-6), (14.3) ferimzone (89269-64-7), (14.4) fluazinam (79622-59-6), (14.5) meptyldinocap (131-72-6), (15.1 ) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1 ,2-oxazol-3-yl]-1 ,3-thiazol-2- yl}piperidin-1-yl)-2-[5-nnethyl-3-(trifluoronnethyl)-1 H-pyrazol-1-yl]ethanone, (15.2) 1-[(4- methoxyphenoxy)methyl]-2,2-dimethylpropyl I H-imidazole-1-carboxylate (11 1227-17-9),
(15.3) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine (13108-52-6), (15.4) 2,3-dibutyl-6- chlorothieno[2,3-d]pyrimidin-4(3H)-one (221451-58-7), (15.5) 2-[5-methyl-3-(trifluoromethyl)- 1 H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1 ,2-oxazol-3-yl]-1 ,3-thiazol-2-yl}piperidin- 1-yl)ethanone, (15.6) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.7) 2-phenylphenol and salts (90-43-7), (15.8) 3,4,5-trichloropyridine-2,6-dicarbonitrile (17824-85-0), (15.9) 3-[5-
(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine, (15.10) 3-chloro-5-(4-chlorophenyl)- 4-(2,6-difluorophenyl)-6-methylpyridazine, (15.11 ) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)- 3,6-dimethylpyridazine, (15.12) 5-amino-1 ,3,4-thiadiazole-2-thiol, (15.13) 5-chloro-N'-phenyl- N'-prop-2-yn-1-ylthiophene-2-sulfonohydrazide (134-31-6), (15.14) 5-methyl-6-octyl-3,7- dihydro[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-amine, (15.15) ametoctradin (865318-97-4), (15.16) benthiazole (21564-17-0), (15.17) bethoxazin (163269-30-5), (15.18) capsimycin (70694-08- 5), (15.19) carvone (99-49-0), (15.20) chinomethionat (2439-01-2), (15.21 ) chlazafenone (688046-61-9), (15.22) cufraneb (11096-18-7), (15.23) cyflufenamid (180409-60-3), (15.24) cymoxanil (57966-95-7), (15.25) cyprosulfamide (221667-31-8), (15.26) dazomet (533-74-4), (15.27) debacarb (62732-91-6), (15.28) dichlorophen (97-23-4), (15.29) diclomezine (62865-
36-5), (15.30) difenzoquat (43222-48-6), (15.31 ) difenzoquat methylsulphate (43222-48-6), (15.32) diphenylamine (122-39-4), (15.33) ecomate, (15.34) ethyl (2Z)-3-amino-2-cyano-3- phenylprop-2-enoate, (15.35) flumetover (154025-04-4), (15.36) fluoroimide (41205-21-4), (15.37) flusulfamide (106917-52-6), (15.38) flutianil (304900-25-2), (15.39) fosetyl-aluminium (39148-24-8), (15.40) fosetyl-calcium, (15.41 ) fosetyl-sodium (39148-16-8), (15.42) hexachlorobenzene (118-74-1 ), (15.43) irumamycin (81604-73-1 ), (15.44) methasulfocarb (66952-49-6), (15.45) methyl isothiocyanate (556-61-6), (15.46) metrafenone (220899-03-6), (15.47) mildiomycin (67527-71-3), (15.48) N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1- yloxy)phenyl]propanamide, (15.49) N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop- 2-yn-1-yloxy)phenyl]propanamide, (15.50) N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4- dichloropyridine-3-carboxamide, (15.51 ) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4- dichloropyridine-3-carboxamide, (15.52) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4- iodopyridine-3-carboxamide, (15.53) N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)- 2,3-difluorophenyl]methyl}-2-phenylacetamide, (15.54) N-{(Z)-[(cyclopropylmethoxy)imino][6- (difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide (221201-92-9), (15.55) natamycin (7681-93-8), (15.56) nickel dimethyldithiocarbamate (15521-65-0), (15.57) nitrothal-isopropyl (10552-74-6), (15.58) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1 H- pyrazol-i-yllacetylJpiperidin^-yO-N^I ^.S^-tetrahydronaphthalen-i-yO-I .S-thiazole^- carboxamide, (15.59) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1- yl]acetyl}piperidin-4-yl)-N-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1-yl]-1 ,3-thiazole-4- carboxamide, (15.60) octhilinone (26530-20-1 ), (15.61 ) oxamocarb (917242-12-7), (15.62) oxyfenthiin (34407-87-9), (15.63) pentachlorophenol and salts (87-86-5), (15.64) pentyl {6- [({[(1-methyl-1 H-tetrazol-5-yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.65) phenazine-1-carboxylic acid, (15.66) phenothrin, (15.67) phosphorous acid and its salts (13598-36-2), (15.68) propamocarb-fosetylate, (15.69) propanosine-sodium (88498-02-
6), (15.70) proquinazid (189278-12-4), (15.71 ) pyrrolnitrine (1018-71-9), (15.72) quinolin-8-ol (134-31-6), (15.73) quinolin-8-ol sulfate (2:1 ) (salt) (134-31-6), (15.74) fenpyrazamine (473798-59-3), (15.75) tebufloquin (376645-78-2), (15.76) tecloftalam (76280-91-6), (15.77) tolnifanide (304911-98-6), (15.78) triazoxide (72459-58-6), (15.79) trichlamide (70193-21-4), (15.80) zarilamid (84527-51-5) and salts thereof.
13. A composition according to claim 12 wherein fungicide compounds B and C are independently selected in the list consisting of: ametoctradin, azoxystrobin, benalaxyl-M, benthiavalicarb, bixafen also known as N-(3',4'- dichloro-5-fluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1 H-pyrazole-4-carboxamide, boscalid, chlorothalonil, copper hydroxide, copper oxychloride, cyazofamid, cymoxanil, dimethomorph, epoxiconazole, famoxadone, fenamidone, fenhexamid, fluazinam, fludioxonil, fluopicolide, fluopyram also known as N-{2-[3-chloro-5-
(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide, fluoxastrobin, fluquinconazole, folpet, fosetyl-aluminium, iprodione, iprovalicarb, isopyrazam, mancozeb, mandipropamid, mefenoxam, metiram, penflufen, penthiopyrad, prochloraz, phosphorous acid, propamocarb, propamocarb-fosetylate, propamocarb hydrochloride, propiconazole, propineb, prothioconazole, pyraclostrobin, pyrimethanil, sedaxane, tebuconazole, triadimenol, trifloxystrobin, zoxamide, N-methyl-2-(1-{[5-methyl-3- (trifluoromethyl)-1 H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1 R)-1 ,2,3,4- tetrahydronaphthalen-1-yl]-1 ,3-thiazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N- (3',4',5'-trifluorobiphenyl-2-yl)-1 H-pyrazole-4-carboxamide and N-[2-(1 ,3-dimethyl-butyl)- phenyl]-5-fluoro-1 ,3-dimethyl-1 H-pyrazole-4-carboxamide.
14. A composition according to claims 3 to 13 wherein insecticide compound D is selected in the list consisting of:
(D1 ) carbamates, e.g. alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilan, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb; organophosphates, e.g. acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos- ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphon, dialifos, diazinon, dichlofenthion, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosmethilan, fosthiazate, heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl, O- salicylate, isoxathion, malathion, mecarbam, methacrifos, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion (-methyl/- ethyl), phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl/-ethyl), profenofos, propaphos, propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, vamidothion, and imicyafos, (D2) organochlorines, e.g. camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, and methoxychlor; fiproles (phenylpyrazoles), e.g. acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole,
(D3) pyrethroids, e.g. acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, deltamethrin, empenthrin (1 R isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis-, trans-), phenothrin (1 R trans isomer), prallethrin, profluthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau- fluvalinate, tefluthrin, terallethrin, tetramethrin (-1 R- isomer), tralomethrin, transfluthrin,
ZXI 8901 , pyrethrin (pyrethrum), eflusilanat;
DDT; or methoxychlor, (D4) chloronicotinyls, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, imidaclothiz, nitenpyram, nithiazine, thiacloprid, thiamethoxam, AKD-1022, nicotine, bensultap, cartap, thiosultap-sodium, thiocylam,
(D5) spinosyns, e.g. spinosad and spinetoram;
(D6) mectins/macrolides, e.g. abamectin, emamectin, emamectin benzoate, ivermectin, lepimectin, and milbemectin; juvenile hormone analogues, e.g. hydroprene, kinoprene, methoprene, epofenonane, triprene, fenoxycarb, pyriproxifen, diofenolan,
(D7) gassing agents, e.g. methyl bromide, chloropicrin and sulfuryl fluoride; selective antifeedants, e.g. cryolite, pymetrozine, pyrifluquinazon and flonicamid; or mite growth inhibitors, e.g. clofentezine, hexythiazox, etoxazole,
(D8) diafenthiuron; organotin compounds, e.g. azocyclotin, cyhexatin, fenbutatin oxide; propargite, tetradifon;
(D9) chlorfenapyr, binapacryl, dinobuton, dinocap, DNOC,
(D10) Bacillus thuringiensis strains, (D11 ) benzoylureas, e.g. bistrifluron, chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron,
(D12) Buprofezin,
(D13) cyromazine, (D14) diacylhydrazines, e.g. chromafenozide, halofenozide, methoxyfenozide, tebufenozide, and Fufenozide (JS118); azadirachtin,
(D15) amitraz,
(D16) hydramethylnon; acequinocyl; fluacrypyrim; cyflumetofen, cyenopyrafen,
(D17) fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone;. Indoxacarb, metaflumizone,
(D18) tetronic acid derivatives, e.g. spirodiclofen and spiromesifen; tetramic acid derivatives, e.g. spirotetramat,
(D 19) bifenazate,
(D20) diamides, e.g. flubendiamide, (R),(S)-3-chloro-N1-{2-methyl-4-[1 ,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulphonylethyl)phthalamide, chlorantraniliprole (Rynaxypyr), Cyantraniliprole (Cyazypyr), (D21 ) amidoflumet, benclothiaz, benzoximate, bromopropylate, buprofezin, chinomethionat, chlordimeform, chlorobenzilate, clothiazoben, cycloprene, dicofol, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, flufenerim, flutenzin, gossyplure, japonilure, metoxadiazone, petroleum, potassium oleate, pyridalyl, sulfluramid, tetrasul, triarathene, verbutine;
4-{[(6-brompyrid-3-yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (known from WO 2007/115644), 4-{[(6-fluorpyrid-3-yl)methyl](2,2-difluorethyl)amino}furan-2(5H)-on (known from WO 2007/115644), 4-{[(2-chlor-1 ,3-thiazol-5-yl)methyl](2-fluorethyl)amino}furan- 2(5H)-on (known from WO 2007/115644), 4-{[(6-chlorpyrid-3-yl)methyl](2- fluorethyl)amino}furan-2(5H)-on (known from WO 2007/ 115644), 4-{[(6-chlorpyrid-3- yl)methyl](2,2-difluorethyl)amino}furan-2(5H)-on known from WO 2007/115644), 4-{[(6- chlor-5-fluorpyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (known from WO 2007/115643), 4-{[(5,6-dichlorpyrid-3-yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (known from WO 2007/115646), 4-{[(6-chlor-5-fluorpyrid-3-yl)methyl](cyclopropyl)amino}furan- 2(5H)-on (known from WO 2007/1 15643), 4-{[(6-chlorpyrid-3- yl)methyl](cyclopropyl)amino}furan-2(5H)-on (known from EP-A-O 539 588), 4-{[(6- chlorpyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (known from EP-A-O 539 588), [(6- chlorpyridin-3-yl)methyl](methyl)oxido-λ4-sulfanylidencyanamid, [1-(6-chlorpyridin-3- yl)ethyl](methyl)oxido-λ4-sulfanylidencyanamid and its diastereomeres (A) and (B)
Figure imgf000069_0001
(A) (B)
, [(6-trifluormethylpyridin-3-yl)methyl](methyl)oxido-λ4-sulfanylidencyanamid, or [1-(6- trifluormethylpyridin-3-yl)ethyl](methyl)oxido-λ4-sulfanylidencyanamid and its diastereomeres (C) and (D), namely Sulfoxaflor
Figure imgf000070_0001
(C) (D).
15. A method for controlling the phytopathogenic fungi or damaging insects of plants, crops or seeds comprising the application of an agronomically effective and substantially non- phytotoxic quantity of a pesticide composition according to claims 1 to 14 as seed treatment, foliar application, stem application, drench or drip application or chemigation to the seed, the plant or to the fruit of the plant or to soil or to inert substrate, Pumice, Pyroclastic materials or stuff, synthetic organic substrates organic substrates or to a liquid substrate wherein the plant is growing or wherein it is desired to grow.
PCT/EP2010/052018 2009-02-19 2010-02-18 Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance WO2010094728A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2011550559A JP2012518028A (en) 2009-02-19 2010-02-18 Pesticide composition comprising a tetrazolyloxime derivative and a fungicide active substance or insecticide active substance
EP10706189A EP2398326A1 (en) 2009-02-19 2010-02-18 Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance
US13/202,200 US20120027741A1 (en) 2009-02-19 2010-02-18 Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP09356013 2009-02-19
EP09356013.4 2009-02-19

Publications (1)

Publication Number Publication Date
WO2010094728A1 true WO2010094728A1 (en) 2010-08-26

Family

ID=40853866

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2010/052018 WO2010094728A1 (en) 2009-02-19 2010-02-18 Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance

Country Status (6)

Country Link
US (1) US20120027741A1 (en)
EP (1) EP2398326A1 (en)
JP (1) JP2012518028A (en)
AR (1) AR075698A1 (en)
TW (1) TW201031331A (en)
WO (1) WO2010094728A1 (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102037969A (en) * 2011-01-12 2011-05-04 陕西美邦农药有限公司 Sterilization composition containing imibenconazole and methoxyl acrylate compound
WO2012045798A1 (en) 2010-10-07 2012-04-12 Bayer Cropscience Ag Fungicide composition comprising a tetrazolyloxime derivative and a thiazolylpiperidine derivative
WO2012088645A1 (en) * 2010-12-31 2012-07-05 Bayer Cropscience Ag Method for improving plant quality
CN103583522A (en) * 2012-08-17 2014-02-19 陕西美邦农药有限公司 Bactericidal composition containing fenarimol and strobilurin
CN103641795A (en) * 2013-04-18 2014-03-19 南开大学 Acetophenone derivatives containing 1,2,3-thiadiazole and preparation method and use thereof
CN103651428A (en) * 2011-05-17 2014-03-26 陕西韦尔奇作物保护有限公司 Insecticidal composition containing furan tebufenozide and antibiotic compound
CN104470364A (en) * 2012-05-01 2015-03-25 帝斯曼知识产权资产管理有限公司 Antifungal compositions
CN104502510A (en) * 2014-12-30 2015-04-08 山东出入境检验检疫局检验检疫技术中心 GC-NCI-MS (Gas Chromatography-Negative Chemical Ionization-Mass Spectrum) detecting method for residual quantity of cyenopyrafen in fruits and vegetables
EP2921491A1 (en) * 2011-12-27 2015-09-23 Bayer Intellectual Property GmbH Intermediates for the production of heteroarylpiperidine and heteroarylpiperazine derivatives as fungicides
WO2015141867A1 (en) 2014-03-20 2015-09-24 Mitsui Chemicals Agro, Inc. Plant disease control composition and method for controlling plant disease by application of same
WO2021153748A1 (en) 2020-01-29 2021-08-05 日本曹達株式会社 Agricultural and horticultural composition

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009119072A1 (en) * 2008-03-24 2009-10-01 日本曹達株式会社 Plant disease control agent
JP5512794B2 (en) * 2010-03-16 2014-06-04 日本曹達株式会社 Plant disease control agent
CN103271036B (en) * 2012-05-31 2014-04-09 陕西上格之路生物科学有限公司 Sterilization composition containing SYP-1620
CN103271076B (en) * 2012-05-31 2014-04-09 陕西上格之路生物科学有限公司 Bactericide composition containing SYP-1620
CN103271032B (en) * 2012-05-31 2014-04-09 陕西上格之路生物科学有限公司 Bactericide composition containing SYP-1620
US10709491B2 (en) 2013-08-06 2020-07-14 Memorial Sloan-Kettering Cancer Center System, method and computer-accessible medium for in-vivo tissue ablation and/or damage
CN105638667B (en) * 2015-12-29 2018-04-20 南京华洲药业有限公司 A kind of Synergistic insecticidal compositions and its application containing propargite and ethyl spinosad
CN106106496A (en) * 2016-06-24 2016-11-16 江苏省绿盾植保农药实验有限公司 Rice Suspension seed coat agent containing imidaclothiz and Rynaxypyr and application thereof
CN106689161A (en) * 2016-12-20 2017-05-24 东莞市瑞德丰生物科技有限公司 Picarbutrazox-containing bactericidal composition
WO2018140458A1 (en) 2017-01-24 2018-08-02 Germains Seed Technology, Inc. Anti-fungal seed treatment formulations, treated seeds, and methods

Citations (183)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4761373A (en) 1984-03-06 1988-08-02 Molecular Genetics, Inc. Herbicide resistance in plants
WO1989010396A1 (en) 1988-04-28 1989-11-02 Plant Genetic Systems N.V. Plants with modified stamen cells
WO1991002069A1 (en) 1989-08-10 1991-02-21 Plant Genetic Systems N.V. Plants with modified flowers
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5084082A (en) 1988-09-22 1992-01-28 E. I. Du Pont De Nemours And Company Soybean plants with dominant selectable trait for herbicide resistance
WO1992005251A1 (en) 1990-09-21 1992-04-02 Institut National De La Recherche Agronomique Dna sequence imparting cytoplasmic male sterility, mitochondrial genome, nuclear genome, mitochondria and plant containing said sequence and process for the preparation of hybrids
US5198599A (en) 1990-06-05 1993-03-30 Idaho Resarch Foundation, Inc. Sulfonylurea herbicide resistance in plants
EP0539588A1 (en) 1990-07-05 1993-05-05 Nippon Soda Co., Ltd. Amine derivative
EP0571427A1 (en) 1991-02-13 1993-12-01 Hoechst Schering AgrEvo GmbH Plasmids containing dna-sequences that cause changes in the carbohydrate concentration and the carbohydrate composition in plants, as well as plant cells and plants containing these plasmids
US5273894A (en) 1986-08-23 1993-12-28 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5276268A (en) 1986-08-23 1994-01-04 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
WO1994004693A2 (en) 1992-08-26 1994-03-03 Zeneca Limited Novel plants and processes for obtaining them
US5304732A (en) 1984-03-06 1994-04-19 Mgi Pharma, Inc. Herbicide resistance in plants
WO1994009144A1 (en) 1992-10-14 1994-04-28 Zeneca Limited Novel plants and processes for obtaining them
WO1994011520A2 (en) 1992-11-09 1994-05-26 Zeneca Limited Novel plants and processes for obtaining them
US5331107A (en) 1984-03-06 1994-07-19 Mgi Pharma, Inc. Herbicide resistance in plants
EP0607730A1 (en) 1992-12-24 1994-07-27 International Business Machines Corporation Method of direct transferring of electrically conductive elements into a substrate
EP0609022A2 (en) 1993-01-25 1994-08-03 Matsushita Electric Industrial Co., Ltd. Image encoding apparatus
EP0609013A2 (en) 1993-01-21 1994-08-03 Matsushita Electric Industrial Co., Ltd. Recording and reproducing apparatus
WO1994021795A1 (en) 1993-03-25 1994-09-29 Ciba-Geigy Ag Novel pesticidal proteins and strains
US5378824A (en) 1986-08-26 1995-01-03 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
WO1995004826A1 (en) 1993-08-09 1995-02-16 Institut Für Genbiologische Forschung Berlin Gmbh Debranching enzymes and dna sequences coding them, suitable for changing the degree of branching of amylopectin starch in plants
WO1995009910A1 (en) 1993-10-01 1995-04-13 Mitsubishi Corporation Gene that identifies sterile plant cytoplasm and process for preparing hybrid plant by using the same
US5434283A (en) 1990-04-04 1995-07-18 Pioneer Hi-Bred International, Inc. Edible endogenous vegetable oil extracted from rapeseeds of reduced stearic and palmitic saturated fatty acid content
EP0663956A1 (en) 1992-08-12 1995-07-26 Hoechst Schering AgrEvo GmbH Dna sequences which lead to the formation of polyfructans (levans), plasmids containing these sequences as well as a process for preparing transgenic plants
WO1995026407A1 (en) 1994-03-25 1995-10-05 National Starch And Chemical Investment Holding Corporation Method for producing altered starch from potato plants
US5463175A (en) 1990-06-25 1995-10-31 Monsanto Company Glyphosate tolerant plants
WO1995031553A1 (en) 1994-05-18 1995-11-23 Institut Für Genbiologische Forschung Berlin Gmbh DNA SEQUENCES CODING FOR ENZYMES CAPABLE OF FACILITATING THE SYNTHESIS OF LINEAR α-1,4 GLUCANS IN PLANTS, FUNGI AND MICROORGANISMS
WO1995035026A1 (en) 1994-06-21 1995-12-28 Zeneca Limited Novel plants and processes for obtaining them
WO1996001904A1 (en) 1994-07-08 1996-01-25 Stichting Scheikundig Onderzoek In Nederland Production of oligosaccharides in transgenic plants
EP0709000A1 (en) 1993-07-15 1996-05-01 Siemens Ag Method and device for firing an m-pulse d.c./a.c. converter assembly consisting of a master d.c./a.c. converter and at least one slave d.c./a.c. converter
WO1996015248A1 (en) 1994-11-10 1996-05-23 Hoechst Schering Agrevo Gmbh Dna molecules that code for enzymes involved in starch synthesis, vectors, bacteria, transgenic plant cells and plants containing said molecules
WO1996019581A1 (en) 1994-12-22 1996-06-27 Hoechst Schering Agrevo Gmbh Dna molecules coding for debranching enzymes derived from plants
EP0719338A1 (en) 1993-09-09 1996-07-03 Hoechst Schering AgrEvo GmbH Combination of dna sequences which enable the formation of modified starch in plant cells and plants, processes for the production of these plants and the modified starch obtainable therefrom
WO1996021023A1 (en) 1995-01-06 1996-07-11 Centrum Voor Plantenveredelings- En Reproduktieonderzoek (Cpro - Dlo) Dna sequences encoding carbohydrate polymer synthesizing enzymes and method for producing transgenic plants
EP0728213A1 (en) 1993-11-09 1996-08-28 E.I. Du Pont De Nemours And Company Transgenic fructan accumulating crops and methods for their production
WO1996027674A1 (en) 1995-03-08 1996-09-12 Hoechst Schering Agrevo Gmbh Modified starch from plants, plants synthesizing this starch, and process for its preparation
US5561236A (en) 1986-03-11 1996-10-01 Plant Genetic Systems Genetically engineered plant cells and plants exhibiting resistance to glutamine synthetase inhibitors, DNA fragments and recombinants for use in the production of said cells and plants
WO1996033270A1 (en) 1995-04-20 1996-10-24 American Cyanamid Company Structure-based designed herbicide resistant products
WO1996034968A2 (en) 1995-05-05 1996-11-07 National Starch And Chemical Investment Holding Corporation Improvements in or relating to plant starch composition
WO1996038567A2 (en) 1995-06-02 1996-12-05 Rhone-Poulenc Agrochimie Dna sequence of a gene of hydroxy-phenyl pyruvate dioxygenase and production of plants containing a gene of hydroxy-phenyl pyruvate dioxygenase and which are tolerant to certain herbicides
US5605011A (en) 1986-08-26 1997-02-25 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
WO1997011188A1 (en) 1995-09-19 1997-03-27 Planttec Biotechnologie Gmbh Plants which synthesise a modified starch, process for the production thereof and modified starch
US5637489A (en) 1986-08-23 1997-06-10 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
WO1997020936A1 (en) 1995-12-06 1997-06-12 Zeneca Limited Modification of starch synthesis in plants
WO1997026362A1 (en) 1996-01-16 1997-07-24 Planttec Biotechnologie Gmbh Nucleic acid molecules from plants coding enzymes which participate in the starch synthesis
WO1997032985A1 (en) 1996-03-07 1997-09-12 Planttec Biotechnologie Gmbh Forschung & Entwicklung Nucleic acid molecules coding for debranching enzymes from maize
WO1997041218A1 (en) 1996-04-29 1997-11-06 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Herbicide resistant rice
WO1997042328A1 (en) 1996-05-06 1997-11-13 Planttec Biotechnologie Gmbh Nucleic acid molecules which code the potato debranching enzyme
WO1997044472A1 (en) 1996-05-17 1997-11-27 Planttec Biotechnologie Gmbh Nucleic acid molecules coding soluble maize starch synthases
WO1997045545A1 (en) 1996-05-29 1997-12-04 Hoechst Schering Agrevo Gmbh Nucleic acid molecules encoding enzymes from wheat which are involved in starch synthesis
WO1997047808A1 (en) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
WO1997047806A1 (en) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
WO1997047807A1 (en) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
WO1998000549A1 (en) 1996-06-27 1998-01-08 The Australian National University MANIPULATION OF CELLULOSE AND/OR β-1,4-GLUCAN
US5712107A (en) 1995-06-07 1998-01-27 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
US5731180A (en) 1991-07-31 1998-03-24 American Cyanamid Company Imidazolinone resistant AHAS mutants
US5739082A (en) 1990-02-02 1998-04-14 Hoechst Schering Agrevo Gmbh Method of improving the yield of herbicide-resistant crop plants
EP0837944A2 (en) 1995-07-19 1998-04-29 Rhone-Poulenc Agrochimie Mutated 5-enol pyruvylshikimate-3-phosphate synthase, gene coding for said protein and transformed plants containing said gene
WO1998020145A2 (en) 1996-11-05 1998-05-14 National Starch And Chemical Investment Holding Corporation Improvements in or relating to starch content of plants
WO1998022604A1 (en) 1996-11-20 1998-05-28 Pioneer Hi-Bred International, Inc. Methods of producing high-oil seed by modification of starch levels
WO1998027212A1 (en) 1996-12-19 1998-06-25 Planttec Biotechnologie Gmbh Novel nucleic acid molecules from maize and their use for the production of modified starch
US5773702A (en) 1996-07-17 1998-06-30 Board Of Trustees Operating Michigan State University Imidazolinone herbicide resistant sugar beet plants
WO1998027806A1 (en) 1996-12-24 1998-07-02 Pioneer Hi-Bred International, Inc. Oilseed brassica containing an improved fertility restorer gene for ogura cytoplasmic male sterility
WO1998032326A2 (en) 1997-01-24 1998-07-30 Pioneer Hi-Bred International, Inc. Methods for $i(agrobacterium)-mediated transformation
WO1998039460A1 (en) 1997-03-04 1998-09-11 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Nucleic acid molecules from artichoke ($i(cynara scolymus)) encoding enzymes having fructosyl polymerase activity
WO1998040503A1 (en) 1997-03-10 1998-09-17 Planttec Biotechnologie Gmbh Nucleic acid molecules encoding starch phosphorylase from maize
US5824790A (en) 1994-06-21 1998-10-20 Zeneca Limited Modification of starch synthesis in plants
US5840946A (en) 1987-12-31 1998-11-24 Pioneer Hi-Bred International, Inc. Vegetable oil extracted from rapeseeds having a genetically controlled unusually high oleic acid content
WO1999012950A2 (en) 1997-09-06 1999-03-18 National Starch And Chemical Investment Holding Corporation Improvements in or relating to stability of plant starches
WO1999024586A1 (en) 1997-11-07 1999-05-20 Aventis Cropscience S.A. Chimeric hydroxy-phenyl pyruvate dioxygenase, dna sequence and method for obtaining plants containing such a gene, with herbicide tolerance
WO1999024593A1 (en) 1997-11-06 1999-05-20 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Nucleic acid molecules which encode proteins having fructosyl transferase activity and methods for producing long-chain inulin
US5908810A (en) 1990-02-02 1999-06-01 Hoechst Schering Agrevo Gmbh Method of improving the growth of crop plants which are resistant to glutamine synthetase inhibitors
WO1999034008A1 (en) 1997-12-24 1999-07-08 Aventis Cropscience S.A. Method for enzymatic preparation of homogentisate
US5928937A (en) 1995-04-20 1999-07-27 American Cyanamid Company Structure-based designed herbicide resistant products
US5965755A (en) 1993-10-12 1999-10-12 Agrigenetics, Inc. Oil produced from the Brassica napus
US5969169A (en) 1993-04-27 1999-10-19 Cargill, Incorporated Non-hydrogenated canola oil for food applications
WO1999053072A1 (en) 1998-04-09 1999-10-21 E.I. Du Pont De Nemours And Company Starch r1 phosphorylation protein homologs
WO1999055668A1 (en) 1998-04-27 1999-11-04 Kumiai Chemical Industry Co., Ltd. 3-arylphenyl sulfide derivatives and insecticides and miticides
WO1999058690A2 (en) 1998-05-08 1999-11-18 Aventis Cropscience Gmbh Nucleic acid molecules which code for enzymes derived from wheat and which are involved in the synthesis of starch
WO1999058688A2 (en) 1998-05-08 1999-11-18 Aventis Cropscience Gmbh Nucleic acid molecules which code for enzymes derived from wheat and which are involved in the synthesis of starch
WO1999058654A2 (en) 1998-05-13 1999-11-18 Planttec Biotechnologie Gmbh Forschung & Entwicklung Transgenic plants with a modified activity of a plastidial adp/atp translocator
WO1999057965A1 (en) 1998-05-14 1999-11-18 Aventis Cropscience Gmbh Sulfonylurea-tolerant sugar beet mutants
WO1999066050A1 (en) 1998-06-15 1999-12-23 National Starch And Chemical Investment Holding Corporation Improvements in or relating to plants and plant products
US6013861A (en) 1989-05-26 2000-01-11 Zeneca Limited Plants and processes for obtaining them
WO2000004173A1 (en) 1998-07-17 2000-01-27 Aventis Cropscience N.V. Methods and means to modulate programmed cell death in eukaryotic cells
WO2000008185A1 (en) 1998-07-31 2000-02-17 Aventis Cropscience Gmbh Nucleic acid molecule coding for beta-amylase, plants synthesizing a modified starch, method of production and applications
WO2000008175A2 (en) 1998-07-31 2000-02-17 Aventis Cropscience Gmbh Nucleic acid module coding for alpha glucosidase, plants that synthesize modified starch, methods for the production and use of said plants, and modified starch
WO2000008184A1 (en) 1998-07-31 2000-02-17 Aventis Cropscience Gmbh Plants which synthesize a modified starch, methods for producing the plants, their use, and the modified starch
WO2000011192A2 (en) 1998-08-25 2000-03-02 Pioneer Hi-Bred International, Inc. Plant glutamine: fructose-6-phosphate amidotransferase nucleic acids
WO2000014249A1 (en) 1998-09-02 2000-03-16 Planttec Biotechnologie Gmbh Nucleic acid molecules encoding an amylosucrase
WO2000022140A1 (en) 1998-10-09 2000-04-20 Planttec Biotechnologie Gmbh Forschung & Entwicklung NUCLEIC ACID MOLECULES WHICH CODE A BRANCHING ENZYME FROM BACTERIA OF THE GENUS NEISSERIA, AND A METHOD FOR PRODUCING α-1,6-BRANCHED α-1,4-GLUCANS
US6063947A (en) 1996-07-03 2000-05-16 Cargill, Incorporated Canola oil having increased oleic acid and decreased linolenic acid content
WO2000028052A2 (en) 1998-11-09 2000-05-18 Planttec Biotechnologie Gmbh Nucleic acid molecules from rice encoding an r1 protein and their use for the production of modified starch
WO2000047727A2 (en) 1999-02-08 2000-08-17 Planttec Biotechnologie Gmbh Forschung & Entwicklung Nucleic acid molecules encoding alternansucrase
WO2000066747A1 (en) 1999-04-29 2000-11-09 Syngenta Limited Herbicide resistant plants
WO2000066746A1 (en) 1999-04-29 2000-11-09 Syngenta Limited Herbicide resistant plants
WO2000073422A1 (en) 1999-05-27 2000-12-07 Planttec Biotechnologie Gmbh Genetically modified plant cells and plants with an increased activity of an amylosucrase protein and a branching enzyme
WO2000077229A2 (en) 1999-06-11 2000-12-21 Aventis Cropscience Gmbh R1 protein from wheat and the use thereof for the production of modified strach
WO2001012782A2 (en) 1999-08-12 2001-02-22 Aventis Cropscience Gmbh Transgenically modified plant cells and plants having modified gbssi- and be-protein activity
WO2001012826A2 (en) 1999-08-11 2001-02-22 Aventis Cropscience Gmbh Nucleic acid molecules derived from plants which code for enzymes which are involved in the synthesis of starch
WO2001014569A2 (en) 1999-08-20 2001-03-01 Basf Plant Science Gmbh Increasing the polysaccharide content in plants
WO2001017333A1 (en) 1999-09-10 2001-03-15 Texas Tech University Transgenic fiber producing plants with increased expression of sucrose phosphate synthase
WO2001019975A2 (en) 1999-09-15 2001-03-22 National Starch And Chemical Investment Holding Corporation Plants having reduced activity in two or more starch-modifying enzymes
WO2001024615A1 (en) 1999-10-07 2001-04-12 Valigen (Us), Inc. Non-transgenic herbicide resistant plants
US6229072B1 (en) 1995-07-07 2001-05-08 Adventa Technology Ltd Cytoplasmic male sterility system production canola hybrids
US6270828B1 (en) 1993-11-12 2001-08-07 Cargrill Incorporated Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability
US6284479B1 (en) 1995-06-07 2001-09-04 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
WO2001065922A2 (en) 2000-03-09 2001-09-13 E. I. Du Pont De Nemours And Company Sulfonylurea-tolerant sunflower plants
WO2001066704A2 (en) 2000-03-09 2001-09-13 Monsanto Technology Llc Methods for making plants tolerant to glyphosate and compositions thereof
US6323392B1 (en) 1999-03-01 2001-11-27 Pioneer Hi-Bred International, Inc. Formation of brassica napus F1 hybrid seeds which exhibit a highly elevated oleic acid content and a reduced linolenic acid content in the endogenously formed oil of the seeds
WO2001098509A2 (en) 2000-06-21 2001-12-27 Syngenta Participations Ag Grain processing method and transgenic plants useful therein
WO2002012172A1 (en) 2000-08-08 2002-02-14 Dow Agrosciences Llc Unsaturated oxime ethers and their use as fungicides
WO2002026995A1 (en) 2000-09-29 2002-04-04 Syngenta Limited Herbicide resistant plants
WO2002034923A2 (en) 2000-10-23 2002-05-02 Bayer Cropscience Gmbh Monocotyledon plant cells and plants which synthesise modified starch
WO2002036782A2 (en) 2000-10-30 2002-05-10 Maxygen, Inc. Novel glyphosate n-acetyltransferase (gat) genes
WO2002036787A2 (en) 2000-10-30 2002-05-10 Bayer Cropscience S.A. Herbicide-tolerant plants through bypassing metabolic pathway
WO2002045485A1 (en) 2000-12-08 2002-06-13 Commonwealth Scienctific And Industrial Research Organisation Modification of sucrose synthase gene expression in plant tissue and uses therefor
WO2002079410A2 (en) 2001-03-30 2002-10-10 Basf Plant Science Gmbh Glucan chain length domains
WO2002101059A2 (en) 2001-06-12 2002-12-19 Bayer Cropscience Gmbh Transgenic plants synthesising high amylose starch
WO2003013226A2 (en) 2001-08-09 2003-02-20 Cibus Genetics Non-transgenic herbicide resistant plants
WO2003033540A2 (en) 2001-10-17 2003-04-24 Basf Plant Science Gmbh Starch
WO2003071860A2 (en) 2002-02-26 2003-09-04 Bayer Cropscience Gmbh Method for generating maize plants with an increased leaf starch content, and their use for making maize silage
WO2003092360A2 (en) 2002-04-30 2003-11-13 Verdia, Inc. Novel glyphosate-n-acetyltransferase (gat) genes
WO2004024928A2 (en) 2002-09-11 2004-03-25 Bayer Cropscience S.A. Transformed plants with enhanced prenylquinone biosynthesis
JP2004131392A (en) * 2002-10-08 2004-04-30 Sumitomo Chem Co Ltd Tetrazole compound and application thereof
JP2004131416A (en) * 2002-10-10 2004-04-30 Sumitomo Chem Co Ltd Tetrazole compound and plant disease controlling application thereof
US6734341B2 (en) 1999-09-02 2004-05-11 Pioneer Hi-Bred International, Inc. Starch synthase polynucleotides and their use in the production of new starches
WO2004040012A2 (en) 2002-10-29 2004-05-13 Basf Plant Science Gmbh Compositions and methods for identifying plants having increased tolerance to imidazolinone herbicides
EP1426371A1 (en) * 2001-08-20 2004-06-09 Dainippon Ink And Chemicals, Inc. Tetrazoyl oxime derivative and agricultural chemical containing the same as active ingredient
WO2004053219A2 (en) 2002-12-05 2004-06-24 Jentex Corporation Abrasive webs and methods of making the same
WO2004056999A1 (en) 2002-12-19 2004-07-08 Bayer Cropscience Gmbh Plant cells and plants which synthesize a starch with an increased final viscosity
WO2004058723A1 (en) 2002-12-24 2004-07-15 Syngenta Participations Ag Biphenyl derivatives and their use as fungicides
WO2004078983A2 (en) 2003-03-07 2004-09-16 Basf Plant Science Gmbh Enhanced amylose production in plants
WO2004090140A2 (en) 2003-04-09 2004-10-21 Bayer Bioscience N.V. Methods and means for increasing the tolerance of plants to stress conditions
WO2004106529A2 (en) 2003-05-28 2004-12-09 Basf Aktiengesellschaft Wheat plants having increased tolerance to imidazolinone herbicides
WO2005002359A2 (en) 2003-05-22 2005-01-13 Syngenta Participations Ag Modified starch, uses, methods for production thereof
WO2005002324A2 (en) 2003-07-04 2005-01-13 Institut National De La Recherche Agronomique Method of producing double low restorer lines of brassica napus having a good agronomic value
WO2005012529A1 (en) 2003-07-31 2005-02-10 Toyo Boseki Kabushiki Kaisha Plant producing hyaluronic acid
WO2005012515A2 (en) 2003-04-29 2005-02-10 Pioneer Hi-Bred International, Inc. Novel glyphosate-n-acetyltransferase (gat) genes
WO2005017157A1 (en) 2003-08-15 2005-02-24 Commonwealth Scientific And Industrial Research Organisation (Csiro) Methods and means for altering fiber characteristics in fiber-producing plants
WO2005020673A1 (en) 2003-08-29 2005-03-10 Instituto Nacional De Technologia Agropecuaria Rice plants having increased tolerance to imidazolinone herbicides
WO2005030941A1 (en) 2003-09-30 2005-04-07 Bayer Cropscience Gmbh Plants with increased activity of a class 3 branching enzyme
WO2005030942A1 (en) 2003-09-30 2005-04-07 Bayer Cropscience Gmbh Plants with reduced activity of a class 3 branching enzyme
EP1559320A1 (en) 2002-10-31 2005-08-03 Ishihara Sangyo Kaisha, Ltd. 3-benzoyl-2,4,5-substituted pyridine derivatives or salts thereof and bactericides containing the same
WO2005093093A2 (en) 2004-03-22 2005-10-06 Basf Aktiengesellschaft Methods and compositions for analyzing ahasl genes
WO2005095617A2 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Plants with increased activity of a starch phosphorylating enzyme
WO2005095619A1 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Plants with increased activity of multiple starch phosphorylating enzymes
WO2005095618A2 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Plants with reduced activity of the starch phosphorylating enzyme phosphoglucan, water dikinase
WO2005095632A2 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Methods for identifying proteins with starch phosphorylating enzymatic activity
WO2005123927A1 (en) 2004-06-21 2005-12-29 Bayer Cropscience Gmbh Plants that produce amylopectin starch with novel properties
WO2006007373A2 (en) 2004-06-16 2006-01-19 Basf Plant Science Gmbh Polynucleotides encoding mature ahasl proteins for creating imidazolinone-tolerant plants
WO2006015376A2 (en) 2004-08-04 2006-02-09 Basf Plant Science Gmbh Monocot ahass sequences and methods of use
WO2006018319A1 (en) 2004-08-18 2006-02-23 Bayer Cropscience Gmbh Plants with increased plastidic activity of r3 starch-phosphorylating enzyme
WO2006021972A1 (en) 2004-08-26 2006-03-02 Dhara Vegetable Oil And Foods Company Limited A novel cytoplasmic male sterility system for brassica species and its use for hybrid seed production in indian oilseed mustard brassica juncea
WO2006024351A1 (en) 2004-07-30 2006-03-09 Basf Agrochemical Products B.V. Herbicide-resistant sunflower plants, plynucleotides encoding herbicide-resistant acetohydroxy acid synthase large subunit proteins, and methods of use
WO2006032469A2 (en) 2004-09-24 2006-03-30 Bayer Bioscience N.V. Stress resistant plants
WO2006032538A1 (en) 2004-09-23 2006-03-30 Bayer Cropscience Gmbh Methods and means for producing hyaluronan
WO2006045633A1 (en) 2004-10-29 2006-05-04 Bayer Bioscience N.V. Stress tolerant cotton plants
WO2006060634A2 (en) 2004-12-01 2006-06-08 Basf Agrochemical Products, B.V. Novel mutation involved in increased tolerance to imidazolinone herbicides in plants
WO2006063862A1 (en) 2004-12-17 2006-06-22 Bayer Cropscience Ag Transformed plant expressing a dextransucrase and synthesizing a modified starch
WO2006072603A2 (en) 2005-01-10 2006-07-13 Bayer Cropscience Ag Transformed plant expressing a mutansucrase and synthesizing a modified starch
WO2006089633A2 (en) 2005-02-22 2006-08-31 Bayer Cropscience Ag Spiroketal-substituted cyclic ketoenols
WO2006103107A1 (en) 2005-04-01 2006-10-05 Bayer Cropscience Ag Phosphorylated waxy potato starch
WO2006108702A1 (en) 2005-04-08 2006-10-19 Bayer Cropscience Ag High-phosphate starch
JP2006304779A (en) 2005-03-30 2006-11-09 Toyobo Co Ltd Plant producing hexosamine in high productivity
WO2006133827A2 (en) 2005-06-15 2006-12-21 Bayer Bioscience N.V. Methods for increasing the resistance of plants to hypoxic conditions
WO2006136351A2 (en) 2005-06-24 2006-12-28 Bayer Bioscience N.V. Methods for altering the reactivity of plant cell walls
WO2007009823A1 (en) 2005-07-22 2007-01-25 Bayer Cropscience Ag Overexpression of starch synthase in plants
WO2007024782A2 (en) 2005-08-24 2007-03-01 Pioneer Hi-Bred International, Inc. Compositions providing tolerance to multiple herbicides and methods of use thereof
WO2007027777A2 (en) 2005-08-31 2007-03-08 Monsanto Technology Llc Nucleotide sequences encoding insecticidal proteins
WO2007039314A2 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Plants with increased hyaluronan production
WO2007039316A1 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Improved methods and means for producings hyaluronan
WO2007039315A1 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Plants with an increased production of hyaluronan ii
WO2007095229A2 (en) 2006-02-10 2007-08-23 Dow Agrosciences Llc Insecticidal n-substituted (6-haloalkylpyridin-3-yl)alkyl sulfoximines
WO2007115646A1 (en) 2006-03-31 2007-10-18 Bayer Cropscience Ag Substituted enaminocarbonyl compounds used as insecticides
WO2007115644A1 (en) 2006-03-31 2007-10-18 Bayer Cropscience Ag Substituted enaminocarbonyl compounds
WO2007115643A1 (en) 2006-03-31 2007-10-18 Bayer Cropscience Ag Substituted enaminocarbonyl compounds
WO2007149134A1 (en) 2006-06-23 2007-12-27 Dow Agrosciences Llc A method to control insects resistant to common insecticides
WO2008067911A1 (en) 2006-12-04 2008-06-12 Bayer Cropscience Ag Biphenyl-substituted spirocyclic ketoenols
WO2008140099A1 (en) * 2007-05-14 2008-11-20 Nippon Soda Co., Ltd. Tetrazoyloxime derivative and plant disease control agent
WO2009020191A1 (en) 2007-08-08 2009-02-12 Nippon Soda Co., Ltd. Tetrazoyloxime derivative and plant disease control agent
WO2010000841A1 (en) * 2008-07-04 2010-01-07 Bayer Cropscience Sa Fungicide hydroximoyl-tetrazole derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009007233A2 (en) * 2007-07-11 2009-01-15 Basf Se Pesticidal mixtures comprising sulfonamides and one or more fungicides

Patent Citations (194)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5304732A (en) 1984-03-06 1994-04-19 Mgi Pharma, Inc. Herbicide resistance in plants
US4761373A (en) 1984-03-06 1988-08-02 Molecular Genetics, Inc. Herbicide resistance in plants
US5331107A (en) 1984-03-06 1994-07-19 Mgi Pharma, Inc. Herbicide resistance in plants
US5561236A (en) 1986-03-11 1996-10-01 Plant Genetic Systems Genetically engineered plant cells and plants exhibiting resistance to glutamine synthetase inhibitors, DNA fragments and recombinants for use in the production of said cells and plants
US7112665B1 (en) 1986-03-11 2006-09-26 Bayer Bioscience N.V. Genetically engineered plant cells and plants exhibiting resistance to glutamine synthetase inhibitors, DNA fragments and recombinants for use in the production of said cells and plants
US5646024A (en) 1986-03-11 1997-07-08 Plant Genetic Systems, N.V. Genetically engineered plant cells and plants exhibiting resistance to glutamine synthetase inhibitors, DNA fragments and recombinants for use in the production of said cells and plants
US5648477A (en) 1986-03-11 1997-07-15 Plant Genetic Systems, N.V. Genetically engineered plant cells and plants exhibiting resistance to glutamine synthetase inhibitors, DNA fragments and recombinants for use in the production of said cells and plants
US5637489A (en) 1986-08-23 1997-06-10 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5273894A (en) 1986-08-23 1993-12-28 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5276268A (en) 1986-08-23 1994-01-04 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5605011A (en) 1986-08-26 1997-02-25 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5378824A (en) 1986-08-26 1995-01-03 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5141870A (en) 1987-07-27 1992-08-25 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5840946A (en) 1987-12-31 1998-11-24 Pioneer Hi-Bred International, Inc. Vegetable oil extracted from rapeseeds having a genetically controlled unusually high oleic acid content
WO1989010396A1 (en) 1988-04-28 1989-11-02 Plant Genetic Systems N.V. Plants with modified stamen cells
US5084082A (en) 1988-09-22 1992-01-28 E. I. Du Pont De Nemours And Company Soybean plants with dominant selectable trait for herbicide resistance
US6013861A (en) 1989-05-26 2000-01-11 Zeneca Limited Plants and processes for obtaining them
WO1991002069A1 (en) 1989-08-10 1991-02-21 Plant Genetic Systems N.V. Plants with modified flowers
US5739082A (en) 1990-02-02 1998-04-14 Hoechst Schering Agrevo Gmbh Method of improving the yield of herbicide-resistant crop plants
US5908810A (en) 1990-02-02 1999-06-01 Hoechst Schering Agrevo Gmbh Method of improving the growth of crop plants which are resistant to glutamine synthetase inhibitors
US5434283A (en) 1990-04-04 1995-07-18 Pioneer Hi-Bred International, Inc. Edible endogenous vegetable oil extracted from rapeseeds of reduced stearic and palmitic saturated fatty acid content
US5198599A (en) 1990-06-05 1993-03-30 Idaho Resarch Foundation, Inc. Sulfonylurea herbicide resistance in plants
US5463175A (en) 1990-06-25 1995-10-31 Monsanto Company Glyphosate tolerant plants
US5776760A (en) 1990-06-25 1998-07-07 Monsanto Company Glyphosate tolerant plants
EP0539588A1 (en) 1990-07-05 1993-05-05 Nippon Soda Co., Ltd. Amine derivative
WO1992005251A1 (en) 1990-09-21 1992-04-02 Institut National De La Recherche Agronomique Dna sequence imparting cytoplasmic male sterility, mitochondrial genome, nuclear genome, mitochondria and plant containing said sequence and process for the preparation of hybrids
EP0571427A1 (en) 1991-02-13 1993-12-01 Hoechst Schering AgrEvo GmbH Plasmids containing dna-sequences that cause changes in the carbohydrate concentration and the carbohydrate composition in plants, as well as plant cells and plants containing these plasmids
US5731180A (en) 1991-07-31 1998-03-24 American Cyanamid Company Imidazolinone resistant AHAS mutants
US5767361A (en) 1991-07-31 1998-06-16 American Cyanamid Company Imidazolinone resistant AHAS mutants
EP0663956A1 (en) 1992-08-12 1995-07-26 Hoechst Schering AgrEvo GmbH Dna sequences which lead to the formation of polyfructans (levans), plasmids containing these sequences as well as a process for preparing transgenic plants
WO1994004693A2 (en) 1992-08-26 1994-03-03 Zeneca Limited Novel plants and processes for obtaining them
WO1994009144A1 (en) 1992-10-14 1994-04-28 Zeneca Limited Novel plants and processes for obtaining them
WO1994011520A2 (en) 1992-11-09 1994-05-26 Zeneca Limited Novel plants and processes for obtaining them
EP0607730A1 (en) 1992-12-24 1994-07-27 International Business Machines Corporation Method of direct transferring of electrically conductive elements into a substrate
EP0609013A2 (en) 1993-01-21 1994-08-03 Matsushita Electric Industrial Co., Ltd. Recording and reproducing apparatus
EP0609022A2 (en) 1993-01-25 1994-08-03 Matsushita Electric Industrial Co., Ltd. Image encoding apparatus
WO1994021795A1 (en) 1993-03-25 1994-09-29 Ciba-Geigy Ag Novel pesticidal proteins and strains
US5969169A (en) 1993-04-27 1999-10-19 Cargill, Incorporated Non-hydrogenated canola oil for food applications
EP0709000A1 (en) 1993-07-15 1996-05-01 Siemens Ag Method and device for firing an m-pulse d.c./a.c. converter assembly consisting of a master d.c./a.c. converter and at least one slave d.c./a.c. converter
WO1995004826A1 (en) 1993-08-09 1995-02-16 Institut Für Genbiologische Forschung Berlin Gmbh Debranching enzymes and dna sequences coding them, suitable for changing the degree of branching of amylopectin starch in plants
EP0719338A1 (en) 1993-09-09 1996-07-03 Hoechst Schering AgrEvo GmbH Combination of dna sequences which enable the formation of modified starch in plant cells and plants, processes for the production of these plants and the modified starch obtainable therefrom
WO1995009910A1 (en) 1993-10-01 1995-04-13 Mitsubishi Corporation Gene that identifies sterile plant cytoplasm and process for preparing hybrid plant by using the same
US5965755A (en) 1993-10-12 1999-10-12 Agrigenetics, Inc. Oil produced from the Brassica napus
US6169190B1 (en) 1993-10-12 2001-01-02 Agrigenetics Inc Oil of Brassica napus
EP0728213A1 (en) 1993-11-09 1996-08-28 E.I. Du Pont De Nemours And Company Transgenic fructan accumulating crops and methods for their production
US5908975A (en) 1993-11-09 1999-06-01 E. I. Du Pont De Nemours And Company Accumulation of fructans in plants by targeted expression of bacterial levansucrase
US6270828B1 (en) 1993-11-12 2001-08-07 Cargrill Incorporated Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability
WO1995026407A1 (en) 1994-03-25 1995-10-05 National Starch And Chemical Investment Holding Corporation Method for producing altered starch from potato plants
WO1995031553A1 (en) 1994-05-18 1995-11-23 Institut Für Genbiologische Forschung Berlin Gmbh DNA SEQUENCES CODING FOR ENZYMES CAPABLE OF FACILITATING THE SYNTHESIS OF LINEAR α-1,4 GLUCANS IN PLANTS, FUNGI AND MICROORGANISMS
WO1995035026A1 (en) 1994-06-21 1995-12-28 Zeneca Limited Novel plants and processes for obtaining them
US5824790A (en) 1994-06-21 1998-10-20 Zeneca Limited Modification of starch synthesis in plants
WO1996001904A1 (en) 1994-07-08 1996-01-25 Stichting Scheikundig Onderzoek In Nederland Production of oligosaccharides in transgenic plants
WO1996015248A1 (en) 1994-11-10 1996-05-23 Hoechst Schering Agrevo Gmbh Dna molecules that code for enzymes involved in starch synthesis, vectors, bacteria, transgenic plant cells and plants containing said molecules
WO1996019581A1 (en) 1994-12-22 1996-06-27 Hoechst Schering Agrevo Gmbh Dna molecules coding for debranching enzymes derived from plants
WO1996021023A1 (en) 1995-01-06 1996-07-11 Centrum Voor Plantenveredelings- En Reproduktieonderzoek (Cpro - Dlo) Dna sequences encoding carbohydrate polymer synthesizing enzymes and method for producing transgenic plants
WO1996027674A1 (en) 1995-03-08 1996-09-12 Hoechst Schering Agrevo Gmbh Modified starch from plants, plants synthesizing this starch, and process for its preparation
US5928937A (en) 1995-04-20 1999-07-27 American Cyanamid Company Structure-based designed herbicide resistant products
WO1996033270A1 (en) 1995-04-20 1996-10-24 American Cyanamid Company Structure-based designed herbicide resistant products
WO1996034968A2 (en) 1995-05-05 1996-11-07 National Starch And Chemical Investment Holding Corporation Improvements in or relating to plant starch composition
WO1996038567A2 (en) 1995-06-02 1996-12-05 Rhone-Poulenc Agrochimie Dna sequence of a gene of hydroxy-phenyl pyruvate dioxygenase and production of plants containing a gene of hydroxy-phenyl pyruvate dioxygenase and which are tolerant to certain herbicides
US6284479B1 (en) 1995-06-07 2001-09-04 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
US5712107A (en) 1995-06-07 1998-01-27 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
US20020031826A1 (en) 1995-06-07 2002-03-14 Nichols Scott E. Glucan-containing compositions and paper
US6229072B1 (en) 1995-07-07 2001-05-08 Adventa Technology Ltd Cytoplasmic male sterility system production canola hybrids
EP0837944A2 (en) 1995-07-19 1998-04-29 Rhone-Poulenc Agrochimie Mutated 5-enol pyruvylshikimate-3-phosphate synthase, gene coding for said protein and transformed plants containing said gene
WO1997011188A1 (en) 1995-09-19 1997-03-27 Planttec Biotechnologie Gmbh Plants which synthesise a modified starch, process for the production thereof and modified starch
WO1997020936A1 (en) 1995-12-06 1997-06-12 Zeneca Limited Modification of starch synthesis in plants
WO1997026362A1 (en) 1996-01-16 1997-07-24 Planttec Biotechnologie Gmbh Nucleic acid molecules from plants coding enzymes which participate in the starch synthesis
WO1997032985A1 (en) 1996-03-07 1997-09-12 Planttec Biotechnologie Gmbh Forschung & Entwicklung Nucleic acid molecules coding for debranching enzymes from maize
WO1997041218A1 (en) 1996-04-29 1997-11-06 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Herbicide resistant rice
WO1997042328A1 (en) 1996-05-06 1997-11-13 Planttec Biotechnologie Gmbh Nucleic acid molecules which code the potato debranching enzyme
WO1997044472A1 (en) 1996-05-17 1997-11-27 Planttec Biotechnologie Gmbh Nucleic acid molecules coding soluble maize starch synthases
WO1997045545A1 (en) 1996-05-29 1997-12-04 Hoechst Schering Agrevo Gmbh Nucleic acid molecules encoding enzymes from wheat which are involved in starch synthesis
WO1997047806A1 (en) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
WO1997047808A1 (en) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
WO1997047807A1 (en) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
WO1998000549A1 (en) 1996-06-27 1998-01-08 The Australian National University MANIPULATION OF CELLULOSE AND/OR β-1,4-GLUCAN
US6063947A (en) 1996-07-03 2000-05-16 Cargill, Incorporated Canola oil having increased oleic acid and decreased linolenic acid content
US5773702A (en) 1996-07-17 1998-06-30 Board Of Trustees Operating Michigan State University Imidazolinone herbicide resistant sugar beet plants
WO1998020145A2 (en) 1996-11-05 1998-05-14 National Starch And Chemical Investment Holding Corporation Improvements in or relating to starch content of plants
WO1998022604A1 (en) 1996-11-20 1998-05-28 Pioneer Hi-Bred International, Inc. Methods of producing high-oil seed by modification of starch levels
WO1998027212A1 (en) 1996-12-19 1998-06-25 Planttec Biotechnologie Gmbh Novel nucleic acid molecules from maize and their use for the production of modified starch
WO1998027806A1 (en) 1996-12-24 1998-07-02 Pioneer Hi-Bred International, Inc. Oilseed brassica containing an improved fertility restorer gene for ogura cytoplasmic male sterility
WO1998032326A2 (en) 1997-01-24 1998-07-30 Pioneer Hi-Bred International, Inc. Methods for $i(agrobacterium)-mediated transformation
WO1998039460A1 (en) 1997-03-04 1998-09-11 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Nucleic acid molecules from artichoke ($i(cynara scolymus)) encoding enzymes having fructosyl polymerase activity
WO1998040503A1 (en) 1997-03-10 1998-09-17 Planttec Biotechnologie Gmbh Nucleic acid molecules encoding starch phosphorylase from maize
WO1999012950A2 (en) 1997-09-06 1999-03-18 National Starch And Chemical Investment Holding Corporation Improvements in or relating to stability of plant starches
WO1999024593A1 (en) 1997-11-06 1999-05-20 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Nucleic acid molecules which encode proteins having fructosyl transferase activity and methods for producing long-chain inulin
WO1999024585A1 (en) 1997-11-07 1999-05-20 Aventis Cropscience S.A. Mutated hydroxy-phenyl pyruvate dioxygenase, dna sequence and method for obtaining herbicide-tolerant plants containing such gene
WO1999024586A1 (en) 1997-11-07 1999-05-20 Aventis Cropscience S.A. Chimeric hydroxy-phenyl pyruvate dioxygenase, dna sequence and method for obtaining plants containing such a gene, with herbicide tolerance
WO1999034008A1 (en) 1997-12-24 1999-07-08 Aventis Cropscience S.A. Method for enzymatic preparation of homogentisate
WO1999053072A1 (en) 1998-04-09 1999-10-21 E.I. Du Pont De Nemours And Company Starch r1 phosphorylation protein homologs
WO1999055668A1 (en) 1998-04-27 1999-11-04 Kumiai Chemical Industry Co., Ltd. 3-arylphenyl sulfide derivatives and insecticides and miticides
WO1999058688A2 (en) 1998-05-08 1999-11-18 Aventis Cropscience Gmbh Nucleic acid molecules which code for enzymes derived from wheat and which are involved in the synthesis of starch
WO1999058690A2 (en) 1998-05-08 1999-11-18 Aventis Cropscience Gmbh Nucleic acid molecules which code for enzymes derived from wheat and which are involved in the synthesis of starch
WO1999058654A2 (en) 1998-05-13 1999-11-18 Planttec Biotechnologie Gmbh Forschung & Entwicklung Transgenic plants with a modified activity of a plastidial adp/atp translocator
WO1999057965A1 (en) 1998-05-14 1999-11-18 Aventis Cropscience Gmbh Sulfonylurea-tolerant sugar beet mutants
WO1999066050A1 (en) 1998-06-15 1999-12-23 National Starch And Chemical Investment Holding Corporation Improvements in or relating to plants and plant products
WO2000004173A1 (en) 1998-07-17 2000-01-27 Aventis Cropscience N.V. Methods and means to modulate programmed cell death in eukaryotic cells
WO2000008184A1 (en) 1998-07-31 2000-02-17 Aventis Cropscience Gmbh Plants which synthesize a modified starch, methods for producing the plants, their use, and the modified starch
WO2000008175A2 (en) 1998-07-31 2000-02-17 Aventis Cropscience Gmbh Nucleic acid module coding for alpha glucosidase, plants that synthesize modified starch, methods for the production and use of said plants, and modified starch
WO2000008185A1 (en) 1998-07-31 2000-02-17 Aventis Cropscience Gmbh Nucleic acid molecule coding for beta-amylase, plants synthesizing a modified starch, method of production and applications
WO2000011192A2 (en) 1998-08-25 2000-03-02 Pioneer Hi-Bred International, Inc. Plant glutamine: fructose-6-phosphate amidotransferase nucleic acids
WO2000014249A1 (en) 1998-09-02 2000-03-16 Planttec Biotechnologie Gmbh Nucleic acid molecules encoding an amylosucrase
WO2000022140A1 (en) 1998-10-09 2000-04-20 Planttec Biotechnologie Gmbh Forschung & Entwicklung NUCLEIC ACID MOLECULES WHICH CODE A BRANCHING ENZYME FROM BACTERIA OF THE GENUS NEISSERIA, AND A METHOD FOR PRODUCING α-1,6-BRANCHED α-1,4-GLUCANS
WO2000028052A2 (en) 1998-11-09 2000-05-18 Planttec Biotechnologie Gmbh Nucleic acid molecules from rice encoding an r1 protein and their use for the production of modified starch
WO2000047727A2 (en) 1999-02-08 2000-08-17 Planttec Biotechnologie Gmbh Forschung & Entwicklung Nucleic acid molecules encoding alternansucrase
US6323392B1 (en) 1999-03-01 2001-11-27 Pioneer Hi-Bred International, Inc. Formation of brassica napus F1 hybrid seeds which exhibit a highly elevated oleic acid content and a reduced linolenic acid content in the endogenously formed oil of the seeds
WO2000066746A1 (en) 1999-04-29 2000-11-09 Syngenta Limited Herbicide resistant plants
WO2000066747A1 (en) 1999-04-29 2000-11-09 Syngenta Limited Herbicide resistant plants
WO2000073422A1 (en) 1999-05-27 2000-12-07 Planttec Biotechnologie Gmbh Genetically modified plant cells and plants with an increased activity of an amylosucrase protein and a branching enzyme
WO2000077229A2 (en) 1999-06-11 2000-12-21 Aventis Cropscience Gmbh R1 protein from wheat and the use thereof for the production of modified strach
WO2001012826A2 (en) 1999-08-11 2001-02-22 Aventis Cropscience Gmbh Nucleic acid molecules derived from plants which code for enzymes which are involved in the synthesis of starch
WO2001012782A2 (en) 1999-08-12 2001-02-22 Aventis Cropscience Gmbh Transgenically modified plant cells and plants having modified gbssi- and be-protein activity
WO2001014569A2 (en) 1999-08-20 2001-03-01 Basf Plant Science Gmbh Increasing the polysaccharide content in plants
US6734341B2 (en) 1999-09-02 2004-05-11 Pioneer Hi-Bred International, Inc. Starch synthase polynucleotides and their use in the production of new starches
WO2001017333A1 (en) 1999-09-10 2001-03-15 Texas Tech University Transgenic fiber producing plants with increased expression of sucrose phosphate synthase
WO2001019975A2 (en) 1999-09-15 2001-03-22 National Starch And Chemical Investment Holding Corporation Plants having reduced activity in two or more starch-modifying enzymes
WO2001024615A1 (en) 1999-10-07 2001-04-12 Valigen (Us), Inc. Non-transgenic herbicide resistant plants
WO2001065922A2 (en) 2000-03-09 2001-09-13 E. I. Du Pont De Nemours And Company Sulfonylurea-tolerant sunflower plants
WO2001066704A2 (en) 2000-03-09 2001-09-13 Monsanto Technology Llc Methods for making plants tolerant to glyphosate and compositions thereof
WO2001098509A2 (en) 2000-06-21 2001-12-27 Syngenta Participations Ag Grain processing method and transgenic plants useful therein
WO2002012172A1 (en) 2000-08-08 2002-02-14 Dow Agrosciences Llc Unsaturated oxime ethers and their use as fungicides
WO2002026995A1 (en) 2000-09-29 2002-04-04 Syngenta Limited Herbicide resistant plants
WO2002034923A2 (en) 2000-10-23 2002-05-02 Bayer Cropscience Gmbh Monocotyledon plant cells and plants which synthesise modified starch
WO2002036782A2 (en) 2000-10-30 2002-05-10 Maxygen, Inc. Novel glyphosate n-acetyltransferase (gat) genes
WO2002036787A2 (en) 2000-10-30 2002-05-10 Bayer Cropscience S.A. Herbicide-tolerant plants through bypassing metabolic pathway
WO2002045485A1 (en) 2000-12-08 2002-06-13 Commonwealth Scienctific And Industrial Research Organisation Modification of sucrose synthase gene expression in plant tissue and uses therefor
WO2002079410A2 (en) 2001-03-30 2002-10-10 Basf Plant Science Gmbh Glucan chain length domains
WO2002101059A2 (en) 2001-06-12 2002-12-19 Bayer Cropscience Gmbh Transgenic plants synthesising high amylose starch
WO2003013226A2 (en) 2001-08-09 2003-02-20 Cibus Genetics Non-transgenic herbicide resistant plants
US20050070439A1 (en) 2001-08-20 2005-03-31 Dainippon Ink And Chemicals, Inc. Tetrazoyl oxime derivative and agricultural chemical containing the same as active ingredient
EP1426371A1 (en) * 2001-08-20 2004-06-09 Dainippon Ink And Chemicals, Inc. Tetrazoyl oxime derivative and agricultural chemical containing the same as active ingredient
WO2003033540A2 (en) 2001-10-17 2003-04-24 Basf Plant Science Gmbh Starch
WO2003071860A2 (en) 2002-02-26 2003-09-04 Bayer Cropscience Gmbh Method for generating maize plants with an increased leaf starch content, and their use for making maize silage
WO2003092360A2 (en) 2002-04-30 2003-11-13 Verdia, Inc. Novel glyphosate-n-acetyltransferase (gat) genes
WO2004024928A2 (en) 2002-09-11 2004-03-25 Bayer Cropscience S.A. Transformed plants with enhanced prenylquinone biosynthesis
JP2004131392A (en) * 2002-10-08 2004-04-30 Sumitomo Chem Co Ltd Tetrazole compound and application thereof
JP2004131416A (en) * 2002-10-10 2004-04-30 Sumitomo Chem Co Ltd Tetrazole compound and plant disease controlling application thereof
WO2004040012A2 (en) 2002-10-29 2004-05-13 Basf Plant Science Gmbh Compositions and methods for identifying plants having increased tolerance to imidazolinone herbicides
EP1559320A1 (en) 2002-10-31 2005-08-03 Ishihara Sangyo Kaisha, Ltd. 3-benzoyl-2,4,5-substituted pyridine derivatives or salts thereof and bactericides containing the same
WO2004053219A2 (en) 2002-12-05 2004-06-24 Jentex Corporation Abrasive webs and methods of making the same
WO2004056999A1 (en) 2002-12-19 2004-07-08 Bayer Cropscience Gmbh Plant cells and plants which synthesize a starch with an increased final viscosity
WO2004058723A1 (en) 2002-12-24 2004-07-15 Syngenta Participations Ag Biphenyl derivatives and their use as fungicides
WO2004078983A2 (en) 2003-03-07 2004-09-16 Basf Plant Science Gmbh Enhanced amylose production in plants
WO2004090140A2 (en) 2003-04-09 2004-10-21 Bayer Bioscience N.V. Methods and means for increasing the tolerance of plants to stress conditions
WO2005012515A2 (en) 2003-04-29 2005-02-10 Pioneer Hi-Bred International, Inc. Novel glyphosate-n-acetyltransferase (gat) genes
WO2005002359A2 (en) 2003-05-22 2005-01-13 Syngenta Participations Ag Modified starch, uses, methods for production thereof
WO2004106529A2 (en) 2003-05-28 2004-12-09 Basf Aktiengesellschaft Wheat plants having increased tolerance to imidazolinone herbicides
WO2005002324A2 (en) 2003-07-04 2005-01-13 Institut National De La Recherche Agronomique Method of producing double low restorer lines of brassica napus having a good agronomic value
WO2005012529A1 (en) 2003-07-31 2005-02-10 Toyo Boseki Kabushiki Kaisha Plant producing hyaluronic acid
WO2005017157A1 (en) 2003-08-15 2005-02-24 Commonwealth Scientific And Industrial Research Organisation (Csiro) Methods and means for altering fiber characteristics in fiber-producing plants
WO2005020673A1 (en) 2003-08-29 2005-03-10 Instituto Nacional De Technologia Agropecuaria Rice plants having increased tolerance to imidazolinone herbicides
WO2005030942A1 (en) 2003-09-30 2005-04-07 Bayer Cropscience Gmbh Plants with reduced activity of a class 3 branching enzyme
WO2005030941A1 (en) 2003-09-30 2005-04-07 Bayer Cropscience Gmbh Plants with increased activity of a class 3 branching enzyme
WO2005095617A2 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Plants with increased activity of a starch phosphorylating enzyme
WO2005095619A1 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Plants with increased activity of multiple starch phosphorylating enzymes
WO2005095618A2 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Plants with reduced activity of the starch phosphorylating enzyme phosphoglucan, water dikinase
WO2005095632A2 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Methods for identifying proteins with starch phosphorylating enzymatic activity
WO2005093093A2 (en) 2004-03-22 2005-10-06 Basf Aktiengesellschaft Methods and compositions for analyzing ahasl genes
WO2006007373A2 (en) 2004-06-16 2006-01-19 Basf Plant Science Gmbh Polynucleotides encoding mature ahasl proteins for creating imidazolinone-tolerant plants
WO2005123927A1 (en) 2004-06-21 2005-12-29 Bayer Cropscience Gmbh Plants that produce amylopectin starch with novel properties
WO2006024351A1 (en) 2004-07-30 2006-03-09 Basf Agrochemical Products B.V. Herbicide-resistant sunflower plants, plynucleotides encoding herbicide-resistant acetohydroxy acid synthase large subunit proteins, and methods of use
WO2006015376A2 (en) 2004-08-04 2006-02-09 Basf Plant Science Gmbh Monocot ahass sequences and methods of use
WO2006018319A1 (en) 2004-08-18 2006-02-23 Bayer Cropscience Gmbh Plants with increased plastidic activity of r3 starch-phosphorylating enzyme
WO2006021972A1 (en) 2004-08-26 2006-03-02 Dhara Vegetable Oil And Foods Company Limited A novel cytoplasmic male sterility system for brassica species and its use for hybrid seed production in indian oilseed mustard brassica juncea
WO2006032538A1 (en) 2004-09-23 2006-03-30 Bayer Cropscience Gmbh Methods and means for producing hyaluronan
WO2006032469A2 (en) 2004-09-24 2006-03-30 Bayer Bioscience N.V. Stress resistant plants
WO2006045633A1 (en) 2004-10-29 2006-05-04 Bayer Bioscience N.V. Stress tolerant cotton plants
WO2006060634A2 (en) 2004-12-01 2006-06-08 Basf Agrochemical Products, B.V. Novel mutation involved in increased tolerance to imidazolinone herbicides in plants
WO2006063862A1 (en) 2004-12-17 2006-06-22 Bayer Cropscience Ag Transformed plant expressing a dextransucrase and synthesizing a modified starch
WO2006072603A2 (en) 2005-01-10 2006-07-13 Bayer Cropscience Ag Transformed plant expressing a mutansucrase and synthesizing a modified starch
WO2006089633A2 (en) 2005-02-22 2006-08-31 Bayer Cropscience Ag Spiroketal-substituted cyclic ketoenols
JP2006304779A (en) 2005-03-30 2006-11-09 Toyobo Co Ltd Plant producing hexosamine in high productivity
WO2006103107A1 (en) 2005-04-01 2006-10-05 Bayer Cropscience Ag Phosphorylated waxy potato starch
WO2006108702A1 (en) 2005-04-08 2006-10-19 Bayer Cropscience Ag High-phosphate starch
WO2006133827A2 (en) 2005-06-15 2006-12-21 Bayer Bioscience N.V. Methods for increasing the resistance of plants to hypoxic conditions
WO2006136351A2 (en) 2005-06-24 2006-12-28 Bayer Bioscience N.V. Methods for altering the reactivity of plant cell walls
WO2007009823A1 (en) 2005-07-22 2007-01-25 Bayer Cropscience Ag Overexpression of starch synthase in plants
WO2007024782A2 (en) 2005-08-24 2007-03-01 Pioneer Hi-Bred International, Inc. Compositions providing tolerance to multiple herbicides and methods of use thereof
WO2007027777A2 (en) 2005-08-31 2007-03-08 Monsanto Technology Llc Nucleotide sequences encoding insecticidal proteins
WO2007039315A1 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Plants with an increased production of hyaluronan ii
WO2007039316A1 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Improved methods and means for producings hyaluronan
WO2007039314A2 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Plants with increased hyaluronan production
WO2007095229A2 (en) 2006-02-10 2007-08-23 Dow Agrosciences Llc Insecticidal n-substituted (6-haloalkylpyridin-3-yl)alkyl sulfoximines
WO2007115646A1 (en) 2006-03-31 2007-10-18 Bayer Cropscience Ag Substituted enaminocarbonyl compounds used as insecticides
WO2007115644A1 (en) 2006-03-31 2007-10-18 Bayer Cropscience Ag Substituted enaminocarbonyl compounds
WO2007115643A1 (en) 2006-03-31 2007-10-18 Bayer Cropscience Ag Substituted enaminocarbonyl compounds
WO2007149134A1 (en) 2006-06-23 2007-12-27 Dow Agrosciences Llc A method to control insects resistant to common insecticides
WO2008067911A1 (en) 2006-12-04 2008-06-12 Bayer Cropscience Ag Biphenyl-substituted spirocyclic ketoenols
WO2008140099A1 (en) * 2007-05-14 2008-11-20 Nippon Soda Co., Ltd. Tetrazoyloxime derivative and plant disease control agent
WO2009020191A1 (en) 2007-08-08 2009-02-12 Nippon Soda Co., Ltd. Tetrazoyloxime derivative and plant disease control agent
WO2010000841A1 (en) * 2008-07-04 2010-01-07 Bayer Cropscience Sa Fungicide hydroximoyl-tetrazole derivatives

Non-Patent Citations (14)

* Cited by examiner, † Cited by third party
Title
"Isoboles, a graphic representation of synergism in pesticides", JOURNAL OF PLANT PATHOLOGY, vol. 70, 1964, pages 73 - 80
"Isoboles, a graphic representation of synergism in pesticides", NETHERLANDS JOURNAL OF PLANT PATHOLOGY, vol. 70, 1964, pages 73 - 80
BARRY ET AL., CURR. TOPICS PLANT PHYSIOL., vol. 7, 1992, pages 139 - 145
COLBY, S.R.: "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", WEEDS, vol. 15, 1967, pages 20 - 22
COLBY: "Calculation of the synergistic and antagonistic responses of herbicide combinations", WEEDS, vol. 15, 1967, pages 20 - 22
COMAI ET AL., SCIENCE, vol. 221, 1983, pages 370 - 371
CRICKMORE ET AL., MICROBIOLOGY AND MOLECULAR BIOLOGY REVIEWS, vol. 62, 1998, pages 807 - 813
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 30 April 2004 (2004-04-30), ARAKI, TOMOHIRO: "Preparation of tetrazoles, plant disease-controlling agents containing them, and method for controlling plant diseases using them", XP002538151, retrieved from STN Database accession no. 2004:351603 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 30 April 2004 (2004-04-30), ARAKI, TOMOHIRO: "Preparation of tetrazoles, plant disease-controlling agents containing them, and method for controlling plant diseases with them", XP002538150, retrieved from STN Database accession no. 2004:354285 *
GASSER ET AL., J. BIOL. CHEM., vol. 263, 1988, pages 4280 - 4289
MOELLENBECK ET AL., NAT. BIOTECHNOL., vol. 19, 2001, pages 668 - 72
SCHNEPF ET AL., APPLIED ENVIRONM. MICROBIOL., vol. 71, 2006, pages 1765 - 1774
SHAH ET AL., SCIENCE, vol. 233, 1986, pages 478 - 481
TRANEL; WRIGHT, WEED SCIENCE, vol. 50, 2002, pages 700 - 712

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016188221A (en) * 2010-10-07 2016-11-04 バイエル・クロップサイエンス・アクチェンゲゼルシャフト Fungicide composition comprising a tetrazolyloxime derivative and a thiazolylpiperidine derivative
WO2012045798A1 (en) 2010-10-07 2012-04-12 Bayer Cropscience Ag Fungicide composition comprising a tetrazolyloxime derivative and a thiazolylpiperidine derivative
CN103338638A (en) * 2010-10-07 2013-10-02 拜尔农科股份公司 Fungicide composition comprising a tetrazolyloxime derivative and a thiazolylpiperidine derivative
KR20130117788A (en) * 2010-10-07 2013-10-28 바이엘 크롭사이언스 아게 Fungicide composition comprising a tetrazolyloxime derivative and a thiazolylpiperidine derivative
JP2013542934A (en) * 2010-10-07 2013-11-28 バイエル・クロップサイエンス・アーゲー Bactericidal composition comprising a tetrazolyl oxime derivative and a thiazolyl piperidine derivative
US9408391B2 (en) 2010-10-07 2016-08-09 Bayer Intellectual Property Gmbh Fungicide composition comprising a tetrazolyloxime derivative and a thiazolylpiperidine derivative
KR101871525B1 (en) * 2010-10-07 2018-06-26 바이엘 크롭사이언스 악티엔게젤샤프트 Fungicide composition comprising a tetrazolyloxime derivative and a thiazolylpiperidine derivative
WO2012088645A1 (en) * 2010-12-31 2012-07-05 Bayer Cropscience Ag Method for improving plant quality
CN102037969B (en) * 2011-01-12 2014-06-18 陕西美邦农药有限公司 Sterilization composition containing imibenconazole and methoxyl acrylate compound
CN102037969A (en) * 2011-01-12 2011-05-04 陕西美邦农药有限公司 Sterilization composition containing imibenconazole and methoxyl acrylate compound
CN103651428A (en) * 2011-05-17 2014-03-26 陕西韦尔奇作物保护有限公司 Insecticidal composition containing furan tebufenozide and antibiotic compound
EP2921491A1 (en) * 2011-12-27 2015-09-23 Bayer Intellectual Property GmbH Intermediates for the production of heteroarylpiperidine and heteroarylpiperazine derivatives as fungicides
JP2018150308A (en) * 2011-12-27 2018-09-27 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH Heteroarylpiperidine and piperazine derivatives as fungicides
CN104470364A (en) * 2012-05-01 2015-03-25 帝斯曼知识产权资产管理有限公司 Antifungal compositions
CN103583522B (en) * 2012-08-17 2015-04-15 陕西美邦农药有限公司 Bactericidal composition containing fenarimol and strobilurin
CN103583522A (en) * 2012-08-17 2014-02-19 陕西美邦农药有限公司 Bactericidal composition containing fenarimol and strobilurin
CN103641795B (en) * 2013-04-18 2016-03-02 南开大学 One class contains acetophenone derivs of 1,2,3-thiadiazoles and its production and use
CN103641795A (en) * 2013-04-18 2014-03-19 南开大学 Acetophenone derivatives containing 1,2,3-thiadiazole and preparation method and use thereof
WO2015141867A1 (en) 2014-03-20 2015-09-24 Mitsui Chemicals Agro, Inc. Plant disease control composition and method for controlling plant disease by application of same
CN104502510A (en) * 2014-12-30 2015-04-08 山东出入境检验检疫局检验检疫技术中心 GC-NCI-MS (Gas Chromatography-Negative Chemical Ionization-Mass Spectrum) detecting method for residual quantity of cyenopyrafen in fruits and vegetables
WO2021153748A1 (en) 2020-01-29 2021-08-05 日本曹達株式会社 Agricultural and horticultural composition

Also Published As

Publication number Publication date
JP2012518028A (en) 2012-08-09
AR075698A1 (en) 2011-04-20
US20120027741A1 (en) 2012-02-02
TW201031331A (en) 2010-09-01
EP2398326A1 (en) 2011-12-28

Similar Documents

Publication Publication Date Title
US20120027741A1 (en) Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance
EP2424373B1 (en) Compositions comprising a strigolactone compound and a chito-oligosaccharide compound for enhanced plant growth and yield
CA2811698C (en) Use of active ingredients for controlling nematodes in nematode-resistant crops
JP6342447B2 (en) Bactericidal composition comprising a tetrazolyl oxime derivative and a thiazolyl piperidine derivative
MX2013004278A (en) N-benzyl heterocyclic carboxamides.
US20130045995A1 (en) Fungicide hydroximoyl-heterocycles derivatives
CN103298802B (en) N-hetervaromatic methyl pyrazolyl carboxylic acid amides
WO2011015524A2 (en) Fungicide heterocycles derivatives
KR20130109959A (en) Fungicide n-[(trisubstitutedsilyl)methyl]-carboxamide derivatives
ES2719219T3 (en) Fungicidal composition comprising a tetrazolyl oxime derivative and a thiazolylpiperidine derivative
US20130116287A1 (en) Fungicide hydroximoyl-heterocycles derivatives
US20140005230A1 (en) Fungicide hydroximoyl-tetrazole derivatives
MX2013000655A (en) Benzocycloalkenes as antifungal agents.

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10706189

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2010706189

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2011550559

Country of ref document: JP

Ref document number: 13202200

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: DE