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(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2015/028034 Al 5 March 2015 (05.03.2015) P O P C T

(51) International Patent Classification: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, A01N 53/00 (2006.01) A01N 47/02 (2006.01) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, A01N 43/90 (2006.01) A01P 7/00 (2006.01) HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, A01N 57/ (2006.01) KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (21) International Application Number: OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, PCT/DK20 14/050264 SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, (22) International Filing Date: TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, 1 September 2014 (01 .09.2014) ZW. (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (26) Publication Language: English GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, (30) Priority Data: TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, PA 2013 00494 2 September 2013 (02.09.2013) DK TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (71) Applicant: CHEMINOVA A S [DK/DK]; Thyboranvej LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, 78, DK-7673 Harbo0re (DK). SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). (72) Inventor: 0STERGAARD, Niels; R0dem0llevej 20, DK- 7660 Bffikmarksbro (DK). Declarations under Rule 4.17 : (74) Agents: RASMUSSEN, Torben Ravn et al; Awapatent — as to applicant's entitlement to apply for and be granted a A/S, Rigensgade 11, DK-13 16 K0benhavn K (DK). patent (Rule 4.1 7(H)) (81) Designated States (unless otherwise indicated, for every Published: kind of national protection available): AE, AG, AL, AM, — with international search report (Art. 21(3)) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY,

o 00 (54) Title: COMBINATION OF 2,3,5, 6-TETRAFLUORO-4-METHYLBENZYL (Z)-(l R)-CIS-3-(2-CHLORO-3,3,3-TRIFLUORO-l © -PROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE WITH AT LEAST ONE , , NEMATICIDE AND/OR . o (57) Abstract: Presented are new pesticidal mixtures comprising 2,3,5, 6-tetrafluoro-4- methylbenzyl(Z)-(lR)-cis-3-(2-chloro-3,3,3- trifluoro-l-propenyl)-2,2- dimethylcyclopropanecarboxylate and one or more of compound(s) (II) which is an insecticide, acaricide, nematicide and/or fungicide. The invention relates also to methods and use of these mixtures for controlling harmful pests such as o , arachnids, and fungie.g.in and on plants, and for protecting such plants being infested with pests and also for pro - tecting seeds. COMBINATION OF 2,3,5,6-TETRAFLUORO-4-METHYLBENZYL (Z)-(1 R)-CIS-3-(2-CHLORO-3,3,3-TRIFLUORO-1 -PROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE WITH AT LEAST ONE INSECTICIDE, ACARICIDE, AND/OR FUNGICIDE

Introduction The invention relates to new pesticidal mixtures comprising a compound (I) which is 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(\R)-cis-3-(2- chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate and one or more compounds (II) chosen among , , nematicides and/or . The invention relates also to a method and use of these mixtures for controlling harmful pests (e.g. insects, arachnids, nematodes and fungi) e.g. in and on plants and non-crops, and for protecting such plants being infested with pests and also for protecting seeds.

Background One typical problem arising in the field of lies in the need to reduce the dosage rates of the active ingredient in order to reduce or avoid unfavorable environmental or toxicological effects whilst still allowing effective pest control.

Another problem encountered concerns the need to have available pest control agents which are effective against a broad spectrum of pests.

There also exists the need for pest control agents that combine knock-down activity with prolonged control, that is, fast action with long lasting action.

Another difficulty in relation to the use of is that the repeated and exclusive application of an individual pesticidal compound leads in many cases to a rapid selection of pests which have developed natural or adapted resistance against the active compound in question. Therefore there is a need for pest control agents that help prevent or overcome resistance.

It was therefore an object of the present invention to provide pesticidal mixtures which solves at least one of the discussed problems such as reducing the dosage rate, enhancing the spectrum of activity or combining knock-down activity with prolonged control or as to resistance management.

It has been found that this object is in part or in whole achieved by the combination of active compounds defined at the outset. Moreover, it has been found that simultaneous, that is joint or separate, application of an active compound (I) and one or more compounds (II) or successive application of an active compound (I) and one or more compounds (II) allows enhanced control of pests compared to the control rates that are possible with the individual compounds.

The pesticidal active compound is a racemic mixture comprised of mainly two isomers out of 8 possible due to the Z/E configuration on the vinyl group and the two chiral centers on the cyclopropane ring (IRS, RS , i.e. present in the molecule 2,3,5,6-tetrafluoro-4-methylbenzyl 3-(2-chloro-3,3,3- trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate. One of these 8 isomers being the compound (I). Tefluthrin is primarily a mixture of the two compounds (Z)-( \R)-cis-3 -(2-chloro-3,3,3-trifluoro- 1-propenyl)-2,2- dimethylcyclopropanecarboxylate and (Z)-(l,S)-czs-3-(2-chloro-3,3,3-trifluoro-l- propenyl)-2,2-dimethylcyclopropanecarboxylate; i.e. two cis-isomers. On a commercial scale, tefluthrin is produced according to methods that provide such mixture, and the single most active isomer is not easily separated. The use of tefluthrin in crop protection is well known e.g. as described in British Crop Protection Conference Pests and Diseases,(l), p . 97-106 (1986). It is known that the pesticidal effect of tefluthrin is found primarily in one of the isomers, i.e. compound (I), as described in British Crop Protection Conference Pests and Diseases, (1), p . 199-206 (1986). One would expect that when combining tefluthrin with another , the same combination would require approximately half the amount of the most active isomer (i.e. compound (I)) to provide the same pesticidal effect. However, it has now surprisingly been found that an improved effect is observed when substituting tefluthrin (including any of the other isomers) with the compound (I), preferably substantially free of any of the others isomers of 2,3,5,6-tetrafluoro-4-methylbenzyl 3-(2-chloro- 3,3,3-trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate. That is, it has been found that an improved synergistic effect is present for pesticidal mixtures comprising the compound (I) over the same mixtures comprising tefluthrin.

The unexpected finding has several important implications, e.g. both economical but also environmental in that the pesticidal mixtures as herein described preferably need only to be applied at a lower dose and advantageously without the presence of potentially detrimental isomers. It is a standard demand in crop protection to achieve an optimal effect with active ingredients at the lowest dosage rate required while simultaneously keeping the pollution of the environment as low as possible.

Description of the invention The present invention relates to a mixture comprising compound (I) which is 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(\R)-cis-3-(2-chloro-3,3,3-trifluoro- 1- propenyl)-2,2-dimethylcyclopropanecarboxylate and one or more compound(s) (II) which is either an insecticide, nematicide, acaricide or fungicide.

One aspect of the invention relates to a mixture comprising, as pesticidal active ingredients, the compound (I) and just one other compound (II) which is an insecticide, nematicide, acaricide or fungicide, i.e. a mixture containing the compound (I) and one other compound (II) which is an insecticide, nematicide, acaricide or fungicide as the sole active ingredients. Preferably the compound (II) is an insecticide, nematicides or acaricide and most preferably an insecticide or acaricide.

Another apect of the invention relates to a mixture comprising, as pesticidal active ingredients, the compound (I) and just two other compounds (II) which are selected among insecticides, nematicides, acaricides and/or fungicides, i.e. a mixture containing the compound (I) and two other compounds (II) which are selected among insecticides, nematicides, acaricides and/or fungicides as the sole active ingredients. Preferably at least one of the two compounds (II) is a insecticide or an acaricide. More preferably the second of the two compounds (II) is chosen among insecticides, nematicides or acaricides; with insecticides and acaricides being of particular use. In another aspect the two compounds (II) are both insecticides, nematicides, acaricides or fungicides, more preferably the two compounds (II) are both insecticides, nematicides or acaricides and most preferably the two compounds (II) are both insecticides or acaricides.

Compound (I) is preferably substantially free of any other isomer of 2,3,5,6- tetrafluoro-4-methylbenzyl 3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2- dimethylcyclopropanecarboxylate. Preferably the mixture of 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(\R)-cis-3-(2- chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate and one or more compounds (II) is substantially free of any other isomer of 2,3,5,6- tetrafluoro-4-methylbenzyl 3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2- dimethylcyclopropanecarboxylate. More preferably the mixture of 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(\R)-cis- 3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate and one or more compounds (II) is substantially free of 2,3,5,6-tetrafluoro-4- methylbenzyl (Z)-(l ,S - .,-3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2- dimethylcyclopropanecarb oxy1ate. With respect to the term "substantially free of any other isomer" as used herein, it shall be understood that the composition contains a greater proportion or percentage of 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(l R)- zs-3-(2-chloro-3,3,3- trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate, on a weight basis, 5 in relation to any other isomer of 2,3,5,6-tetrafluoro-4-methylbenzyl 3-(2- chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate, these percentages being based on the total amount of 2,3,5,6-tetrafluoro-4- methylbenzyl 3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2- dimethylcyclopropanecarboxylate present. 10 In a preferred embodiment, the term "substantially free of any other isomer" as used herein means that the composition contains at least 70% by weight of 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-( \R)-cis-3 -(2-chloro-3 ,3,3-trifluoro- 1- propenyl)-2,2-dimethylcyclopropanecarboxylate, and 30% by weight or less of any of the other isomers of 2,3,5,6-tetrafluoro-4-methylbenzyl 3-(2-chloro- 15 3,3,3-trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate. In a more preferred embodiment, the term "substantially free of any other isomer" means that the composition contains at least 80% by weight of 2,3,5,6- tetrafluoro-4-methylbenzyl (Z)-( \R)-cis-3 -(2-chloro-3 ,3,3-trifluoro- 1-propenyl)- 2,2-dimethylcyclopropanecarboxylate, and 20% by weight or less of 2,3,5,6- 20 tetrafluoro-4-methylbenzyl (Z)-( 1S)-cis-3-(2-chloro-3 ,3,3-trifluoro- 1-propenyl)- 2,2-dimethylcyclopropanecarboxylate or any other isomer. In a still more preferred embodiment, the term "substantially free of any other isomer" means that the composition contains at least 90% by weight of 2,3,5,6- tetrafluoro-4-methylbenzyl (Z)-( \R)-cis-3 -(2-chloro-3 ,3,3-trifluoro- 1-propenyl)- 2 5 2,2-dimethylcyclopropanecarboxylate, and 10% by weight or less of 2,3,5,6-

tetrafluoro-4-methylbenzyl (Z)-( 1S)-cis-3-(2-chloro-3 ,3,3-trifluoro- 1-propenyl)- 2,2-dimethylcyclopropanecarboxylate or any other isomer. In an even more preferred embodiment, the term "substantially free of any other isomer" means that the composition contains at least 91%, preferably at least

30 92% , more preferably 93%> by weight of 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)- (\R)-cis-3 -(2-chloro-3 ,3,3-trifluoro- 1-propenyl)-2,2- dimethylcyclopropanecarboxylate in relation to 2,3,5,6-tetrafluoro-4- methylbenzyl 3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2- dimethylcyclopropanecarboxylate or any other isomer, even more preferably at least 94%, and most preferably at least 95%. In a most preferred embodiment, the term "substantially free of any other isomer" means that the composition contains at least 96%, preferably at least 97%, more preferably at least 98%> by weight of 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(l R)- zs-3-(2-chloro-3,3,3- trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate in relation to

2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-( 1S)-cis-3-(2-chloro-3,3,3-trifluoro- 1- propenyl)-2,2-dimethylcyclopropanecarboxylate or any other isomer, even more preferably at least 99%, and most preferably at least 99.5%.

To produce the compound (I) (2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(l R)-czs- 3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate) on an industrial scale it is desirable to find methods of making the final product that avoid the use of expensive reagents and have as few chemical stages as possible. A process for the preparation of compound (I) is provided comprising a) chlorinating (Z)-(\R)-cis-3 -(2-chloro-3,3,3-trifluoro- 1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid (compound A) to give (Z)-(l R)-czs-3-(2-chloro- 3,3,3-trifluoro-l-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride (compound B) and b) esterifying (Z)-(lR)-czs-3-(2-chloro-3,3,3-trifluoro- 1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride (compound B) with the (2,3,5,6- tetrafluoro-4-methylphenyl)methanol (compound C) (see diagramm). (Z)-(IR)- cz5-3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid (compound A) is a known compound and its preparation is described for example in patent publication os. US4,683,089, WO02/06202, WO97/03941 and WO/9942432. (2,3,5,6-tetrafluoro-4- methylphenyl)methanol (C) is a known compound and its preparation is described for example in patent publication nos. US 4,370,346, WO02/034706 and WO02/034707.

Accordingly, the compound (I) may be produced as outlined in the below reaction scheme:

Step a) is performed by standard techniques as in 'March 4th Edition - p .437- 38'. Preferred chlorinating agents are thionyl chloride, phosgene or phosphorous oxychloride. Preferred solvents are hydrocarbons such as toluene, hexane, heptane or fluorobenzene. Preferred temperatures are from ambient to 100 °C or the boiling point of the solvent.

Step b) is performed in the presence of a solvent or in the absence of a solvent, in which case the molten product can act as the reaction medium. The reaction can be carried out in a single organic phase or in a mixture of a water immiscible organic phase and an aqueous phase. The acid chloride, either neat or in a solvent, may be added to the (2,3,5,6-tetraf3uoro-4- methylphenyl)methanol, or the vice versa, but it is preferable to add the acid chloride to the (2,3,5,6-tetrafluoro-4-methylphenyl)methanol. The moi ratio of the reactants is preferably 1:1 but up to 0 mol % excess of either reactant can be employed, but most preferably the excess of one reactant over the other is 1-5 mol%.

The reaction sequence can be performed step-wise, e.g. with isolation of the acid-chloride (B) prior to reaction with compound (C), but overall the compound (I) may also be prepared by a one-pot process, e.g. without isolation of the intermediates. The present invention relates therefore in one aspect to pesticidal mixtures comprising as active compounds 1) A compound (I) which is 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(lR)-czs-3- (2-chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate, preferably substantially free of any other isomer of 2,3,5,6-tetrafluoro-4- methylbenzyl 3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2- dimethylcyclopropanecarboxylate and

2) one or more further active ingredients (II) selected among compounds having insecticidal, nematicidal and/or acaricidal activity, e.g. selected from the following subgroups (1) to (29) (according to IRAC Mode-Of-Action classification): (1) Acetylcholinesterase (AChE) inhibitors e.g. such as alanycarb, , , benfuracarb, butocarboxim, butoxycarboxim, , , carbosulfan, ethiofencarb, , formetanate, furathiocarb, isoprocarb, methiocarb, , metolcarb, , pirimicarb, , thiodicarb, thiofanox, triazamate, trimethacarb, XMC, and xylylcarb; or organophosphates such as , , azinphos (-methyl, -ethyl), cadusafos, , , chlorfenvinphos, chlormephos, (-methyl), , cyanophos, demeton-S-methyl, , /DDVP, , , dimethylvinphos, , EPN, , , famphur, , , , fosthiazate, heptenophos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, , , mecarbam, , , , , , , oxydemeton- methyl, (-methyl), , , , , phosphamidon, , pirimi-phos (-methyl), profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, , sulfotep, , temephos, , , thiometon, triazophos, triclorfon, and vamidothion; (2) GABA-gated chloride channel antagonists e.g. Organochlorines such as , (alpha-); or fiproles (phenylpyrazoles) such as ethiprole, , pyrafluprole, and ; (3) Sodium channel modulators/voltage-dependent sodium channel blockers e.g. such as , allethrin (d-cis-trans, d-trans), , , bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, (beta-), (gamma-, lambda-), (alpha-, beta-, theta-, zeta-), [(lR)-trans- isomers], , dimefluthrin, [(EZ)-(lR)-isomers), , , , , flucythrinate, , fluvalinate (tau-), halfenprox, , , , [(lR)-trans-isomer), , profluthrin, (), , RU 15525, , [(lR)-isomers)], , and ZXI 8901; or DDT; or ; (4) Nicotinergic acetylcholine receptor agonists e.g. Chloronicotinyls such as , , , , , , ; or ; (5) Allosteric acetylcholine receptor modulators (agonists) e.g. spinetoram and ; (6) Chloride channel activators e.g. the avermectins/milbemycins including abamectin, aversectin C, doramectin, emamectin(-benzoate), eprinomectin, ivermectin, lepimectin, selamectin, moxidectin and milbemectin; (7) Juvenile hormone mimics e.g. , kinoprene, , or ; (8) gassing agents including methyl bromide and other alkyl halides; or chloropicrin; sulfuryl fluoride; borax; tartar emetic; (9) Selective homopteran feeding blockers such as pymetrozine or flonicamid; (10) Mite growth inhibitors e.g. lofentezine, diflovidazin, hexythiazox, etoxazole; ( 11) Microbial disruptors of 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, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Abl; (12) Inhibitors of mitochondrial ATP synthase e.g. diafenthiuron; or organotin miticides such as azocyclotin, cyhexatin, and fenbutatin oxide; or propargite; ; (13) Uncouplers of oxidative phoshorylation via disruption of the proton gradient including , and DNOC; (14) Nicotinic acetylcholine receptor channel blockers such as bensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium; (15) Inhibitors of chitin biosynthesis, type 0, e.g. such as bistrifluron, chlorfluazuron, , flucycloxuron, , hexaflumuron, , novaluron, noviflumuron, penfluron, teflubenzuron, and triflumuron; (16) Inhibitors of chitin biosynthesis, type 1 e.g. ; (17) Moulting disruptors e.g. ; (18) Ecdysone receptor agonists/disruptors e.g. Diacylhydrazines such as chromafenozide, halofenozide, methoxyfenozide, and ; (19) Octopamine receptor agonists e.g. ; (20) Mitochondrial complex III electron transport inhibitors e.g. , acequinocyl or fluacrypyrim; (21) Mitochondrial complex I electron transport inhibitors e.g. METI acaricides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, , tolfenpyrad or rotenone (Derris); (22)Voltage-dependent sodium channel blockers e.g. or ; (23) Inhibitors of acetyl CoA carboxylase e.g. Tetronic acid derivatives such as spirodiclofen and spiromesifen; or tetramic acid derivatives such as spirotetramat; (24) Mitochondrial complex IV electron inhibitors e.g. Phosphines such as , calcium phosphide, phosphine, and zinc phosphide or cyanide; (25) Mitochondrial complex II electron transport inhibitors e.g. Cyenopyrafen; (28) receptor modulators e.g. diamides such as , (Rynaxypyr), (Cyazypyr), 3-bromo-N- (2-bromo-4-chloro-6-[(l-cyclopropylethyl) carbamoyl]phenyl}-l-(3- chloropyridin-2-yl)-lH-pyrazole-5-carboxamide and methyl 2-[3,5- dibromo-2-({[3-bromo-l-(3-chloropyridin-2-0-lH-pyrazol-5- yl]carbonyl }amino)benzoyl]- 1,2-dimethylhydrazinecarboxylate; (29) , amidoflumet, benzoximate, bifenazate, chinomethionat, cryolite, cyflumetofen, , fluensulfone (5-chloro-2-[(3,4,4- trifluorobut-3-en-l-yl)sulfonyl]-l,3-thiazole), flufenerim, pyridalyl, and pyrifluquinazon; in synergistically effective amounts.

Especially preferred are mixtures comprising compounds selected among Acetylcholinesterase (AChE) inhibitors; Nicotinergic acetylcholine receptor agonists; Nicotinic acetyl-choline receptor allosteric activators; Chloride channel activators; Selective homopteran feeding blockers; Inhibitors of acetyl CoA carboxylase; and Ryanodine receptor modulators.

In a preferred embodiment the invention relates to pesticidal mixtures comprising as active compounds 1) A compound (I) which is 2-methylbiphenyl-3-ylmethyl (Z)-(\R)-cis-3-(2- chloro-3,3,3-trifluoroprop-l-enyl)-2,2-dimethylcyclopropanecarboxylate, preferably substantially free of any other isomer of 2-methylbiphenyl-3- ylmethyl (\RS)-3 -(2-chloro-3 ,3,3-trifluoroprop- 1-enyl)-2,2-dimethylcy clopro- panecarboxylate and

2) one or more further active ingredients (II) selected from the group consisting of abamectin, acequinocyl, acephate, acetamiprid, acrinathrin, afidopyraben, alanycarb, albendazole, aldicarb, allethrin, a/^/za-cypermethrin, aluminium phosphide, amitraz, azadirachtin, azamethiphos, azinphos-ethyl, azocyclotin, Bacillusfirmus, Bacillus sphaericus, i r z / thuringiensis (including susp.), bendiocarb, benfuracarb, bensultap, benzoximate, bephenium, betacyfluthrin, ^eto-cypermethrin, bifenazate, bifenthrin, resolved-bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethnn, bistrifluron, borax, BPMC, brofenprox, bromophos, bromopropylate, brotianide, bufencarb, buprofezin, butamisole, butocarboxim, butoxycarboxim, butylpyridaben, cadusafos, calcium phosphide, cambendazole, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap hydrochloride , chinomethionat, chloethocarb, chlorantraniliprole, chlordane, chlorfenapyr, chloroethoxyfos, chlorofenvinphos, chlorofluazuron, chloromephos, chloropicrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, cis-resmethrin, clocythrin, clofentezine, clorsulon, closantel, clothianidin, cryolite, coumaphos, cyanide, cyantraniliprole, cyanophos, cyclaniliprole, cycloprothrin, cyenopyrafen, cyflumetofen, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyphenothrin, cyromazine, d-cis-trans allethrin, deltamethrin, DDT, demeton-S-methyl, diafenthiuron, diamphenethide, dibromosalan, dichlorophen, 1,3-dichloroprene, difenthiuron, diazinon, dichlofenthion, dichlorvos, dicliphos, dicofol, dicrotophos, diethion, diethylcarbamazine, diflovidazin, diflubenzuron, dimethoate, dimethyl disulphide, dimethylvinphos, dinotefuran, , disulfoton, DNOC, d- trans allethrin, edifenphos, endosulfan, emamectin(-benzoate), empenthrin, EPN, epsiprantel, esfenvalerate, ethiofencarb, ethion, ethiprole, ethofenprox, ethoprop, ethoprophos, etoxazole, etrimphos, famphur, febantel, fenamiphos, fenbendazole, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazuron, flubendazole, flubendiamide, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, flufiprole, flumethrin, fluopyram, fluvalinate, flupyradifurone, fonophos, formetanate, formothion, fosthiazate, fubfenprox, furathiocarb, furfural, gamma-cyhalothrin, halfenprox, halofenozide, haloxon, heptafluthrin, heptenophos, Heterorhabtlitis bacteriophora, hexaflumuron, hexachlorophene, hexythiazox, hydramethylnon, hydroprene, imicyafos, imidacloprid, imiprothrin, indoxacarb, iprobenfos, isazophos, isofenfox, isofenphos, isoprocarb, isopropyl- O-salicylate, isoxathion, ivermectin, kadethrin, kinoprene, lambda-cyhalothrin, lepimectin, levamisole, lufenuron, malathion, mebendazole, mecarbam, mevinphos, mesulfenphos, metaflumizone, metaldehyde, metam sodium, metam potassium, methacrifos, methamidophos, methidathion, methiocarb, methomyl, methoxychlor, methoxyfenozide, methyl bromide, methyridine, metolcarb, mevinphos, milbemectin, momfluorothrin, monocrotophos, morantel, Myrothecium verrucaria strains, naled, netobimin, niclopholan, niclosamide, nicotine, nitenpyram, nitroxynil, novaluron, noviflumuron, omethoate, oxamyl, oxfendazole, oxibendazole, oxyclozanide, oxydemethon-M, oxydeprofos, parathion A, parathion M, parbendazol, Pasteuria spp., permethrin, phenothiazine, phenothrin, phenthoate, phorate, phosalone, phosmet, phosphorodithioate, phosphamidon, phosphine, phostebupirim, phoxim, piperonyl butoxide, pirimicarb, pirimiphos-methyl, prallethrin, praziquantel, profenofos, promecarb, propargite, propaphos, propetamphos, propoxur, prothiofos, prothoate, pyflubumide, pymetrozine, pyrachlophos, pyrantel, pyridalyl, pyridaphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxyfen, quinalphos, rafoxanide, resmethrin, ronnel, rotenone, dioxabenzophos (salithion), Saponins of Quillaja saponaria, sebufos, silafluofen, spinosad, spinetoram, spirodiclofen, spiromesifen, spirotetratmat, Steinernema scapterisci strains, Steinernemafeltiae, Steninernema kraussei, sulfotep, sulfoxaflor, sulfuramid, sulfuryl floride, sulprofos, tasmanone, tatar emetic, tow-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, temephos, terbam, terbufos, tetradifon, tetra-chlorvinphos, tetramethrin, tetramisole, thenium, t/Wa-cypermethrin, thiabendazole, thiacloprid, thiafenox, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiomethon, thionazin, thiophanate, thiosultap-sodium, thuringiensin, tolfenpyrad, tralomethrin, transfluthrin, triarathen, triazamate, triazophos, triazuron, trichlorfon, triclabendazole, triflumuron, trimethacarb, vamidothion, XMC, xylylcarb, zeto-cypermethrin, zinc phosphide, Bacillus firmus, Bacillus sphaericus, i r z / thuringiensis (including susp.), Heterorhabtlitis bacteriophora, Myrothecium verrucaria strains, Pasteuria spp., Saponins of Quillaja saponaria, Steinernema scapterisci strains, and Steinernemafeltiae, Steninernema kraussei; in synergistically effective amounts.

Table 1: mixtures of particular interest: I + aldicarb I + alanycarb I + nitenpyram I + thiacloprid I + benfuracarb I + carbaryl I + thiamethoxam I + spinosad I + butocarboxim I + butoxycarboxim I + spinetoram I + abamectin I + carbofuran I + carbosulfan I + emamectin benzo. I + ipimectin I + formetanate I + triazamate I + milbemectin I + lepimectin I + methiocarb I + methomyl I + kinoprene I + hydroprene I + oxamyl I + primicarb I + pyriproxyfen I + fenoxycarb I + propoxur I + thiodicarb I + fenbutatin oxide I + diafenthiuron I + acephate I + azamethiphos I + chlorfenapyr I + propargite I + azinphos-ethyl I + azinphos-methyl I + diflubenzuron I + bistrifluron I + chlorfenvinphos I + chlorpyrifos I + hexaflumuron I + flufenoxuron I + chlorpyrifos-Me I + demeton-S-Me I + novaluron I + lufenuron I + coumaphos I + ethoprophos I + chlorfluazuron I + flucycloxuron I + diazinon I + dichlorvos I + noviflumuron I + triflumuron I + dicrotophos I + dimethoate I + penfluron I + teflubenzuron I + disulfoton I + ethion I + halofenozide I + methoxyfenozide I + EPN I + famphur I + azadirachtin I + tebufenozide I + imicyafos I + isopropyl-O-salic. I + tolfenpyrad I + pyridaben I + fenitrothion I + fenthion I + fanazaquin I + fenpyroximate I + isoxathion I + malathion I + tebufenpyrad I + pyrimidin I + methamidaphos I + methidathion I + indoxacarb I + flufenerim I + mevinphos I + monocrotophos I + spirodiclofen I + metaflumizone I + oxymethoate I + oxydemeton-Me I + spirotetramat I + spiromesifen I + parathion I + parathion-Me I + amitraz I + amidoflumet I + phenthoate I + phorate I + clofentezine I + bifenazate I + phosalone I + phosmet I + cyflumetofen I + cyenopyrafen I + phosphamidon I + pirimiphos-Me I + flonicamid I + etoxazole I + quinalphos I + terbufos I + flupyrazophos I + flubendiamine I + tetra-chlorvinphos I + triazophos I + piperonyl butoxide I + hexythiazox I + trichlorfon I + acetoprole I + pyridalyl I + pymetrozine I + propetamphos I +chlordane I + chlorantraniliprole I + pyrifluquinazon I + ethiprole I + fipronil I + acequinocyl I + Al-phosphide I + pyrafluprole I + pyriprole I + benzoximate I + borax I + vaniliprole I + allethrin I + calcium phosphide I + chinomethionate I + gamma-cyhalothrin I + cyfluthrin I + chloroethoxyfos I + cryolite I + lambda-cyhalothrin I + cypermethrin I + cyantraniliprole I + cyclaniliprole I + alpha-cypermethrin I + beta-cypermethrin I + flufiprole I + flubendiamide I + zeta-cypermethrin I + deltamethrin I + DDT I + dicofol I + esfenvalerate I + etofenprox I + diflovidazin I +DNOC I + fenpropathrin I + fenvalerate I + furfural I + fluacrypyrim I + flucythrinate I + tau-fluvalinate I + hydramethylnon I + methoxychlor I + permethrin I + silafluofen I + methyl bromide I + phosphine I + bioallethrin I + d-cis-tra. allethrin I + rotenone I + dioxabenzofos I + d-trans allethrin I + resmethrin I + sulfoxaflor I + sulfuryl fluoride I + bioresmethrin I + cyphenothrin I + tetradifon I + flometoquin I + -cypermethrin I + flumethrin I + pyflubumide I + afidopyraben I + empenthrin I + imiprothrin I + tasmanone I + flupyradifurone I + halfenprox I + phenothrin I + bifenthrin I + Bacillus sphaericus I + kadethrin I + tetramethrin I + Bacillusfirmus I + Heterorhabtlitis bacteriophora I + prallethrin I + transfluthrin I + Bacillus I + Pasteuria spp. thuringiensis I + heptafluthrin I + momfluorothrin I + Myrothecium I + Steinernema verrucaria strains scapterisci strains I + tralomethrin I + nicotine I + Saponins of Quillaja I + Steninernema saponaria kraussei I + cartap I + thiocyclam I + dinotefuran I + Steinernema feltiae I + acetamiprid I + chlothianidin I + imidacloprid I + chloropicrini I + chlorethoxyfos I + ethoprop I + isofenfox I + temephos I + naled I + oxydeprofos I + phostebupirim I + phoxim I + profenofos I + ronnel

More preferred are the combinations of the compound (I) with one or more compounds selected among: Organophosphates such as 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- (methoxyaminothio-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 - and especially selected among chlorpyrifos, chlorpyrifos-methyl, dimethoate or malathion; Phenylpyrazoles such as ethiprole, fipronil, pyrafluprole, and pyriprole - and especially fipronil or ethiprole; Pyrethroids such as 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 [(lR)-trans-isomers], deltamethrin, dimefluthrin, empenthrin [(EZ)-(lR)-isomers), esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (tau-), halfenprox, imiprothrin, metofluthrin, permethrin, phenothrin [(lR)-trans- isomer), prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tetramethrin [(lR)-isomers)], tralomethrin, transfluthrin - and especially selected among bifenthrin, deltamethrin, lambda-cyhalothrin, and gamma- cyhalothrin; Chloronicotinyls such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam - and especially selected among acetamiprid, imidacloprid, thiacloprid and thiamethoxam; Avermectins such as abamectin, aversectin C, doramectin, emamectin(-benzoate), eprinomectin, ivermectin, lepimectin and selamectin - especially selected among abamectin and emmamectin-benzoate; Diacylhydrazines such as chromafenozide, halofenozide, methoxyfenozide, and tebufenozide - and especially methoxyfenozide; Spinosyns - especially selected among spinosad and spinetoram; Juvenile hormone mimics such as hydroprene, kinoprene, methoprene, fenoxycarb or pyriproxyfen - and especially pyriproxyfen; Benzoylureas especially selected among bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron and triflumuron - especially selected among lufenuron and novaluron; and Ryanodine receptor modulators especially selected among flubendiamide, chlorantraniliprole and cyantraniliprole.

Especially preferred are combinations comprising compound(s) (II) selected among Organophosphates, Phenylpyrazoles, Pyrethroids, Chloronicotinyls, Avermectins, Spinosyns, and Diamides; and especially the compounds chlorpyrifos, chlorpyrifos-methyl, fipronil, deltamethrin, lambda-cyhalothrin, gamma-cyhalothrin, bifenthrin, acetamiprid, imidacloprid, thiacloprid, thiamethoxam, abamectin, spinosad, spinetoram, chlorantraniliprole, cyanantraniliprole and flubendiamide.

The present invention also provides methods and uses for the control of insects, arachnids or nematodes comprising the exposure of the insect, arachnid, or nematode or their food supply, habitat, breeding grounds or their locus with a pesticidally effective amount of mixtures of the active compound I with at least one active compound II.

The mixtures of the active compounds I and II, or the active compounds I and II used simultaneously, that is jointly or separately, exhibit outstanding action against pests from the following orders: Insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lamb- dina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis, beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blasto- phagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Diabrotica longicornis, Diabrotica semipunctata, Diabrotica 12-punctata Diabrotica speciosa, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, lps typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria, flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza riorum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa thrips (Thysanoptera), e.g. Dichromothrips corbetti, Dichromothrips ssp., Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci, termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes grassei, Termes natalensis, and Coptotermes formosanus, cockroaches (Blattaria-Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis, bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas (Hemiptera), e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzus persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, Viteus vitifolii, Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., and Arilus critatus. ants, , wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex califomicus, Pheidole megacephala, Dasymutilla occidentalis, Bombus spp., Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile, crickets, grasshoppers, locusts (), e.g. Acheta domestica, , Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, and Locustana pardalina, arachnoidea, such as arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Ambryomma maculatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Dermacentor andersoni, Dermacentor variabilis, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Ornithodorus moubata, Ornithodorus hermsi, Ornithodorus turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyl- locoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kan- zawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and Oligonychus pratensis; Araneida, e.g. Latrodectus mactans, and Loxosceles reclusa, fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, silverfish, firebrat (Thysanura), e.g. Lepisma saccharina and Thermobia domestica, centipedes (Chilopoda), e.g. Scutigera coleoptrata, millipedes (Diplopoda), e.g. Narceus spp., earwigs (Dermaptera), e.g. forficula auricularia, lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus. Plant parasitic nematodes such as root-knot nematodes, Meloidogyne arenaria, Meloidogyne chitwoodi, Meloidogyne exigua, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica and other Meloidogyne species; cyst nematodes, Globodera rostochiensis, Globodera pallida, Globodera tabacum and other Globodera species, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; seed gall nematodes, Anguina funesta, Anguina tritici and other Anguina species; stem and foliar nematodes, Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi and other Aphelenchoides species; sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; ring nematodes, Criconema species, Criconemella species, Criconemoides species, and Mesocriconema species; stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus and other Ditylenchus species; awl nematodes, Dolichodorus species; spiral nematodes, Helicotylenchus dihystera, Helicotylenchus multicinctus and other Helicotylenchus species, Rotylenchus robustus and other Rotylenchus species; sheath nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; lance nematodes, Hoplolaimus columbus, Hoplolaimus galeatus and other Hoplolaimus species; false root-knot nematodes, Nacobbus aberrans and other Nacobbus species; needle nematodes, Longidorus elongates and other Longidorus species; pin nematodes, Paratylenchus species; lesion nematodes, Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus curvitatus, Pratylenchus goodeyi, Pratylencus neglectus, Pratylenchus penetrans, Pratylenchus scribneri, Pratylenchus vulnus, Pratylenchus zeae and other Pratylenchus species; Radinaphelenchus cocophilus and other Radinaphelenchus species; burrowing nematodes, Radopholus similis and other Radopholus species; reniform nematodes, Rotylenchulus reniformis and other Rotylenchulus species; Scutellonema species; stubby root nematodes, Trichodorus primitivus and other Trichodorus species; Paratrichodorus minor and other Paratrichodorus species; stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species and Merlinius species; citrus nematodes, Tylenchulus semipenetrans and other Tylenchulus species; dagger nematodes, Xiphinema americanum, Xiphinema index, Xiphinema diversicaudatum and other Xiphinema species; and other plant parasitic nematode species.

In a second aspect of the invention, there are provided pesticidal mixtures comprising as active compounds

1) A compound (I) which is 2-methylbiphenyl-3-ylmethyl (Z)-(lR)-cis-3-(2- chloro-3,3,3-trifluoroprop-l-enyl)-2,2-dimethylcyclopropanecarboxylate, preferably substantially free of any other isomer of 2-methylbiphenyl-3- ylmethyl ( RS -3-(2-chloro-3 ,3,3-trifluoroprop- 1-enyl)-2,2-dimethylcy clopro- panecarboxylate and

2) at least one fungicidal compound (II) selected from the following

II. 1) methyl benzimidazole (MBC) fungicides;

11.2) dicarboximide fungicides;

11. 3) demethylation inhibitor (DMI) fungicides; II.4) phenylamide fungicides; II. 5) amine/morpholine fungicides; II. 6) phospholipid biosynthesis inhibitor fungicides; II. 7) carboxamide fungicides; II. 8) hydroxy(2-amino-)pyrimidine fungicides; II. ) anilinopyrimidine fungicides; 11.10) N-phenyl carbamate fungicides;

II. 11) quinone outside inhibitor (Qol) fungicides; 11.12) phenylpyrrole fungicides; 11.13) quinoline fungicides; II. 14) lipid peroxidation inhibitor fungicides; II. 15) melanin biosynthesis inhibitors-reductase (MBI-R) fungicides; melanin biosynthesis inhibitors-dehydratase (MBI-D) fungicides; hydroxyanilide fungicides; squalene-epoxidase inhibitor fungicides; polyoxin fungicides; phenylurea fungicides; quinone inside inhibitor (Qil) fungicides; benzamide fungicides; enopyranuronic acid antibiotic fungicides; hexopyranosyl antibiotic fungicides; glucopyranosyl antibiotic: protein synthesis fungicides; glucopyranosyl antibiotic: trehalase and inositol biosynthesis fungicides; cyanoacetamideoxime fungicides; carbamate fungicides; oxidative phosphorylation uncoupling fungicides; organo tin fungicides; carboxylic acid fungicides; heteroaromatic fungicides; phosphonate fungicides; phthalamic acid fungicides; benzotriazine fungicides; benzene-sulfonamide fungicides; pyridazinone fungicides; thiophene-carboxamide fungicides; pyrimidinamide fungicides; carboxylic acid amide (CAA) fungicides; tetracycline antibiotic fungicides; thiocarbamate fungicides; benzamide fungicides; host plant defense induction fungicides; multi-site contact activity fungicides; ergistically effective amount. In particular the at least one fungicidal compound (II) is selected from the following groups: A) azoles, in particular: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flutriafol, flusilazole, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, penconazole, propiconazole, prothioconazole, pyrisoxazole, simeconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamid, benomyl, carbendazim, thiabendazole, fuberidazole, ethaboxam, etridiazole, hymexazole; B) strobilurins, in particular: azoxystrobin, benzothiostrobin, coumethoxystrobin, coumoxystrobin, enoxastrobin, dimoxystrobin, fenaminstrobin, flufenoxystrobin, enestrobunn, fluoxastrobin, kresoxim-methyl, mandestrobin, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, tnfloxystrobin, pyrametostrobin, pyriministrobin, triclopyricarb, pyraoxystrobin, fenamidone, famoxadone, or pyribencarb; C) carboxamides, in particular: carboxin, benalaxyl, benodanil, boscalid, fenfuram, fenhexamid, fenpyrazamine, flutolanil, furalaxyl, furametpyr, isofetamid, isotranil, kiralaxyl, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, pyrimorph, thifluzamide, tiadinil, bixafen, dimethomorph, flumorph, flumetover, fluopicolide (picobenzamid), zoxamide, carpropamid, diclocymet, mandipropamid, isopyrazam, fluxapyroxad, sedaxane, penflufen, fluopyram; D) heterocylic compounds, in particular: benzovindiflupyr, fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil, triforine, fenpiclonil, fludioxonil, aldimorph, chloozolinate, dimethirimol, dodemorph, ethirimol, fenpropimorph, tridemorph, fenpropidin, iprodione, piperalin. procymidone, vinclozolin, famoxadone, fenamidone, octhilinone, probenazole, pyrisoxazole, amisulbrom, anilazine, diclomezine, pyroquilon, proquinazid, tricyclazole, acibenzolar-S-methyl, captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen; E) carbamates, in particular: mancozeb, maneb, metam, metiram, ferbam, propineb, thiram, zineb, ziram, benthiavalicarb, diethofencarb, iodocarb, iprovalicarb, flubenthiavalicarb, methasulfocarb, propamocarb, prothiocarb, pyributicarb, valifenalate; and F) other active compounds, selected from guanidines: dodine, iminoctadine and guazatine; antibiotics: blasticidin-S, kasugamycin, streptomycin, oxytetracycline, polyoxin and validamycin; nitrophenyl derivates: binapacryl, dinocap, dinobuton and meptyldinocap; sulfur-containing heterocyclyl compounds: dithianon and isoprothiolane; organometal compounds: fentin salts, such as fentin-acetate, chloride or hydroxide; organophosphorus compounds: edifenphos, iprobenfos, fosetyl, fosetyl-AL, phosphorous acid and its salts, pyrazophos and tolclofos-methyl; organochlorine compounds: biphenyl, chloroneb, dicloran, chlorothalonil, dichlofluanid, flusulfamide, hexachlorobenzene, phthalide, pencycuron, quintozene, tecnazene, thiophanate- methyl and tolylfluanid; inorganic active compounds: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate and sulfur; others: cyflufenamid, cymoxanil, dimethirimol, ethirimol, furalaxyl, metrafenone, flutianil, pyriofenone, bupirimate, oxathiapiprolin and spiroxamine; Bacillus spp.: B. subtilis and B amyloliquefaciens; plant extracts: alternifolia; in a synergistically effective amount.

The synergistic effect provided is both in respect of insecticidal, acaricidal, nematicidal effect and fungicidal effect.

Table 2 : Mixtures of particular interest:

I + bitertanol I + bromuconazole I + isopyrazam I + fluxapyroxad I + cyproconazole I + difenoconazole I + sedaxane I + penflufen I + diniconazole I + enilconazole I + flumetover I + penflufen I + epoxiconazole I + fluquinconazole I + fluopyram I + benzovindiflupyr I + fenbuconazole I + flusilazole I + fluazinam I + pyrifenox I + flutriafol I + hexaconazole I + cyprodinil I + fenarimol I + imibenconazole I + ipconazole I + ferimzone I + mepanipyrim I + metconazole I + myclobutanil I + nuarimol I + pyrimethanil I + penconazole I + propiconazole I + triforine I + fenpiclonil I + prothioconazole I + simeconazole I + fludioxonil I + aldimorph I + oxpoconazole I + pyrisoxazole I + dodemorph I + fenpropimorph I + triadimefon I + triadimenol I + tridemoφ h I + fenpropidin I + tebuconazole I + tetraconazole I + iprodione I + procymidone I + triticonazole I + prochloraz I + vinclozolin; I + famoxadone I + pefurazoate I + imazalil I + fenamidone I + octhilinone I + triflumizole I + cyazofamid I + probenazole; I + amisulbrom I + benomyl I + carbendazim I + anilazine I + diclomezine I + thiabendazole I + fuberidazole I + pyroquilon I + proquinazid I + ethaboxam I + etridiazole I + tricyclazole I + acibenzolar-S-Me I + hymexazole I + azoxystrobin I + captafol I + captan I + dimoxystrobin I + enestroburin I + dazomet I + folpet I + fluoxastrobin I + kresoxim-methyl I + fenoxanil I + quinoxyfen I + metominostrobin I + orysastrobin I + bupirimate I + chloozolinate I + picoxystrobin I + pyraclostrobin I + dimethirimol I + ethirimol I + benzothiostrobin I + coumethoxystrobin I + piperalin I + pyrisoxazole I + coumoxystrobin I + enoxastrobin I + mancozeb I + maneb I + fenaminstrobin I + flufenoxystrobin I + metam I + metiram I + mandestrobin I + pyrametostrobin I + ferbam I + propineb I + pyriministrobin I + triclopyricarb I + thiram I + zineb I + pyraoxystrobin I + fenamidone I + ziram I + diethofencarb I + famoxadone I + pyribencarb I + iprovalicarb I + flubenthiavalicarb I + trifloxystrobin I + carboxin I + benthiavalicarb I + iodocarb I + benalaxyl I + boscalid I + methasulfocarb I + prothiocarb I + fenhexamid I + flutolanil I + pyributicarb I + valifenalate I + furametpyr I + mepronil I + Propamocarb I + dodine I + metalaxyl I + mefenoxam I + iminoctadine I + benthiavalicarb I + ofurace I + oxadixyl I + streptomycin I + polyoxine I + oxycarboxin I + penthiopyrad I + binapacryl I + dinocap I + thifluzamide I + tiadinil I + dinobuton I + dithianon I + dimethomorph I + flumoφ h I + isoprothiolane I + fentin-acetate I + fluopicolid I + zoxamide I + edifenphos I + iprobenfos I + diclocymet I + mandipropamid I + fosetyl I + fosetyl-aluminum I + benodanil I + fenfuram I + phosphorous acid I + pyrazophos I + fenpyrazamine I + furalaxyl I + tolclofos-methyl I + chlorothalonil I + isofetamid I + isotranil I + dichlofluanid I + flusulfamide I + kiralaxyl I + pyrimorph I + hexachlorobenzene I + phthalide I + bixafen I + carpropamid I + pencycuron I + quintozene I + guazatine I + blasticidin-S I + thiophanate-methyl I + tolylfluanid I + kasugamycin I + oxytetracycline I + Bordeaux mixture I + copper acetate I + validamycin I + meptyldinocap I + copper hydroxide I + Cu-oxychloride I + biphenyl I + chloroneb I + copper sulfate I + cyflufenamid I + dicloran I + chlorothalonil I + cymoxanil I + dimethirimol I + dichlofluanid I + flusulfamide I + ethirimol I + flutianil I + tecnazene I + pyriofenone I + metrafenone I + spiroxamine I + bupirimate I + oxathiapiprolin The mixtures of a compound (I) and a compound (II) or the simultaneous, that is joint or separate, use of a compound (I) and a compound (II) are distinguished by being highly active against a wide range of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Peronosporomycetes and Basidiomycetes. The mixtures act systemically, translaminar or through contact and can be used in crop protection as foliar fungicides, as fungicides for seed dressing and as soil-acting fungicides.

Advantageously, the mixtures comprising one or more fungicides are suitable for controlling the following plant diseases: Albugo spp. (white rust) on ornamentals, vegetables (e.g. A . Candida) and sunflowers (e.g. A . tragopogonis), Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e.g. A . solani or A . alternata), tomatoes (e.g. A . solani or A . alternata) and wheat, Aphanomyces spp. on sugar beets and vegetables, Ascochyta species on cereals and vegetables, e.g. A . tritici (anthracnose) on wheat and A . hordei on barley, Bipolaris and Drechslera spp. (Teleomorph: Cochliobolus spp.) on corn (e.g. D . maydis), cereals (e.g. B . sorokiniana: spot blotch), rice (e.g. B . oryzae) and turfs, Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e.g. on wheat or barley), Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e.g. strawberries), vegetables (e.g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat, Bremia lactucae (downy mildew) on lettuce, Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e.g. C . ulmi (Dutch elm disease) on elms, Cercospora spp. (Cercospora leaf spots) on corn, rice, sugar beets (e. g . C . beticola), sugar cane, vegetables, coffee, soybeans (e.g. C . sojina or C . kikuchii) and rice, Cladosporium spp. on tomatoes (e.g. C . fulvum: leaf mold) and cereals, e.g. C . herba-rum (black ear) on wheat, Claviceps purpurea (ergot) on cereals, Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e.g. C . sativus, anamorph: B . sorokiniana) and rice (e.g. C . miy- abeanus, anamorph: H . oryzae), Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e.g. C . gossypii), corn (e.g. C . graminicola), soft fruits, potatoes (e.g. C . coccodes: black dot), beans (e.g. C . lindemuthianum) and soybeans (e.g. C . truncatum), Corticium spp., e.g. C . sasakii (sheath blight) on rice, Corynespora cassiicola (leaf spots) on soybeans and ornamentals, Cycloconium spp., e.g. C . oleaginum on olive trees, Cylindrocarpon spp. (e.g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e.g. C . liriodendri, teleomorph: Neonectria liriodendri: Black Foot Disease) and ornamentals, Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans, Diaporthe spp., e.g. D . phaseolorum (damping off) on soybeans, Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e.g. D . teres, net blotch) and wheat (e.g. D . tritici-repentis: tan spot), rice and turf, Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa, Elsinoe spp. on pome fruits (E. pyri), soft fruits (E. veneta: anthracnose) and vines (E. ampelina: anthracnose), Entyloma oryzae (leaf smut) on rice, Epicoccum spp. (black mold) on wheat, Erysiphe spp. (powdery mildew) on sugar beets (E. betae), vegetables (e.g. E . pisi), such as cucurbits (e.g. E . cichoracearum), cabbages, rape (e.g. E . cruciferarum), Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods, Exserohilum (syn. Helminthosporium) spp. on corn (e.g. E . turcicum), Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e.g. wheat or barley), F. oxysporum on tomatoes, F. solani on soybeans and F. verticillioides on corn, Gaeumannomyces graminis (take-all) on cereals (e.g. wheat or barley) and corn, Gibberella spp. on cereals (e.g. G . zeae) and rice (e.g. G . fujikuroi: Bakanae disease), Glomerella cingulata on vines, pome fruits and other plants and G . gossypii on cotton, Grainstaining complex on rice, Guignardia bidwellii (black rot) on vines, Gymno sporangium spp. on rosaceous plants and junipers, e.g. G . sabinae (rust) on pears, Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice, Hemileia spp., e.g. Hemileia vastatrix (coffee leaf rust) on coffee, lsariopsis clavispora (syn. Cladosporium vitis) on vines, Macrophomina phaseolina (syn. phaseoli) (root and stem rot) on soybeans and cotton, Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e.g. wheat or barley), Microsphaera diffusa (powdery mildew) on soybeans, Monilinia spp., e.g. M . laxa, M . fructicola and M . fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants, Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e.g. M . graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M . fijiensis (black Sigatoka disease) on bananas, Peronospora spp. (downy mildew) on cabbage (e.g. P. brassicae), rape (e.g. P. parasitica), onions (e.g. P. destructor), tobacco (P. tabacina) and soybeans (e.g. P. manshurica), Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans, Phialophora spp. e.g. on vines (e.g. P. tracheiphila and P. tetraspora) and soybeans (e.g. P. gregata: stem rot), Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets, Phomopsis spp. on sunflowers, vines (e. g . P. viticola: can and leaf spot) and soybeans (e.g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum), Physorma maydis (brown spots) on corn, Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e.g. P. capsici), soybeans (e.g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e.g. P. infestans: late blight) and broad-leaved trees (e.g. P. ramorum: sudden oak death), Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants, Plasmopara spp., e.g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers, Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e.g. P. leucotricha on apples, Polymyxa spp., e.g. on cereals, such as barley and wheat (P. graminis) and sugar beets (P. betae) and thereby transmitted viral diseases, Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on cereals, e.g. wheat or barley, Pseudoperonospora (downy mildew) on various plants, e.g. P. cubensis on cucurbits or P. humili on hop, Pseudopezicula tracheiphila (red fire disease or rotbrenner', anamorph: Phialophora) on vines, Puccinia spp. (rusts) on various plants, e.g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e.g. wheat, barley or rye, and asparagus (e. g . P. asparagi), Pyrenophora (anamorph: Drechslera) tritici- repentis (tan spot) on wheat or P. teres (net blotch) on barley, Pyricularia spp., e.g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals, Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, sugar beets, vegetables and various other plants (e.g. P. ultimum or P. aphanidermatum), Ramularia spp., e.g. R . collocygni (Ramularia leaf spots, Physiological leaf spots) on barley and R . beticola on sugar beets, Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e.g. R . solani (root and stem rot) on soybeans, R . solani (sheath blight) on rice or R . cerealis (Rhizoctonia spring blight) on wheat or barley, Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes, Rhynchosporium secalis

(scald) on barley, rye and triticale, Sarocladium oryzae and S. attenuatum (sheath rot) on rice, Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e.g. S. sclerotiorum) and soybeans (e.g. S. rolfsii), Septoria spp. on various plants, e.g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora blotch) on cereals, Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines, Setospaeria spp. (leaf blight) on corn (e.g. S. turcicum, syn. Helminthosporium turcicum) and turf,

Sphacelotheca spp. (smut) on corn, (e.g. S. reiliana: head smut), sorghum und sugar cane, Sphaerotheca fuliginea (powdery mildew) on cucurbits, Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases, Stagonospora spp. on cereals, e.g. S. nodorum (Stagonospora blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat, Synchytrium endobioticum on potatoes (potato wart disease), Taphrina spp., e.g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums, Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e.g. T. basicola (syn. Chalara elegans), Tilletia spp. (common bunt or stinking smut) on cereals, such as e.g. T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat, Typhula incarnata (grey snow mold) on barley or wheat, Urocystis spp., e.g. U . occulta (stem smut) on rye, Uromyces spp. (rust) on vegetables, such as beans (e.g. U . appendiculatus, syn. U . phaseoli) and sugar beets (e.g. U . betae), Ustilago spp. (loose smut) on cereals (e.g. U . nuda und U . avaenae), corn (e.g. U . maydis: corn smut) and sugar cane, Venturia spp. (scab) on apples (e.g. V. inaequalis) and pears, Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e.g. V. dahliae on strawberries, rape, potatoes and tomatoes.

The mixtures of the compound (I) and active compounds (II), when compound (II) scomprise a fungicide, are furthermore suitable for controlling harmful pests in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products. In the protection of wood, particular attention is paid to the following harmful fungi: Ascomycetes, such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes, such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes, such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes, such as Mucor spp., additionally in the protection of materials the following yeasts: Candida spp. and Saccharomyces cerevisae. The mixtures according to the present invention can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compounds according to the invention.

The formulations are prepared in a known manner. By example and in particular for crop protection use, the formulations can be prepared by extending the active compound with auxiliaries suitable for the formulation of , such as solvents and/or carriers, if desired emulsifiers, surfactants and dispersants, preservatives, anti-foaming agents, anti-freezing agents, for seed treatment formulation also optionally gelling agents.

Examples of suitable solvents are water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones e.g. M P (N-methyl-pyrrolidone) and NOP (N-octyl-pyrrolidone), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used.

Suitable emulsifiers are nonionic, cationic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates).

Examples of dispersants are lignin-sulfite waste liquors and methylcellulose.

Suitable surfactants used are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalene-sulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.

Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water.

Also anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bactericides such as can be added to the formulation.

Suitable antifoaming agents are for example antifoaming agents based on silicon or magnesium stearate.

A suitable preservative is e.g. dichlorophen.

An example of a gelling agent is carrageen (Satiagel).

Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier. Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers.

Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compounds. In this case, the active compounds are employed in a purity of from 90% to 100% by weight, preferably 95% to 100% by weight (according to MR spectrum).

For seed treatment purposes, respective formulations can be diluted 2-10 fold leading to concentrations in the ready to use preparations of 0.01 to 60% by weight active compounds by weight, preferably 0.1 to 40% by weight.

The mixtures of the present invention can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, microcapsule suspensions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of the active compounds according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or 5 emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.

The active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, 10 preferably from 0.01 to 1 % per weight.

The active compounds may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply the active compound without 15 additives.

The following are examples of formulations:

1. Products for dilution. For seed treatment purposes, such products may be 20 applied to the seed diluted or undiluted.

A) Water-soluble concentrates (SL, LS) 10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other 2 5 auxiliaries are added. The active compound(s) dissolve(s) upon dilution with water, whereby a formulation with 10 % (w/w) of active compound(s) is obtained.

B) Dispersible concentrates (DC) 30 20 parts by weight of the active compound(s) are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion, whereby a formulation with 20% (w/w) of active compound(s) is obtained.

C) Emulsifiable concentrates (EC)

15 parts by weight of the active compound(s) are dissolved in 7 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion, whereby a formulation with 15% (w/w) of active compound(s) is obtained.

D) Emulsions (EW, EO, ES) 25 parts by weight of the active compound(s) are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w) of active compound(s) is obtained.

E) Suspensions (SC, OD, FS) In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants, wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the active compound(s), whereby a formulation with 20% (w/w) of active compound(s) is obtained.

F) Water-dispersible granules and water-soluble granules (WG, SG) 50 parts by weight of the active compound(s) are ground finely with addition of 50 parts by weight of dispersants and wetters and made as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluid- ized bed). Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 50% (w/w) of active compound(s) is obtained.

G) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS) 75 parts by weight of the active compound(s) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 75% (w/w) of active compound(s) is obtained.

H) Gel-Formulation (GF) In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants, 1 part by weight of gelling agent wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound) suspension. Dilution with water gives a stable suspension of the active compound(s), whereby a formulation with 20% (w/w) of active compound(s) is obtained.

2 . Products to be applied undiluted. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.

I) Dustable powders (DP, DS) 5 parts by weight of the active compound(s) are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having 5% (w/w) of active compound(s).

J) Granules (GR, FG, GG, MG) 0.5 part by weight of the active compound(s) is ground finely and associated with 95.5 parts by weight of carriers, whereby a formulation with 0.5% (w/w) of active compound(s) is obtained. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted for foliar use. K) ULV solutions (UL) 10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product having 10% (w/w) of active compound(s), which is applied undiluted for foliar use. L) Capsule supensions (CS)

2 8 parts of a combination of the compound(s), or of each of these compounds separately, are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture ( 8 : 1). This mixture is emulsified in a mixture of 1 .2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 5 1 .6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2 . 8 parts 1 , 6 -diaminohexane in 5 .3 parts of water is added. The mixture is agitated until the polymerization reaction is completed.

The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains

28% of the active ingredients. The medium capsule diameter is 3 - 1 0 microns.

Various types of oils, wetters, adjuvants, , fungicides, inseticides, nematicides, acaricides, other pesticides, and/or bactericides may be added to the active ingredients, if appropriate just immediately prior to use (tank mix). These agents usually are admixed with the agents according to the invention in a weight ratio of 1 :2 0 to 20: 1 .

Emulsifiable concentrates:

Active ingredient(s): 1 to 99°/ o, preferably 6 0 to 90%

Surfactant: 1 to 30°/ o, preferably 1 to 20%

Solvent: 1 to 80°/ o, preferably 1 to 3 5 %

Dusts:

Active ingredient(s): 0 . 1 to 90%, preferably 1 to 80%

Solid carrier: 1 to 99.9%, preferably 1 5 to 90% Suspension concentrates: Active ingredient(s): 5 to 75%, preferably 10 to 50% Water: 24 to 94%, preferably 30 to 88% Surfactant: 1 to 40%, preferably 2 to 30%

Suspo-emulsion

Active ingredient(s): 1 to 99%, preferably 10 to 50% Surfactant: 1 to 30%, preferably 1 to 20% Solvent 1 to 80%, preferably 1 to 35%

Wettable powders: Active ingredient(s): 0.1 to 90%, preferably 1 to 80% Surfactant: 1 to 50%, preferably 1 to 15%

Solid carrier: 1 to 95%, preferably 15 to 90%

Granulates: Active ingredient(s): 0.1 to 90%, preferably 1 to 80% Surfactant: 1 to 50%, preferably 1 to 15%

Solid carrier: 1 to 95%, preferably 15 to 90%

Suspension composition for seed treatment: Active ingredient(s): 0.1 to 90%, preferably 1 to 80% Surfactant: 1 to 40%, preferably 1 to 20% Solvent: 1 to 90%, preferably 1 to 50% Colorants: 0 to 40%, preferably 1 to 20% Binder: 0 to 60%, preferably 1 to 40%

The compound (I) and one or more compound(s) (II) can be applied simultaneously, that is jointly or separately, or in succession, the sequence, in the case of separate application, generally not having any effect on the result of the control measures. The mixtures of the present invention are employed as such or in form of compositions by treating the insects, arachnid, nematode, fungi or the plants (including crops), plant propagation materials such as seeds, part of the plant and/or plant organ that grow at a later point in time, water in which plants grow, soil, surfaces, materials or rooms to be protected from insecticidal acaricidal, nematicidal or insecticidal-/acaricidal-/nematicidal-fungicidal attack with an insecticidally, acaricidal, nematicidal or insecticidal-/acaricidal-/nematicidal- fungicidally effective amount of the active compounds. The application can be carried out both before and after the infection of the plants, plant propagation materials such as seeds, part of the plant and/or plant organ that grow at a later point in time, water in which plants grow, soil, surfaces, materials or rooms by the insects or harmful pests.

The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g . potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.

For crop use, the compound (I) and the one or more compound(s) (II) are usually applied in a weight ratio of from 1000:1 and 1:1000. In other embodiments that weight ratio of (I) to (II) may be between 500:1 to 1:500, for example between 100: 1 to 1:100, for example between 1:50 to 50:1, for example 1:20 to 20:1, for example 1:10 to 10:1, for example 1:5 to 5:1. Other examples of weight ratios of (I) to (II) include 1:1, 1:2, 1:3, 1:4, 2:1, 3:1, 4:1. The invention also provides pesticidal mixtures comprising a combination of components (I) and (II) as mentioned above in a synergistically effective amount, together with an agriculturally acceptable carrier, and optionally a surfactant. Depending on the desired effect, the specific mixture partner(s), pest to be controlled, crop to be protected and/or soil or weather condition, the application rates of the mixtures according to the invention are e.g. from 2 g/ha to 2000 g/ha, preferably from 5 to 1500 g/ha, in particular from 10 to 1000 g/ha. In a preferred embodiment the application rates of the mixtures are from 20-800 g/ha, preferably from 25-600 g/ha, and most preferably 50-500 g/ha.

In a preferred embodiment amounts applied of compound (I) and/or the at least one compound (II) is lower than the normal dose rate required to achieve the same effect/result had either of the actives been applied individually, i.e. the synergistic effect of the combination result in a lower dose rate of either or both (or more) compounds required to achieve the same or improve the effect.

The inventive mixtures and the compositions comprising them can be used for protecting materials (e.g. technical materials) e.g. wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling pests e.g. ants, flies, spiders, mosquitoes and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).

Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with the inventive mixtures and their respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like, insecticidal compositions for application to fibers, fabric, knitgoods, non-wovens, netting material or foils and tarpaulins preferably comprise a composition including the inventive mixtures, optionally a repellent and at least one binder.

According to a preferred embodiment of the invention, the mixtures according to the present invention are employed via direct or soil application. Soil application (incl. perimeter application) is especially favorable for use against ants, termites, crickets, or cockroaches as well as soilborne fungi.

According to another preferred embodiment of the invention, for use against non crop pests such as ants, termites, wasps, flies, mosquitoes, crickets, locusts, or cockroaches the mixtures according to the present invention are prepared into a bait preparation. The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). The bait employed in the composition is a product which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitoes, crickets etc. or cockroaches to eat it. This attractant may be chosen from feeding stimulants or para and/or sex pheromones readily known in the art. The mixtures according to the invention can be applied to any and all developmental stages, e.g. for insect control: egg, larva, pupa, and adult. The pests may be controlled by exposing the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of the inventive mixtures or of compositions comprising the mixtures. "Locus" means a plant, seed, soil, area, material or environment in which a pest is growing or may grow.

For non-crop use the compound (I) and the one or more compound(s) (II) are usually applied in a weight ratio of from 1000:1 to 1:1000 as well as those preferred ratios provided above for crop use. Depending on the desired effect, the specific mixture partner(s), pest to be controlled, material to be protected and/or weather condition the application rates of the mixtures according to the invention are usually from 1 - 150 g/L. Compositions of this invention may further contain other active ingredients than those listed above. For example herbicides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators and safeners. These additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix). For example, the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.

In general, pesticidally "effective amount" means the amount of the inventive mixtures or of compositions comprising the mixtures needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The effective amount can vary for the various mixtures/compositions used in the invention. An effective amount of the mixtures/compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.

In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient(s), by example, ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.

Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound(s) per m2 treated material, desirably from 0.1 g to 50 g per m2.

Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide. For use in bait compositions, the typical content of active ingredient(s) is from 0.0001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound. The composition used may also comprise other additives such as a solvent of the active material, a flavoring agent, a preserving agent, a dye or a bitter agent. Its attractiveness may also be enhanced by a special color, shape or texture.

For use in spray compositions, the content of the mixture of the active ingredients is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight % .

In the context of the present invention, the term plant refers to an entire plant, a part of the plant or the propagation material of the plant.

The mixtures of the present invention and the compositions comprising them are particularly important in the control of a multitude of insects and/or pests (e.g. fungi) on various cultivated plants, such as cereal, root crops, oil crops, vegetables- and fruit spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, coffee, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, grapewines, petunias, geranium/pelargoniums, pansies and impatiens.

Plants which can be treated with the inventive mixtures include all genetically modified plants or transgenic plants, e.g. crops which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods, or plants which have modified characteristics in comparison with existing plants, which can be generated for example by traditional breeding methods and/or the generation of mutants, or by recombinant procedures.

The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post- transtional modification of protein(s) (oligo- or polypeptides) for example by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties (e.g. as disclosed in Biotechnol. Prog. 2001 Jul-Aug. 17(4), 720-8; Protein Eng. Des. Sel. 2004 Jan. 17(1), 57-66; Nat. Protoc. 2007, 2(5), 1225-35; Curr. Opin. Chem. Biol. 2006 Oct 10(5), 487-91; Epub. 2006, Aug 28.; Biomaterials. 2001 Mar. 22(5), 405-17; Bioconjug. Chem. 2005 Jan-Feb. 16(1): 1 13-21).

The term "cultivated plants" is to be understood also including plants that have been rendered tolerant to applications of specific classes of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e.g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e.g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate- 3-phosphate synthase (EPSPS) inhibitors, such as glyphosate (see e.g. WO 92/00377); glutamine synthetase (GS) inhibitors, such as glufosinate (see e.g. EP-A-0242236, EP-A-242246) or oxynil herbicides (see e.g. US 5,559,024) or PPO herbicides, ACCase herbicides, 2,4-D and dicamba as a result of conventional methods of breeding or genetic engineering. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield summer rape (Canola) being tolerant to imidazolinones, e.g. imazamox. Genetic engineering methods have been used to render cultivated plants, such as soybean, cotton, corn, beets and rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercialy available under the trade names RoundupReady (glyphosate) and LibertyLink (glufosinate).

The term "cultivated plants" is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial Bacillus, particularly from Bacillus thuringiensis, such as a-endotoxins, e . g . CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bi) or Cry[theta]c; vegetative insecticidal proteins (VIP), e.g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp.; toxins produced by , such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific ; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxy steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, trun- cated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, for example WO 02/015701). Further examples of such toxins or genetically-modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 and WO 03/052073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins protection from harmful pests from certain taxonomic groups of , particularly to beetles (Coleoptera), flies (Diptera), and butterflies and moths (Lepidoptera) and to plant parasitic nematodes (Nematoda).

The term "cultivated plants" is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called " pathogenesis- related proteins" (PR proteins, see, for example EP-A 0 392 225), plant disease resistance genes (for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e.g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

The term "cultivated plants" is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, nitrogen utilization, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.

The term "cultivated plants" is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, for example oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g. Nexera rape). The term "cultivated plants" is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, for example potatoes that produce increased amounts of amylopectin (e.g. Amflora potato).

Some of the inventive mixtures have systemic action and can therefore be used for the protection of the plant shoot against foliar pests as well as for the treatment of the seed and roots against soil pests.

The mixtures according to the present invention are also suitable for the protection of plant propagation material including treatment of seeds in order to protect the seed from insect pest, in particular from soil-living insect pests; and/or fungi and the resulting plant's roots and shoots against soil pests and foliar insects and/or fungi. The protection of the resulting plant's roots and shoots is preferred.

More preferred is the protection of resulting plant's shoots from piercing and sucking insects.

The present invention therefore comprises a method for the protection of seeds from insects and fungi, in particular from soil insects and of the seedlings' roots and shoots from insects, in particular from soil and foliar insects, said method comprising contacting the seeds before sowing and/or after pre-germination with mixtures according to the present invention. Particularly preferred is a method, wherein the plant's roots and shoots are protected, more preferably a method, wherein the plants shoots are protected from piercing and sucking insects, most preferably a method, wherein the plants shoots are protected from such pests as aphids, spider mite, army worm, leaf hopper, European corn borer, cutworm, corn ear worm, corn root worm, stink bugs, plant bug, wireworm, codling moth, and navel orange worm.

The term seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like and means in a preferred embodiment true seeds. The application methods according to the invention for the protection of plant propagation material are characterized in that, for example, the composition are applied in such a manner that it is applied in close spatial proximity to, or spatially together with, planting or sowing the plant propagation material at the site of planting or sowing. Application of the composition in close spatial proximity to the site of planting or sowing takes place preferably when planting or sowing the plant propagation material, by applying the compositions by soil application directly to the site where the plant propagation material has been planted or sown, for example preferably when sowing into the seed furrow, or to a closely delimited area around the site of planting or sowing the plant propagation material. In addition, the mixture composition (compound (I) + (II)) will create a zone of protection in the soil, which controls the pests in the soil, but also the roots and stems, when contacted with the soil containing the composition, absorb the composition, and then distribute the composition throughout the plant through known means. Application of such compositions, which takes place spatially together with planting or applying the plant propagation material to the site of planting or sowing is to be understood as meaning that plant propagation material which has been pretreated with these compositions is planted or sown at the site of planting or sowing, it being possible, depending on the intended aims and prevailing circumstances, for the pretreatment of the plant propagation material to be affected for example by spraying, atomizing, dusting or scattering the compositions over the plant propagation material or brushing or pouring the compositions over the plant propagation material or, in the event of seed, in particular also by dressing the seed. When carrying out seed dressing, i.e. dry seed, wet seed-dressing, liquid seed-dressing or slurry dressing, mixture composition is added to the seed prior to sowing in a seed-dressing apparatus and the composition is distributed uniformly over the seed, for example by stirring the contents of the seed- dressing apparatus and/or by rotating and/or shaking the entire seed-dressing apparatus. Particular embodiments of such a seed-dressing treatment comprise, for example, immersing the seed in a liquid composition, coating the seed with a solid composition (seed coating) or by achieving penetration of the active ingredient into the seed by adding the composition to the water used for pre- soaking the seed (seed soaking). For a general discussion of techniques used to apply pesticides to seeds, see "Seed Treatment," 2d ed., (1986), edited by K.A Jeffs (chapter 9), herein incorporated by reference in its entirety.

The term "seed treatment" comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting. Preferred application methods are: (A) Seed treatment, wherein the seed is treated with the mixture composition prior to planting the seed; (B) Preemergence or postemergence application.

i. Preemergence refers to application of the mixture composition before the plants has emerged from the soil. ii. Postemergence refers to application of the mixture composition after the plant has emerged from the soil. For example the mixture composition is sprayed directly at the stem base, leaves, or soil interface of the plants; (C) In-furrow application.

i. T-band application wherein the mixture composition is added before the furrow is closed, but after the plant propagation material is added to the opened furrow; or after the furrow has been closed. ii. Modified in-furrow application wherein a plant propagation material is placed in an open furrow and the mixture composition is added such that it surrounds the plant propagation material, but minimizes the contact with the plant propagation material; iii. granular application, either on fertilizer or a solid carrier applied in-furrow or potentially on side of furrow; (D) Band spray application, wherein the mixture composition is sprayed onto the soil before

i. planting the plant propagation material; or

ii. planting the plant propagation material, and also incorporated the mixture composition into the soil; (E) Irrigation either by

i. drip

ii. trickle on demand systems; or iii. higher volume chemigation systems; (F) At transplanting by

i. dipping, wherein transplants is dipped into the mixture composition prior to transplanting

ii. Drenching, wherein transplants are drenched with a mixture composition after transplanting;

The present invention also comprises seeds coated with or containing the active compound(s). The term "coated with and/or containing" generally signifies that the active ingredient(s) are for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient(s). Suitable seeds are seeds of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugar beet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.

In addition, the mixtures according to the invention may also be used for the treatment of seeds from plants, which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods.

For example, the active mixtures can be employed in treatment of seeds from plants, which are resistant to herbicides from the group consisting of the sulfonylureas, imidazolinones, glufosinate-ammonium or glyphosate- isopropylammonium and analogous active substances (see for example, EP-A- 0242236, EP-A-0242246) (WO 92/00377) (EP-A-0257993, U.S. Pat. No. 5,013,659) or in transgenic crop plants, for example cotton, with the capability of producing Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A-0 142924, EP-A-0 193259).

Furthermore, the mixtures according to the present invention can be used also for the treatment of seeds from plants, which have modified characteristics in comparison with existing plants consist, which can be generated for example by traditional breeding methods and/or the generation of mutants, or by recombinant procedures). For example, a number of cases have been described of recombinant modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/1 1376, WO 92/14827, WO 91/19806) or of transgenic crop plants having a modified fatty acid composition (WO 91/13972).

The seed treatment application of the mixtures is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.

In the treatment of seeds the corresponding formulations are applied by treating the seeds with an effective amount of the mixture according to the present invention. Herein, but depending on the desired effect, the specific mixture partner(s), pest to be controlled, seed material to be protected and/or weather condition, the application rates of the active compound(s) are generally from 0.01 g to 10 kg per 100 kg of seed, preferably from 0.1 g to 5 kg per 100 kg of seed, in particular from 0.1 g to 2.5 kg per 100 kg of seed.

Compositions, which are especially useful for seed treatment are e.g.: A) Soluble concentrates (SL, LS), D) Emulsions (EW, EO, ES), E) Suspensions (SC, OD, FS), F) Water-dispersible granules and water-soluble granules (WG, SG) G) Water-dispersible powders and water-soluble powders (WP, SP, WS), H) Gel-Formulations (GF), I) Dustable powders (DP, DS).

Conventional seed treatment formulations include for example flowable concentrates FS, suspension concentrates SC, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pre- germinated the latter. In a preferred embodiment a SC or FS formulation is used for seed treatment. Typcially, a SC or FS concentrated formulation, e.g. for seed treatment use, may comprise 1-800 g/1 of active ingredients, 1-200 g/1 Surfactant, 0-200 g/1 antifreezing agent, 0- 400 g/1 of binder, 0-200 g/1 of a pigment and up to 1 liter of a solvent, preferably water.

Preferred FS formulations of mixtures disclosed herein for seed treatment usually comprise from 0.1 to 80% by weight ( 1 to 800 g/1) of the active ingredient(s), from 0.1 to 20 % by weight ( 1 to 200 g/1) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g. 1 to 40 % by weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0 .1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a , antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.

Seed treatment formulations may additionally also comprise binders and optionally colorants.

Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are block copolymers EO/PO surfactants but also polyvinylalcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, polyethyle-neimines, polyethers, polyurethans, polyvinylacetate, tylose and copolymers derived from these polymers.

Optionally, also colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48: 1, pigment red 57: 1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

Biological efficacy The weight ratio of compound (I) to compound(s) (II) is selected to provide a synergistic pesticidal action, i.e. the compound(s) (I) be is present in an activity enhancing amount with respect to compound(s) (II) or vica versa.

A synergistic effect exists whenever the action of a combination of two chemicals is greater than the sum of the action of each of the chemicals alone. Therefore, a synergistic combination is a combination of chemical components having an action that is greater than the sum of the action of each chemical component alone, and a synergistically effective amount is an effective amount of a synergistic combination. Synergism can involve either 2 pesticides, or one pesticide plus a substance that is not by itself toxic to the pest, and such a substance is termed a synergist, i.e. a chemical that enhances the toxicity of a pesticide to a pest.

Well-known methods for determining whether synergy exists include the Colby method, the Tammes method and the Wadley method, all of which are described below. Any one of these methods may be used to determine if synergy exists between the compounds (I) and (II). In the Colby method, also referred to as the Limpels method, the action to be expected E for a given active ingredient combination obeys the so-called Colby formula. According to Colby, the expected action of ingredients (I)+(II) using p+q ppm of active ingredient is:

100 where ppm=milligrams of active ingredient (=a.i.) per liter of spray mixture X=% action by compound (I) using p ppm of active ingredient Y=% action by compound (II) using q ppm of active ingredient. If the ratio R defined as the action actually observed (O) divided by the expected action (E) is > 1 then the action of the combination is superadditive, i.e. there is a synergistic effect. For a more detailed description of the Colby formula, see Colby, S. R . "Calculating synergistic and antagonistic responses of combination," Weeds, Vol. 15, pages 20-22; 1967; see also Limpel et al., Proc. EWCC 16: 48-53 (1962).

The Tammes method uses a graphic representation to determine whether a synergistic effect exists. See "Isoboles, a graphic representation of synergism in pesticides," Netherlands Journal of Plant Pathology, 70 (1964) p . 73-80.

The Wadley method is based on comparison of an observed ED 0 value (i.e. dose of a given compound or combination of compounds providing 50% pest control) obtained from experimental data using the dose response curves and an expected ED 0 calculated theoretically from the formula:

a + b ED50 ((I) + (II))exp =

ED50 (I)obs ED50 (II)obs wherein a and b are the weight ratios of compound (I) and (II) in the mixture

bs and ED 0 o is the experimentally determined ED 0 value obtained using the dose response curves for the individual compounds. The ratio

ED5o ((I)+(II))expected ED o((I)+(II ))observed expresses the factor of interaction (F) (synergy factor). In case of synergism, F is >1. The same formula applies when

LD 0 values are used, i.e. lethal dose, as well as EC50 values, i.e. effective concentration, and LC50 values, i.e. lethal concentration. For a more detailed description of the Wadley method, see Levi et al, EPPO-Bulletin 16, 1986, 651- 657.

An alternative approach as mentioned by D.L. Richer (Pesticide Science, 1987, 19, 309-315, especially p . 313) to determine synergy is based on purely observed values rather than observed and theoretical calculated values as used in the previously mentioned methods. In this alternative method the effect of a given rate of the mixture A and B is compared with the effect of the same rate of each of (I) and (II) used alone. If synergism exists, the observed effect of the mixture will be greater than the observed effect of either component used alone:

E s (x(I)+y(H))>E s (x + y)(I), and > E s (x + y )(II) wherein x and y are the quantities of (I) and (II) in the mixture.

Examples

Comparative example 1 The compound (I) was tested in comparison with in comparison with its (IS, cis)-enantiomer, i.e the compound 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(\S)- cis-3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethylcyclopropane- carboxylate (compound (1,5))

Appropriate doses of the compounds were applied to the insects, Dysdercus cingulatus (Cotton Stainer) by topical application in a non-randomized petridish trial. Visual evaluation of efficacy (percent mortality) at 24 hours after treatment (HAT) was recorded. The compounds were applied as acetone formulations. As control test a blank acetone formulation was also applied to ensure non-effect from the solvent. Table 3: Comparative test for compound (I) and compound ( ,S

1. Activity against Southern armyworm (Spodoptera eridania), 2nd instar larvae The active compounds are formulated for testing the activity against insects and arachnids as a 10.000 ppm solution in a mixture of 35% acetone and water, which is diluted with water, if needed.

A Sieva lima bean leaf is dipped in the test solution and allowed to dry. The leaf is then placed in a petri dish containing a filter paper on the bottom and ten 2nd instar caterpillars. At 5 days, observations are made of mortality and reduced feeding.

2. Activity against diamond back moth (plutella xylostella) The active compounds are formulated in 50:50 acetone:water and 0.1 % (vol/vol) Alkamuls EL 620 surfactant. A 6 cm leaf disk of cabbage leaves is dipped in the test solution for 3 seconds and allowed to air dry in a Petri plate lined with moist filter paper. The leaf disk is inoculated with 10 third instar larvae and kept at 25-27 and 50-60% humidity for 3 days. Mortality is assessed after 72 h of treatment.

3. Activity against cowpea aphid (aphis craccivora) The active compounds were formulated in 50:50 acetone:water. Potted cowpea plants colonized with 100 - 150 aphids of various stages were sprayed after the pest population has been recorded. Population reduction was recorded after 24, 72, and 120 hours.

4. Activity against Vetch aphid (Megoura viciae) The active compounds are formulated in 1:3 DMSO:water. Bean leaf disks are placed into microtiterplates filled with 0.8% agar-agar. The leaf disks are sprayed with 2.5 µΐ of the test solution and 5 to 8 adult aphids are placed into the microtiterplates which are then closed and kept at a temperature of 22-24°C and 35-45% relative humidity under fluorescent light for 6 days. Mortality is assessed on the basis of vital, reproduced aphids. Tests are replicated 2 times.

5. Activity against Wheat aphid (Rhopalosiphumpadi) The active compounds are formulated in 1:3 DMSO:water. Barley leaf disks are placed into microtiterplates filled with 0.8% agar-agar. The leaf disks are sprayed with 2.5 µΐ of the test solution and 3 to 8 adult aphids are placed into the microtiterplates which are then closed and kept at a temperature of 22-24°C and 35-45% relative humidity under fluorescent light for 5 days. Mortality is assessed on the basis of vital aphids. Tests are replicated 2 times.

6. Activity against Cotton aphid (Aphis gossypii) The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic surfactant.

Cotton plants at the cotyledon stage (one plant per pot) were infested by placing a heavily infested leaf from the main colony on top of each cotyledon. The aphids were allowed to transfer to the host plant overnight, and the leaf used to transfer the aphids was removed. The cotyledons were dipped in the test solution and allowed to dry. After 5 days, mortality counts were made.

7. Activity against silverleaf whitefly (bemisia argentifolii) The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic surfactant.

Selected cotton plants were grown to the cotyledon state (one plant per pot). The cotyledons were dipped into the test solution to provide complete coverage of the foliage and placed in a well-vented area to dry. Each pot with treated seedling was placed in a plastic cup and 10 to 12 whitefly adults (approximately 3-5 day old) were introduced. The insects were collected using an aspirator and an 0.6 cm, non-toxic Tygon tubing (R-3603) connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. The cups were covered with a re-usable screened lid (150 micron mesh polyester screen PeCap from Tetko Inc). Test plants were maintained in the holding room at about 25°C and 20-40% relative humidity for 3 days avoiding direct exposure to the fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment of the plants.

8. Green Peach Aphid Myz s persicae) The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic surfactant.

Pepper plants in the 2nd leaf-pair stage (variety 'California Wonder') were infested with approximately 40 laboratory-reared aphids by placing infested leaf sections on top of the test plants. The leaf sections were removed after 24 hr. The leaves of the intact plants were dipped into gradient solutions of the test compound and allowed to dry. Test plants were maintained under fluorescent light (24 hour photoperiod) at about 250°C and 20-40% relative humidity. Aphid mortality on the treated plants, relative to mortality on check plants, was determined after 5 days. 9. Activity against Musca (Musca domestica) The active compounds were formulated in acetone. The topical application comprised application of a single 2-µ1drop to the dorsal thorax using an Arnold Hand-Operated Applicator (Burkard Manufacturing Co., Herts, England). Treated insects are transferred to observation chambers. The dose-mortality relationship for each compound is assessed after 4, 24 and 48 hours (5 insects treated per dose) from four doses or with acetone alone (control).

10. Synergistic effect between the compound (I) and gamma-cyhalothrin.

Appropriate doses of the active ingredients were applied to the insects, Dysdercus cingulatus (cotton stainer), both as single applications as well as mixtures thereof by topical application in a non-randomized petridish trial. Following visual evaluation of efficacy (percent mortality) at selected hours after treatment (HAT), synergy was determined using Colby's formula. Assessment= NUMINS (number of dead insects). The actives were applied as acetone formulations. As control test a blank acetone formulation was also applied to ensure non-effect from the solvent.

As comparative test, similar applications were made using a double dose of tefluthrin (TEF) compared to the amount of the compound (I).

Results provided in table 4 .

Table 4 : Result of test for a combination of compound (I) and gamma- cyhalothrin (GCH).

24HAT Rate Observed Expected R (ng/insect) effect effect Compound (I) 0.8 4 Tefluthrin 1.6 0 GCH 0.625 38 Compound (I) 0.8 + 0.625 64 40.48 1.58 +GCH

TEF +GCH 1.6 + 0.225 38 38 1.0

11. Synergistic effect between the compound (I) and abamectin.

Same procedure as in example 10, with results as provided in table 5.

Table 5 : Result of test for a combination of compound (I) and abamectin (ABA)

24HAT

12. Synergistic effect between the compound (I) and chlorpyrifos.

Same procedure as in example 10, with results as provided in table 6 . Table 6 : Result of test for a combination of compound (I) and chlorpyrifos (CPF)

24HAT

13. Synergistic effect between the compound (I) and fipronil.

Same procedure as in example 10, with results as provided in table 7 .

Table 7 : Result of test for a combination of compound (I) and fipronil (FIP).

24HAT P A T E N T C L A I M S

1. A mixture of the compound (I) which is 2,3,5,6-tetrafluoro-4-methylbenzyl

(Z)-( 1R)-cw-3-(2-chloro-3,3,3-trifluoro- 1-propenyl)-2,2- dimethylcyclopropanecarboxylate and one or more of compound(s) (II) which is an insecticide, acaricide, nematicide and/or fungicide.

2 . A mixture according to claim 1, wherein the compound (I) is substantially free of any other isomer of 2,3,5,6-tetrafluoro-4-methylbenzyl 3-(2-chloro- 3,3,3-trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate.

3 . A mixture according to claim 1 and 2 having insecticidal, nematicidal or acaricidal activity.

4 . A mixture according to any of claims 1 to 3 wherein the compound(s) (II) is an insecticide, acaricide and/or nematicide selected among Acetylcholinesterase (AChE) inhibitors, GABA-gated chloride channel antagonists, Sodium channel modulators/voltage-dependent sodium channel blockers, Nicotinergic acetylcholine receptor agonists, Allosteric acetylcholine receptor modulators, Chloride channel activators, Juvenile hormone mimics, gassing agents, Selective homopteran feeding blockers, Mite growth inhibitors, Microbial disruptors of insect midgut membranes, Inhibitors of mitochondrial ATP synthase, Uncouplers of oxidative phosphorylation. Nicotinic acetylcholine receptor channel blockers,

Inhibitors of chitin biosynthesis type 0 and 1, Moulting disruptors, Ecdysone receptor agonists/disruptors, Octopamine receptor agonists, Mitochondrial complex III electron transport inhibitors, Mitochondrial complex I electron transport inhibitors, Voltage-dependent sodium channel blockers, Inhibitors of acetyl CoA carboxylase, Mitochondrial complex IV electron inhibitors, Mitochondrial complex II electron transport inhibitors, and Ryanodine receptor modulators. 5. A mixture according to claim 4 wherein compound(s) (II) is selected among Organophosphates, Phenylpyrazoles, Pyrethroids, Chloronicotinyls, Avermectins, Spinosyns, and Diamides.

6 . A mixture according to claim 5 wherein the compound(s) (II) is selected among chlorpyrifos, chlorpyrifos-methyl, fipronil, deltamethrin, lambda- cyhalothrin, gamma-cyhalothrin, bifenthrin, acetamiprid, imidacloprid, thiacloprid, thiamethoxam, abamectin, spinosad, spinetoram, chlorantraniliprole, cyanantraniliprole and flubendiamide.

7 . A mixture according to any of claims 1 to 2 wherein the compound(s) (II) is selected among fungicides.

8. A mixture according to claim 7 wherein the compound(s) (II) is selected among methyl benzimidazole carbamate (MBC) fungicides; dicarboximide fungicides; demethylation inhibitor (DMI) fungicides; phenylamide fungicides; amine/morpholine fungicides; phospholipid biosynthesis inhibitor fungicides; carboxamide fungicides; hydroxy(2-amino-)pyrimidine fungicides; anilinopyrimidine fungicides; N-phenyl carbamate fungicides; quinone outside inhibitor (Qol) fungicides; phenylpyrrole fungicides; quinoline fungicides; lipid peroxidation inhibitor fungicides; melanin biosynthesis inhibitors-reductase (MBI-R) fungicides; melanin biosynthesis inhibitors-dehydratase (MBI-D) fungicides; hydroxyanilide fungicides; squalene-epoxidase inhibitor fungicides; polyoxin fungicides; phenylurea fungicides; quinone inside inhibitor (Qil) fungicides; benzamide fungicides; enopyranuronic acid antibiotic fungicides; hexopyranosyl antibiotic fungicides; glucopyranosyl antibiotic: protein synthesis fungicides; glucopyranosyl antibiotic: trehalase and inositol biosynthesis fungicides; cyanoacetamideoxime fungicides; carbamate fungicides; oxidative phosphorylation uncoupling fungicides; organo tin fungicides; carboxylic acid fungicides; heteroaromatic fungicides; phosphonate fungicides; phthalamic acid fungicides; benzotriazine fungicides; benzene-sulfonamide fungicides; pyridazinone fungicides; hiophene-carboxamide fungicides; pyrimidinamide fungicides; carboxylic acid amide (CAA) fungicides; tetracycline antibiotic fungicides; thiocarbamate fungicides; benzamide fungicides; host plant defense induction fungicides; and multi-site contact activity fungicides.

9 . A method for controlling harmful pests comprising the exposure of said harmful pests to an effective amount of the mixture according to claim 1.

10. A method according claim 9 comprising the exposure of the harmful pests, their food supply, habitat, breeding grounds or their loci to an effective amount of the mixture according to claim 1.

11. A method for protecting crops from attack or infestation by harmful pests comprising the exposure of the plant, or the soil, or water in which the plant

is growing with an effective amount of the mixture according to claim 1.

12. A method according to claim 11 wherein the exposure is to the plant, plant propagation material, part of the plant and/or plant organ that grow at a later point in time.

13. The method according to claim 11, comprising the employment of 2 to 2000 g/ha of the mixture according to claim 1.

14. A composition comprising an effective amount of the mixture according to claim 1 in a weight ratio of compound(I):compound(II) ranging from about 1000:1 to about 1:1000.

15. A composition according to claim 14 in a form selected among ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders, granules, soluble granules, dispersible granules, microemulsions, microcapsule suspensions and mixtures thereof. 16. A process for preparing a composition according to any of the claims 14 to 15, which comprise mixing compound (I) and one or more compounds (II) with a diluent(s) and/or surfactant(s).

17. Use of the mixture according to claim 1 for controlling harmful pests.

18. Use according to claim 17 comprising the exposure of the harmful pests to an effective amount of the mixture according to claim 1.

19. Use according claim 18 wherein the exposure is to the harmful pests, their food supply, habitat, breeding grounds or their loci.

20. Use according to claim 18 or 19 wherein the harmful pests are exposed to a composition according to claim 14.

21. Use of the mixture according to claim 1 for protecting crops from attack or infestation by harmful pests comprising the exposure of the plant, plant propagation material, part of the plant and/or plant organ that grow at a later point in time, by applying an effective amount of the mixture on the plant, part of the plant, plant organ, plant propagation material or a surrounding area thereof.

22. Use according to claim 21, comprising the employment of 2 to 2000 g/ha of the mixture according to claim 1. International application No PCT/DK2014/050264

A. CLASSIFICATION O F SUBJECT MATTER INV. AO1N53/00 A01N43/9O A01N57/16 AO1N47/02 A01P7/OO ADD.

According to International Patent Classification (IPC) or to both national classification and IPC

B. FIELDS SEARCHED Minimum documentation searched (classification system followed by classification symbols) A01N

Documentation searched other than minimum documentation to the extent that such documents are included in the fields searched

Electronic data base consulted during the international search (name of data base and, where practicable, search terms used)

EPO-Internal , WPI Data, CHEM ABS Data

C. DOCUMENTS CONSIDERED TO BE RELEVANT

Category* Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No.

WO 02/06202 Al (SYNGENTA LTD [GB] ; BROWN 1-7, STEPHEN MARTIN [GB] ; GOTT BRIAN DAVID 9-12, [GB] ) 24 January 2002 (2002-01-24) 15-21 page 2 , 1i ne 8 - 1ine 9 1-22 page 17, l ine 1 - page 18, l i ne 11 c l aims 11-13

Laszl o Pap: " Pyrethroi ds" 1-22 In: " Encyclopedia of Agrochemi cal s " , 15 Apri l 2003 (2003-04-15) John Wi ley & Sons , http : //on 1inel ibrary.wi ley.com/doi /10. 1002 /047126363X.agr207/ful l , XP055145502 , pages 1-84, D0I : 10. 1002/047126363X.agr207 , page 27; tabl e 5

/ -

X Further documents are listed in the continuation of Box C. See patent family annex.

* Special categories of cited documents : "T" later document published after the international filing date or priority date and not in conflict with the application but cited to understand "A" document defining the general state of the art which is not considered the principle or theory underlying the invention to be of particular relevance "E" earlier application or patent but published on or after the international "X" document of particular relevance; the claimed invention cannot be filing date considered novel or cannot be considered to involve an inventive "L" document which may throw doubts on priority claim(s) orwhich is step when the document is taken alone cited to establish the publication date of another citation or other " document of particular relevance; the claimed invention cannot be special reason (as specified) considered to involve an inventive step when the document is "O" document referring to a n oral disclosure, use, exhibition or other combined with one or more other such documents, such combination means being obvious to a person skilled in the art "P" document published prior to the international filing date but later than the priority date claimed "&" document member of the same patent family

Date of the actual completion of the international search Date of mailing of the international search report

10 October 2014 22/10/2014

Name and mailing address of the ISA/ Authorized officer European Patent Office, P.B. 5818 Patentlaan 2 NL - 2280 HV Rijswijk Tel. (+31-70) 340-2040, Fax: (+31-70) 340-3016 Habermann, Jorg International application No PCT/DK2014/050264

C(Continuation). DOCUMENTS CONSIDERED TO BE RELEVANT

Category* Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No.

DATABASE WPI 1 ,3-6, Week 201030 9-22 Thomson Scienti f i c , London, GB; A N 2010-D58681 XP002730896, & CN 1 1 669 505 A (SHENZHEN N0P0SI0N CO LTD) 17 March 2010 (2010-03-17) Y abstract 1-22

X DATABASE WPI 1 ,3-6, Week 201062 9-22 Thomson Scienti f i c , London, GB; A N 2010-J99965 XP002730897, & CN 101 755 829 A (UNIV YANGZH0U) 3 June 2010 (2010-06-30) abstract

W0 02/30201 A2 (MONSANTO TECHNOLOGY LLC 1 ,3-6, [US] ; ASRAR JAWED [US] ; K0HN FRANK C [US] ) 9-22 18 Apri l 2002 (2002-04-18) Y exampl e 2 1-22

X DE 10 2004 040719 Al (BAYER CROPSCI ENCE AG 1 ,3-6, [DE] ) 2 March 2006 (2006-03-02) 9-22 Y exampl es 1, 2 1-22 c l aims 1 , 2

X DE 10 2006 010205 Al (BAYER CROPSCI ENCE AG 1 ,3-6, [DE] ) 13 September 2007 (2007-09-13) 9-22 Y paragraph [0009] 1-22 page 9 ; table 1

X EP 2 382 865 Al (BAYER CROPSCI ENCE AG 1 ,3,4, [DE] ) 2 November 2011 (2011-11-02) 9-22 Y tables A-l 1-22

Y JOHN C. WICKHAM: " Independent and joi nt 1-22 b i ologi cal activi t y of i someri c forms of syntheti c pyrethroids" , PESTICIDE SCI ENCE, vol . 7 , no. 3 , 1 June 1976 (1976-06-01) , pages 273-277 , XP055145678, ISSN : 0031-613X, D0I : 10. 1002/ps. 2780070311 the whole document

-/-- International application No PCT/DK2014/050264

C(Continuation). DOCUMENTS CONSIDERED TO BE RELEVANT

Category* Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No.

Y MICHAEL ELLIOTT ET AL: 1 Insecti c i dal 1-22 Activi t y of the and Rel ated Compounds . Part XI . Relati ve Potencies of I someri c Cyano-substi tuted 3-Phenoxybenzyl Esters" , PESTICIDE SCI ENCE, ELSEVI ER APPLI ED SCI ENCE PUBLISHER. BARKING, GB, vol . 9 , no. 2 , 1 Apri l 1978 (1978-04-01) , pages 112-116, XP001464878, ISSN : 0031-613X the whole document

X EP 0 370 905 Al (ROUSSEL UCLAF [FR] ) 1 ,3,7-22 30 May 1990 (1990-05-30) Y page 4 , 1i ne 7 - 1ine 12 1-22 page 4 , 1i ne 18 - 1ine 27 International application No Information on patent family members PCT/DK2014/050264

Patent document Publication Patent family Publication cited in search report date member(s) date

WO 0206202 Al 24-01-2002 AT 483677 T 15-10 2010 AU 7082901 A 30-01 2002 B R 0112528 A 01-07 2003 CA 2413472 Al 24-01 2002 CN 1443153 A 17-09 2003 EP 1303474 Al 23-04 2003 ES 2352883 T3 23-02 2011 HU 0301001 A2 28-08 2003 J P 5047441 B2 10-10 2012 J P 2004504290 A 12-02 2004 KR 20030017639 A 03-03 2003 US 2003199709 Al 23- 10 2003 W0 0206202 Al 24- 0 1 2002

CN 101669505 A 17·-03- 2010 NONE

CN 101755829 A 30·-06- 2010 NONE

WO 0230201 A2 18·-04- 2002 A R 030985 Al 03-09-2003 AT 362704 T 15-06-2007 AU 1133502 A 22-04-2002 B R 0114446 A 03-02-2004 CA 2423995 Al 18-04-2002 CN 1479575 A 03-03-2004 CY 1108057 Tl 12-02-2014 DE 60128577 T2 20-09-2007 DK 1322165 T3 01-10-2007 EP 1322165 A2 02-07-2003 ES 2287165 T3 16-12-2007 MX PA03003071 A 14-07-2003 PT 1322165 E 22-08-2007 US 2002129406 Al 12-09-2002 US 2005148470 Al 07-07-2005 W0 0230201 A2 18-04-2002

DE 102004040719 Al 02-03-2006 DE 102004040719 Al 02-03-2006 W0 2006021323 Al 02-03-2006

DE 102006010205 Al 13-09-2007 A R 059755 Al 30-04-2008 DE 102006010205 Al 13-09-2007 T W 200800861 A 01-01-2008 W0 2007101539 A2 13-09-2007

EP 2382865 Al 02 -11- 2011 EP 2382865 Al 02-11-2011 T W 201204258 A 01-02-2012 US 2011275583 Al 10-11-2011 WO 2011134964 Al 03-11-2011

EP 0370905 Al 3 -05- 1990 CA 2003586 Al 23-05-1990 EP 0370905 Al 30-05-1990 FR 2639186 Al 25-05-1990 HU 205840 B 28-07-1992 P H02200604 A 08-08-1990