US009089135B2

(12) United States Patent (10) Patent No.: US 9,089,135 B2 Andersch et al. (45) Date of Patent: Jul. 28, 2015

(54) NEMATICIDAL, INSECTICIDAL AND 2003/0176428 A1 9/2003 Schneidersmann et al. ACARCIDAL ACTIVE INGREDIENT 2006/01 11403 A1 5/2006 Hughes et al. 2007/02O3191, A1* 8/2007 Loso et al...... 514,336 COMBINATIONS COMPRISING 2009, O247551 A1 10/2009 Jeschke et al. PYRIDYL-ETHYLBENZAMIDES AND 2009,0253749 A1 10/2009 Jeschke et al. INSECTICDES 2010/024O705 A1 9/2010 Jeschke et al. 2011 0110906 A1 5/2011 Andersch et al. (75) Inventors: Wolfram Andersch, Bergisch Gladbach 2014,0005047 A1 1/2014 Hungenberg elal. (DE); Heike Hungenberg, Langenfeld FOREIGN PATENT DOCUMENTS (DE); Heiko Rieck, Burscheid (DE) EP O 146748 B1 5, 1988 (73) Assignee: Bayer Intellectual Property GmbH, EP O 16O 344 B1 6, 1988 EP O538588 A1 4f1993 Monheim (DE) EP O 580374, A1 1, 1994 WO WO 83,0087.0 A1 3, 1983 (*) Notice: Subject to any disclaimer, the term of this WO WO 97.22593 A1 6, 1997 patent is extended or adjusted under 35 WO WO 02/28.186 A2 4/2002 U.S.C. 154(b) by 361 days. WO WO O2/080675 A1 10, 2002 WO WOO3,O15519 A1 2, 2003 WO WO 2004/O16088 A2 2, 2004 (21) Appl. No.: 12/731,812 WO WO 2005, O77901 A1 8, 2005 WO WO 2007 115646 A1 10/2007 (22) Filed: Mar. 25, 2010 WO WO 2007 115644 A1 * 10, 2007 WO WO 2007/149134 A1 12/2007 (65) Prior Publication Data WO WO 2008/OO3738 A1 1, 2008 WO WO 20091472O5 A2 * 12/2009 US 2010/O249.193 A1 Sep. 30, 2010 OTHER PUBLICATIONS (30) Foreign Application Priority Data Bauer, T.A., et al., “Response of Selected Weed Species to Postemergence Imazethapyr and Bentazon.” Weed Tech. 9:236-242, Mar. 25, 2009 (EP) ...... 0.9156175 The Weed Science Society of America, United States (1995). Blackshaw, R.E., "HOE-39866 Use in Chemical Fallow Systems.” (51) Int. Cl. Weed Tech. 3:420-428. The Weed Science Society of America, United AOIN 25/00 (2006.01) States (1989). AOIN 43/40 (2006.01) Blackshaw, R.E., "Synergistic Mixes of DPX-A7881 and Clopyralid (52) U.S. Cl. in Canola (Brassica napus).' Weed Tech. 3:690-695. The Weed Sci CPC ...... A0IN 43/40 (2013.01) ence Society of America, United States (1989). (58) Field of Classification Search Blackshaw, R.E., et al., “Herbicide Combinations for Postemergent CPC ...... CO5G 3/02 Weed Control in Safflower (Carthamus tinctorius).' Weed Tech. 4: 97 104. The Weed Science Society of America, United States (1990). USPC ...... 424/405 Blouin, D.C., et al., “Analysis of Synergistic and Antagonistic Effects See application file for complete search history. of Herbicides Using Nonlinear Mixed-Model Methodology.” Weed Tech. 18:464–472. The Weed Science Society of America, United (56) References Cited States (2004). Bradley, P.R., et al., “Response of Sorghum (Sorghum bicolor) to U.S. PATENT DOCUMENTS Atrazine, Ammonium Sulfate, and Glyphosate.” Weed Tech. 14:15 2,596,076 A 5, 1952 Hook et al. 18. The Weed Science Society of America, United States (2000). 2.978.479 A 4, 1961 Kayser et al. Buker, III, R.S., et al., “Confirmation and Control of a Paraquat 3,112,244. A 1 1/1963 Goyette et al. Tolerant Goosegrass (Eleusine indica) Biotype.” Weed Tech. 16:309 3,217,037 A 1 1/1965 Payne, Jr. et al. 313. The Weed Science Society of America, United States (2002). 3.244,586 A 4/1966 Rigterink Burke, I.C., et al., “CGA-362622 Antagonizes Annual Grass Control 3,313,684. A 4/1967 Schegk et al. with Clethodim.” Weed Tech. 16:749-754, The Weed Science Society 3,470,299 A 9, 1969 Heiss et al. of America, United States (2002). 3,530,220 A 9, 1970 Buchanan et al. 3,867,396 A 2f1975 Dawes et al. (Continued) 3,962,316 A 6, 1976 Kiehset al. 4,004,031 A 1/1977 Drabek et al. Primary Examiner — Benjamin Packard 4,006,231 A 2f1977 Black et al. 4,245,432 A 1/1981 Dannelly et al. (74) Attorney, Agent, or Firm — Sterne, Kessler, Goldstein 4,272.417 A 6, 1981 Barke et al. & FOX PLLC 4,310,519 A 1/1982 Albers-Schonberg et al. 4,474,775 A 10, 1984 Okada et al. (57) ABSTRACT 4,782,174 A 11, 1988 Fuchs et al. 4,808.430 A 2f1989 Kouno The present invention relates to novel active ingredient com 4,889,872 A 12, 1989 Naumann et al. binations which consist of fluopyram and further known 5,876.739 A 3, 1999 Turnbladet al. active insecticidal ingredients, and are very Suitable for con 6,114,374. A 9, 2000 Lieb et al. 6.255,342 B1 7/2001 Lieb et al. trolling pests, such as and/or unwanted acarids 6,359,151 B2 3, 2002 Lieb et al. and/or nematodes, in foliar and soil application and/or in seed 7,247,647 B2 7/2007 Hughes et al. treatment. 7,572,818 B2 8, 2009 Mansfield et al. 2002/0010204 A1 1/2002 Lieb et al. 28 Claims, No Drawings US 9,089,135 B2 Page 2

(56) References Cited Palmer, E.W., et al., “Broadleaf Weed Control in Soybean (Glycine max) with CGA-277476 and Four Postemergence Herbicides.” Weed OTHER PUBLICATIONS Tech. 14:617-623. The Weed Science Society of America, United States (2000). Colby, S.R., "Calculating synergistic and antagonistic responses of Rummens, F.H.A., “An Improved Definition of Synergistic and herbicide Combinations.” Weeds 15:20-22, Weed Science Society of Antagonistic Effects.” Weed Science 23(1):4-6, The Weed Science America, United States (1967). Society of America, United States (1975). Flint, J.L., et al., “Analyzing Herbicide Interactions, a Statistical Salzman, F.P., and Renner, K.A., “Response of Soybean to Combi Treatment of Colby's Method.” Weed Tech. 2:304-309. The Weed nations of ClomaZone, Metribuzin, Linuron, Alachlor, and Atrazine.” Science Society of America, United States (1988). Weed Tech. 6:922-929. The Weed Science Society of America, United Gillespie, G.R., and Nalewaja, J.D., “Wheat (Triticum aestivum) States (1992). Scott, R.C., et al., “Spray Adjuvant, Formulation, and Environmental Response to Triallate Plus Chlorsulfuron.” Weed Tech. 3:20-23. The Effects on Synergism from Post-Applied Tank Mixtures of SAN Weed Science Society of America, United States (1989). 582H with Fluazifop-P Imazethapyr, and Sethoxydim.” Weed Tech. Green, J.M., et al., “Metribuzin and Chlorimuron Mixtures for 12:463-469. The Weed Science Society of America, United States Preemergence Broadleaf Weed Control in Soybeans, Glycine may," (1998). Weed Tech. 2:355-363, The Weed Science Society of America, United Shaw, D.R. and Arnold, J.C., "Weed Control from Herbicide Com States (1988). binations with Glyphosate.” Weed Tech. 16:1-6. The Weed Science Harker, N.K., and O'Sullivan, P.A., “Synergistic Mixtures of Society of America, United States (2002). Sethoxydim and Fluazifop on Annual Grass Weeds.” Weed Tech. Snipes, C.E., and Allen, R.L., “Interaction of Graminicides Applied 5:310-316, The Weed Science Society of America, United States in Combination with Pyrithiobac.” Weed Tech. 10:889-892, The (1991). Weed Science Society of America, United States (1996). Kent, L.M., et al., “Effect of Ammonium Sulfate, Imazapyr, and Sun, Y.-P. & Johnson, E.R., “Analysis of Joint Action of Insecticides Environment on the Phytotoxicity of Imazethapyr.” Weed Tech. against House Flies'. J. Econ. Entomol., 53:887-892, Journal of 5:202-205, The Weed Science Society of America, United States Economic Entomology, United States (1960). (1991). Wehtje, G. and Walker, R.H., “Interaction of Glyphosate and 2,4-DB Kotoula-Syka, E., et al., “Interactions between SAN 582H and for the Control of Selected Morningglory (Ipomoea spp.) Species.” Selected Safeners on Grain Sorghum (Sorghum bicolor) and Corn Weed Tech. 11:152-156. The Weed Science Society of America, (Zea mays).” Weed Tech. 10:299-304, The Weed Science Society of United States (1997). America, United States (1996). Zhang, W., et al., “Fenoxaprop Interactions for Barnyardgrass Lanclos, D.Y., et al., "Glufosinate Tank-Mix Combinations in (Echinochloa crus-galli) Control in Rice.” Weed Tech. 19:293-297. Glufosinate-Resistant Rice (Oryza sativa).' Weed Tech. 16:659-663, The Weed Science Society of America, United States (2005). The Weed Science Society of America, United States (2002). English language abstract of European Patent Publication No. EPO Norris, J.L., et al., "Weed Control from Herbicide Combinations with 538588 A1 (1993). Three Formulations of Glyphosate.” Weed Tech. 15:552-558. The Office Action mailed Dec. 8, 2014, in U.S. Appl. No. 13/990,586, Weed Science Society of America, United States (2001). Hungenberg, H., et al., S371 (c) Date: Sep. 18, 2013, U.S. Patent and Novosel, K.M., et al., “Metolachlor Efficacy as Influenced by Three Trademark Office, Alexandria, VA. Acetolactate Synthase-Inhibiting Herbicides.” Weed Tech. 12:248 253, The Weed Science Society of America, United States (1998). * cited by examiner US 9,089,135 B2 1. 2 NEMATICIDAL, INSECTICIDAL AND 2(5H)-one (II-28), 4-(6-chloro-5-fluoropyrid-3-yl)-me ACARCIDAL ACTIVE INGREDIENT thyl(methyl)aminofuran-2(5H)-one (II-29), 4-(5.6- COMBINATIONS COMPRISING dichloropyrid-3-yl)methyl(2-fluoroethyl)aminofuran-2 PYRIDYL-ETHYLBENZAMIDES AND (5H)-one (1'-30), 4-(6-chloro-5-fluoropyrid-3-yl) INSECTICDES methyl (cyclo-propyl)aminofuran-2(5H)-one (II-31), 4 (6-chloropyrid-3-yl)methyl (cyclopropyl)aminofuran The present invention relates to novel active ingredient 2(5H)-one (II-32), 4-(6-chloropyrid-3-yl)methyl combinations which consist of fluopyram and further known (methyl)aminofuran-2(5H)-one (II-33), B-cyfluthrin (II active insecticidal ingredients, and are very Suitable for con 34), transfluthrin (II-35), cyazypyr (II-36), trolling animal pests, such as insects and/or unwanted acarids 10 and/or nematodes, in foliar and soil application and/or in seed chlorantraniliprole (II-37), ethiprole (II-38), sulfoxaflor treatment. (II-39), flonicamid (II-40), methiocarb (II-41), spirotetra It is already known that particular pyridylethylbenzamides mat (II-42) and 5-chloro-2-(3,4,4-trifluorobut-3-en-1-yl) possess fungicidal, insecticidal and acaricidal and nemati sulphonyl-1,3-thiazole (II-43) are very suitable for con cidal properties. 15 trolling phytopathogenic fungi and animal pests, WO 2004/016088 describes pyridylethylbenzamides and especially nematodes, in foliar and Soil application, espe the use thereofas fungicides. The possibility of a combination cially in seed treatment. of one or more of the pyridylethylbenzamide derivatives dis The insecticides or active nematicidal ingredients of group closed with further known fungicides, insecticides, nemati (II) are selected from the group consisting of cides or acaricides for broadening the spectrum of activity is aldicarb (II-1) known from U.S. Pat. No. 3.217,037 likewise described. However, the application teaches neither and/or which insecticidal mixing partners are suitable northe mixing carbofuran (II-2) known from DE-A-1493646 ratio in which insecticides and pyridylethylbenzamide and/or derivatives are combined with one another. WO 2005/077901 oxamyl (II-3) known from DE-A-1768623 teaches fungicidal compositions comprising at least one 25 and/or pyridylethylbenzamide, a fungicide and an inhibitor of elec carbosulfan (II-4) known from DE-A-2433680 tron transport in the respiratory chain of fungi. However, the and/or patent application does not describe any mixtures of pyridyl cloethocarb (II-5) known from DE-A-2231249 ethylbenzamides with insecticides. WO 2008/003738 and/or teaches fungicidal compositions comprising at least one 30 thiodicarb (II-6) known from DE-A-2530439 pyridylethylbenzamide and an insecticide. A possible nem and/or aticidal effect of the compositions is described in the appli fenamiphos (II-7) known from DE-A-1121882 cation, but not explicitly for mixtures comprising N-(2-3- and/or chloro-5-(trifluoromethyl)-2-pyridinylethyl-2- ethoprophos (II-8) known from U.S. Pat. No. 3,112,244 trifluoromethylbenzamide. 35 and/or The efficacy of the active ingredients and active ingredient terbufos (II-9) known from U.S. Pat. No. 2,596,076 compositions described in the prior art is good, but leaves and/or Something to be desired at low application rates in some isazofos (II-10) known from DE-A-2260015 cases, especially in the control of nematodes. and/or It is therefore an object of the present invention to provide 40 pyraclofos (II-11) known from DE-A-3012 193 nematicidal, insecticidal and acaricidal active ingredient and/or combinations with improved efficacy, especially towards cadusafos (II-12) known from WO 83/00870 nematodes. and/or It has now been found that active ingredient combinations chlorethoxyfos (II-13) known from EP-A-160344 comprising 45 and/or (I) N-(2-3-chloro-5-(trifluoromethyl)-2-pyridinylethyl-2- fosthiazate (II-14) known from EP-A-146748 trifluoromethylbenzamide (fluopyram) and/or and the N-oxides thereof chlorpyriphos-methyl (II-15) known from U.S. Pat. No. and 3,244,586 (II) at least one insecticidal or nematicidal active ingredient 50 and/or Selected from the group consisting of aldicarb (II-1), car benzisothiazole (II-16), bofuran (II-2), oxamyl (II-3), carbosulfan (II-4), cloetho and/or carb (II-5), thiodicarb (II-6), fenamiphos (II-7), ethopro abamectin (II-17) known from DE-A-27 17040, phos (II-8), terbufos (II-9), isazofos (II-10), pyraclofos fumigants (II-18), (II-11), cadusafos (II-12), chlorethoxyfos (II-13), fosthiaz 55 Pasteuria penetrans (II-19), ate (II-14), chlorpyriphos-methyl (II-15), benzisothiazole and/or (II-16), abamectin (II-17), fumigants (II-18), Pasteuria Bacillus firmus (II-20), penetrans (II-19), Bacillus firmus (II-20), Bacillus firmus and/or I-1582 (BioNem, Votivo) (II-20a), Metarhizium (II-21), Bacillus firmus I-1582 (BioNem, Votivo) (II-20a), mycorrhiza (II-22), Hirsutella (II-23), 4-(6-bromopyrid 60 and/or 3-yl)methyl(2-fluoroethyl)aminofuran-2(5H)-one (II Metarhizium (II-21), 24), 4-(6-fluoropyrid-3-yl)methyl(2,2-difluoroethyl) and/or aminofuran-2(5H)-one (II-25), 4-(2-chloro-1,3- Mycorrhiza (II-22). Mycorrhiza refer to a class of active thiazol-5-yl)methyl (2-fluoroethyl)aminofuran-2(5H)- ingredients which stimulate the growth of mycorrhizal fungi O (II-26), 4-(6-chloropyrid-3-yl)methyl(2- 65 and as a result improve the active ingredient uptake of plants. fluoroethyl)aminofuran-2(5H)-one (II-27), 4-(6- These include, for example, the strigolactones of the follow chloropyrid-3-yl)methyl(2,2-difluoroethyl)aminofuran ing formulae (II-22a to II-22k):

US 9,089,135 B2 5 6 4-(6-chloro-5-fluoropyrid-3-yl)methyl(methyl) Preference is given to active ingredient combinations com aminofuran-2(5H)-one (II-29) known from WO 2007/ prising the compounds of the formula (I-1) and at least one 115643 A1, active ingredient of the formula (II). and/or The following combinations are of particular interest: 4-(5,6-dichloropyrid-3-yl)methyl-(2-fluoroethyl)amino 5 (I-1)+(II-1), (I-1)+(II-2), (I-1)+(II-3), (I-1)+(II-4), (I-1)+(II furan-2(5H)-one (II-30) known from WO 2007/115646A1, 5), (I-1)+(II-6), (I-1)+(II-7), (I-1)+(II-8), (I-1)+(II-9). (I-1)+ and/or (II-10), (I-1)+(II-11), (I-1)+(I-1)+(II-13), (I-1)+(II-14), 4-(6-chloro-5-fluoropyrid-3-yl)methyl(cyclopropyl) (I-1)+(II-15), (I-1)+(II-16), (I-1)+(II-17), (I-1)+(II-18), aminofuran-2(5H)-one (II-31) known from WO 2007/ (I-1)+(II-19). (I-1)+(II-20), (I-1)+(II-20a), (I-1)+(II-21), 115643 A1, 10 (I-1)+(II-22), (I-1)+(II-23), (I-1)+(II-24), (I-1)+(II-25), and/or (I-1)+(II-26), (I-1)+(II-27). (I-1)+(II-28), (I-1)+(II-29), 4-(6-chloropyrid-3-yl)methyl(cyclopropyl)aminofuran (I-1)+(II-30), (I-1)+(II-31), (I-1)+(II-32), (I-1)+(II-33), 2(5H)-one (II-32) known from EP 0538588 A. (I-1)+(II-34), (I-1)+(II-35), (I-1)+(II-36), (I-1)+(II-37), and/or (I-1)+(II-38), (I-1)+(II-39). (I-1)+(II-40), (I-1)+(II-41), 15 (I-1)+(II-42) and (I-1)+(II-43). 4-(6-chloropyrid-3-yl)methyl(methyl)aminofuran-2 The active ingredient combinations may additionally also (5H)-one (II-33) known from EP 0538588 A, comprise further fungicidally, acaricidally or insecticidally and/or active additive components. |B-cyfluthrin (II-34) known from EP-A-206149, When the active ingredients in the inventive active ingre and/or dient combinations are present in particular weight ratios, the transfluthrin (II-35) known from EP-A-279325, improved action is particularly clearly evident. However, the and/or weight ratios of the active ingredients in the active ingredient cyazypyr (II-36) known from WO 04/067528, combinations can be varied within a relatively wide range. In and/or general, the inventive combinations comprise active ingredi chlorantraniliprole (II-37) known from WO 03/015519, 25 ents of the formula (I-1) and the mixing partner in the pre and/or ferred and particularly preferred mixing ratios specified in the ethiprole (II-38) known from WO97/22593, table below: and/or sulfoxaflor (II-39) known from WO 2007/149134, and/or 30 Mixing Preferred mixing ratio of Particularly preferred mixing flonicamid (II-40) known from EP-A-00580374, artner (I-1):mixing partner ratio of (I-1):mixing partner and/or -1 25:1 to 1:12S 25:1 to 1:25 methiocarb (II-41) known from DE-A 11 62 352, -2 25:1 to 1:12S 25:1 to 1:25 and/or -3 25:1 to 1:12S 25:1 to 1:25 35 -4 25:1 to 1:12S 25:1 to 1:25 spirotetramat (II-42) known from WO98/005638 -S 25:1 to 1:12S 25:1 to 1:25 and/or -6 25:1 to 1:12S 25:1 to 1:25 5-chloro-2-(3,4,4-trifluorobut-3-en-1-yl)sulphonyl-1,3- -7 25:1 to 1:12S 25:1 to 1:25 thiazole (II-43) known from WO 01/02378. -8 25:1 to 1:12S 25:1 to 1:25 -9 25:1 to 1:12S 25:1 to 1:25 In a preferred embodiment of the invention, the insecticidal -10 25:1 to 1:12S 25:1 to 1:25 40 or nematicidal active ingredients of group (II) are selected -11 25:1 to 1:12S 25:1 to 1:25 from the group consisting of benzisothiazole (II-16), fumi -12 25:1 to 1:12S 25:1 to 1:25 gants (II-18), Pasteuria penetrans (II-19), Bacillus firmus -13 25:1 to 1:12S 25:1 to 1:25 -14 2OO:1 to 1:200 SO:1 to 1:SO (II-20), Bacillus firmus I-1582 (BioNem, Votivo) (II-20a), -15 25:1 to 1:12S 25:1 to 1:25 Metarhizium (II-21), Mycorrhiza (II-22), Hirsutella (II-23), -16 25:1 to 1:12S 25:1 to 1:25 4-(6-bromopyrid-3-yl)methyl(2-fluoroethyl) 45 -17 25:1 to 1:12S 25:1 to 1:25 aminofuran-2(5H)-one (II-24), 4-(6-fluoropyrid-3-yl)me -18 25:1 to 1:12S 25:1 to 1:25 thyl(2,2-difluoroethyl)aminofuran-2(5H)-one (II-25), 4 -19 25:1 to 1:12S 25:1 to 1:25 -2O 25:1 to 1:12S 25:1 to 1:25 {(2-chloro-1,3-thiazol-5-yl)methyl(2-fluoroethyl) -20-a 25:1 to 1:12S 25:1 to 1:25 aminofuran-2(5H)-one (II-26), 4-(6-chloropyrid-3-yl) -21 25:1 to 1:12S 25:1 to 1:25 methyl(2-fluoroethyl)aminofuran-2(5H)-one (II-27), 4 50 -22 25:1 to 1:12S 25:1 to 1:25 {(6-chloropyrid-3-yl)methyl(2,2-difluoroethyl) -22 25:1 to 1:12S 25:1 to 1:25 -23 25:1 to 1:12S 25:1 to 1:25 aminofuran-2(5H)-one (II-28), 4-(6-chloro-5-fluoropy -24 25:1 to 1:12S 25:1 to 1:25 rid-3-yl)-methyl(methyl)aminofuran-2(5H)-one (II-29), -2S 25:1 to 1:12S 25:1 to 1:25 4-(5,6-dichloropyrid-3-yl)methyl(2-fluoroethyl) -26 25:1 to 1:12S 25:1 to 1:25 55 -27 25:1 to 1:12S 25:1 to 1:25 aminofuran-2(5H)-one (II-30), 4-(6-chloro-5-fluoropy -28 25:1 to 1:12S 25:1 to 1:25 rid-3-yl)methyl (cyclo-propyl)aminofuran-2(5H)-one (II -29 25:1 to 1:12S 25:1 to 1:25 31), 4-(6-chloropyrid-3-yl)methyl (cyclopropyl) -30 25:1 to 1:12S 25:1 to 1:25 aminofuran-2(5H)-one (II-32), 4-(6-chloropyrid-3-yl) -31 25:1 to 1:12S 25:1 to 1:25 methyl(methyl)aminofuran-2(5H)-one (II-33), -32 25:1 to 1:12S 25:1 to 1:25 -33 25:1 to 1:12S 25:1 to 1:25 chlorantraniliprole (II-37) and sulfoxaflor (II-39). 60 -34 25:1 to 1:12S 25:1 to 1:25 Surprisingly, the fungicidal, insecticidal and/or acaricidal -35 25:1 to 1:12S 25:1 to 1:25 and/or nematicidal action, especially the nematicidal action, -36 25:1 to 1:12S 25:1 to 1:25 of the inventive active ingredient combinations, especially -37 25:1 to 1:12S 25:1 to 1:25 -38 25:1 to 1:12S 25:1 to 1:25 after Soil application, is significantly higher than the Sum of -39 25:1 to 1:12S 25:1 to 1:25 the actions of the individual active ingredients. There is an 65 -40 25:1 to 1:12S 25:1 to 1:25 unforeseeable true synergistic effect, and not just additive -41 25:1 to 1:12S 25:1 to 1:25 actions. US 9,089,135 B2 8 -continued dimethylbutyl)phenyl-5-fluoro-1,3-dimethyl-1H-pyrazole 4-carboxamide, N-(2-1.1'-bi(cyclopropyl)-2-yl)phenyl-3- Mixing Preferred mixing ratio of Particularly preferred mixing (difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, partner (I-1):mixing partner ratio of (I-1):mixing partner 3-(difluoromethyl)-1-methyl-N-(3',4',5'-trifluorobiphenyl II-42 125:1 to 1:12S 25:1 to 1:25 2-yl)-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-N- II-43 125:1 to 1:12S 25:1 to 1:25 4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl-1-me thyl-1H-pyrazole-4-carboxamide, (2E)-2-(2-6-(3-chloro 2-methylphenoxy)-5-fluoropyrimidin-4-yl)oxyphenyl)-2- An alternative embodiment of the present invention relates (methoxyimino)-N-methylethanamide, (2E)-2-2-((2E, to nematicidal active ingredient combinations comprising 10 3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidenelaminooxy) N-2-3-chloro-5-(trifluoromethyl)-2-pyridinylethyl-2- methylphenyl-2-(methoxyimino)-N-methylethanamide, trifluoromethyl-benzamide (I-1) and at least one fungicidal 2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)py active ingredient selected from the group consisting of benal ridine-3-carboxamide, N-(3-ethyl-3,5,5-trimethylcyclo axyl, benalaxyl-M, bupirimate, cloZylacon, dimethirimol, hexyl)-3-(formylamino)-2-hydroxybenzamide, 5-methoxy ethirimol, furalaxyl, hymexaZol, metalaxyl, metalaxyl-M, 15 2-methyl-4-(2-({(1E)-1-3-(trifluoromethyl)phenyl ofurace, oxadixyl and oxolinic acid, benomyl, carbendazim, ethylidene amino)oxymethylphenyl)-2,4-dihydro-3H-1, chlorfenazole, diethofencarb, ethaboxam, fuberidazole, pen 2,4-triazol-3-one, (2E)-2-(methoxyimino)-N-methyl-2-(2- cycuron, thiabendazole, thiophanate, thiophanate-methyl and {({(1E)-1-3-(trifluoromethyl)phenylethylideneamino)- Zoxamide, diflumetorim as inhibitor which acts on complex I oxymethylphenyl)ethanamide, (2E)-2-(methoxyimino)-N- of the respiratory chain; biXafen, boScalid, carboxin, fen methyl-2-2-(E)-(1-3-(trifluoromethyl)phenyl furam, flutolanil, fluopyram, furametpyr, furmecyclox, ethoxy)imino)methylphenylethanamide, (2E)-2-2- isopyrazam (9R component), isopyrazam (9S component), ({(1E)-1-(3-(E)-1-fluoro-2-phenylethenyloxyphenyl) mepronil, oxycarboxin, penthiopyrad, thifluZamid as inhibi ethylidenelamino oxy)methylphenyl)-2-(methoxyimino)- tors which act on complex II of the respiratory chain; amisul N-methylethanamide, 1-(4-chlorophenyl)-2-(1H-1,2,4-tria brom, azoxystrobin, cyaZofamid, dimoxystrobin, enes 25 Zol-1-yl)cycloheptanol, methyl 1-(2,2-dimethyl-2,3- troburin, famoxadone, fenamidone, fluoxastrobin, kresoxim dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate, methyl, metominostrobin, orysastrobin, picoxystrobin, N-ethyl-N-methyl-N'-(2-methyl-5-(trifluoromethyl)-4-3- pyraclostrobin, pyribencarb, trifloxystrobin as inhibitors (trimethylsilyl)propoxyphenyl)imidoformamide, N'-(5- which act on complex III of the respiratory chain, binapacryl, (difluoromethyl)-2-methyl-4-3-(trimethylsilyl)propoxy dinocap, fluaZinam and meptylidinocap, fentin acetate, fentin 30 phenyl-N-ethyl-N-methylimidoformamide, O-1-4- chloride, fentin hydroxide and silthiofam, andoprim, blasti methoxyphenoxy)methyl-2,2-dimethylpropyl)-1H cidin-S, cyprodinil, kasugamycin, kasugamycin hydrochlo imidazole-1-carbothioate, N-2-(4-3-(4-chlorophenyl) ride hydrate, mepanipyrim and pyrimethanil, fenpiclonil, flu prop-2-yn-1-yl)oxy-3-methoxyphenyl)ethyl-N'- dioxonil and quinoxyfen, biphenyl, chloZolinate, edifenphos, (methylsulphonyl) valinamide, 5-chloro-7-(4- etridiazole, iodocarb, iprobenfos, iprodione, isoprothiolane, 35 methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl) 1.2.4 procymidone, propamocarb, propamocarb hydrochloride, triazolo 1.5-alpyrimidine, 5-amino-1,3,4-thiadiazole-2- pyrazophos, tolclofoS-methyl and VincloZolin, aldimorph, thiole, propamocarb-fosetyl, 1-(4-methoxyphenoxy) aZaconazole, bitertanol, bromuconazole, cyproconazole, methyl-2,2-dimethylpropyl 1H-imidazole-1-carboxylate, diclobutrazole, difenoconazole, diniconazole, diniconazole 1-methyl-N-2-(1,1,2,2-tetrafluoroethoxy)phenyl-3-(trif M, dodemorph, dodemorphacetate, epoxiconazole, etacona 40 luoromethyl)-1H-pyrazole-4-carboxamide, 2,3,5,6-tetra Zole, fenarimol, fenbuconazole, fenhexamid, fenpropidin, chloro-4-(methylsulphonyl)pyridine, 2-butoxy-6-iodo-3- fenpropimorph, fluguinconazole, flurprimidol, flusilaZole, propyl-4H-chromen-4-one, 2-phenylphenol and salts flutriafol, furconazole, furconazole-cis, hexaconazole, thereof, 3-(difluoromethyl)-1-methyl-N-2-(1,1,2,2-tet imazalil, imazalil Sulphate, imibenconazole, ipconazole, rafluoroethoxy)phenyl)-1H-pyrazole-4-carboxamide, 3,4,5- metconazole, myclobutanil, naftifine, nuarimol, Oxpocona 45 trichloropyridine-2,6-dicarbonitrile, 3-5-(4-chlorophenyl)- Zole, paclobutraZol, pefurazoate, penconazole, piperalin, 2,3-dimethylisoxazolidin-3-ylpyridine, 3-chloro-5-(4- prochloraz, propiconazole, prothioconazole, pyributicarb, chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, pyrifenox, quinconazole, Simeconazole, Spiroxamine, tebu 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpy conazole, terbinafine, tetraconazole, triadimefon, triadime ridazine, 8-hydroxyquinoline, 8-hydroxyquinoline Sulphate, nol, tridemorph, triflumizole, triforine, triticonazole, uni 50 5-methyl-6-octyl-3,7-dihydro 1,2,4-triazolo 1.5-alpyrimi conazole, Viniconazole and Voriconazole, benthiavalicarb, dine-7-amine, 5-ethyl-6-octyl-3,7-dihydro 1.2.4 triazolo.1, dimethomorph, flumorph, iprovalicarb, mandipropamid, 5-alpyrimidine-7-amine, benthiazol, bethoxazin, capsimy polyoxins, polyoxorim, prothiocarb, validamycin A and cin, carvone, chinomethionat, chloroneb, cufraneb, Valiphenal, carpropamid, diclocymet, fenoxanil, phthalide, cyflufenamide, cymoxanil, cyprosulfamide, dazomet, debac pyroquilon and tricyclazole, acibenzolar-S-methyl, probena 55 arb, dichlorophen, diclomeZine, dicloran, difenZoquat, difen Zole and tiadinil, Bordeaux mixture, captafol, captan, chlo Zoquat methylsulphate, diphenylamin, ecomat, ferimZone, rothalonil, copper naphthenate, copper oxide, copper oxy flumetover, fluopicolide, fluoromide, flusulfamide, flutianil, chloride, copper preparations such as, for example, copper fosetyl-aluminium, fosetyl-calcium, fosetyl-Sodium, hydroxide, copper Sulphate, dichlofluanid, dithianon, dodine hexachlorobenzene, irumamycin, isotianil, methasulfocarb, and its free base, ferbam, fluorofolpet, folpet, guazatline, 60 methyl (2E)-2-2-(cyclopropyl (4-methoxyphenyl)iminol guaZatine acetate, iminoctadine, iminoctadine albesilate, imi methylthio)methylphenyl-3-methoxyacrylate, methyl noctadine triacetate, mancopper, mancoZeb, maneb, meti isothiocyanate, metrafenone, (5-bromo-2-methoxy-4-meth ram, metiram Zinc, oxine-copper, propamidine, propineb, ylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)metha Sulphur and Sulphur preparations such as, for example, cal none, mildiomycin, tolnifanide, N-(4-chlorobenzyl)-3-3- cium polysulphide, thiram, tolylfluanid, Zineb and Ziram, 2.3- 65 methoxy-4-(prop-2-yn-1-yloxy)phenylpropanamide, N-(4- dibutyl-6-chlorothieno 2,3-dipyrimidin-4(3H)-one, ethyl chlorophenyl)(cyano)methyl-3-3-methoxy-4-(prop-2-yn (2Z)-3-amino-2-cyano-3-phenylprop-2-enoate, N-2-(1,3- 1-yloxy)phenylpropanamide, N-(5-bromo-3- US 9,089,135 B2 9 10 chloropyridin-2-yl)methyl-2,4-dichloropyridine-3- Lecanium corni, Saissetia oleae, Laodelphax striatellus, carboxamide, N-1-(5-bromo-3-chloropyridin-2-yl)ethyl-2, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, 4-dichloropyridine-3-carboxamide, N-1-(5-bromo-3- Pseudococcus spp., Psylla spp. chloropyridin-2-yl)ethyl)-2-fluoro-4-iodopyridine-3- From the order of the , for example, Pectino carboxamide, N-(Z)-(cyclopropylmethoxy)imino6 5 phora gossypiella, Bupalus piniarius, Chematobia brumata, (difluoromethoxy)-2,3-difluorophenyl)methyl-2- Lithocolletis blancardella, Hyponomeuta padella, Plutella phenylacetamide, N-(E)-(cyclopropylmethoxy)iminoló xylostella, Malacosoma neustria, Euproctis chrysorrhoea, (difluoromethoxy)-2,3-difluorophenyl)methyl-2- Lymantria spp., Bucculatrix thurberiella, Phyllocnistis cit phenylacetamide, natamycin, nickel rella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, dimethyldithiocarbamate, nitrothal-isopropyl, octhillinone, 10 Heliothis spp., Mamestra brassicae, Panolis flammea, oxamocarb, oxyfenthiin, pentachlorophenol and salts Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, thereof, phenazine-1-carboxylic acid, phenothrin, phospho Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kueh ric acid and salts thereof, propamocarb fosetylate, propa niella, Galleria mellonella, Tineola bisselliella, Tinea pel nosine-sodium, produinazid, pyrrolnitrin, quintoZene, lionella, Hofmannophila pseudospretella, Cacoecia podana, S-prop-2-en-1-yl 5-amino-2-(1-methylethyl)-4-(2-meth 15 Capua reticulana, Choristoneura filmiferana, Clysia ambig ylphenyl)-3-oxo-2,3-dihydro-1H-pyrazole-1-carbothioate, uella, magnanima, Tortrix viridana, Cnaphalocerus tecloftalam, tecnazene, triazoxide, trichlamide, 5-chloro-N'- spp., Oulema oryzae. phenyl-N'-prop-2-yn-1-ylthiophene-2-sulphonohydrazide From the order of the Coleoptera, for example, Anobium and Zarilamide. punctatum, Rhizopertha dominica, Bruchidius Obtectus, Animal Pests Acanthoscelides Obtectus, Hylotrupes bajulus, Agelastica Given good plant compatibility, the active ingredient com alni, Leptinotarsa decemlineata, Phaedon cochleariae, binations are Suitable for controlling animal pests, such as Diabrotica spp., Psylliodes chrysocephala, Epillachna insects and/or arachnids, especially nematodes, which are varivestis, Atomaria spp., Oryzaephilus surinamensis, encountered in Viticulture, fruit growing, in agriculture, in Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, nurseries and in forests. They can preferably be used as crop 25 Cosmopolites Sordidus, Ceuthorrhynchus assimilis, Hypera protection agents. They are effective against normally sensi postica, Dermestes spp., Trogoderma spp., Anthrenus spp., tive and resistant species and against all or particular devel Attagenus spp., Lyctus spp., Melligethes aeneus, Ptinus spp., opment stages. The abovementioned pests include: Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tene Insects brio molitor; Agriotes spp., Conoderus spp., Melolontha From the order of the Isopoda, for example, Oniscus asel 30 melolontha, Amphimallon solstitialis, Costelytra zealandica, lus, Armadillidium vulgare, Porcellio scaber. Lissorhoptrus Oryzophilus. From the order of the Diplopoda, for example, Blaniulus From the order of the Hymenoptera, for example, Diprion guttulatus. spp., Hoplocampa spp., Lasius spp., Monomorium phara From the order of the Chilopoda, for example, Geophilus Onis, Vespa spp. Carpophagus, Scutigera spp. 35 From the order of the Diptera, for example, Aedes spp., From the order of the Symphyla, for example, Scutigerella Anopheles spp., Culex spp., Drosophila melanogaster, Musca immaculata. spp., Fannia spp., Caliphora erythrocephala, Lucilia spp., From the order of the Thysanura, for example, Lepisma Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppo saccharina. bOsca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., From the order of the Collembola, for example, Onychi 40 Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, lirtiS drinatti.S. Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus From the order of the Orthoptera, for example, Acheta Oleae, Tipula paludosa, Hvlemyia spp., Liriomyza spp. domesticus, Gryllotalpa spp., Locusta migratoria migrato From the order of the Siphonaptera, for example, Xenop rioides, Melanoplus spp., Schistocerca gregaria. sylla cheopis, Ceratophyllus spp. From the order of the Blattaria, for example, Blatta orien 45 Arachnids talis, Periplaneta americana, Leucophaea maderae, Blattella From the class of the Arachnida, for example, Scorpio germanica. maurus, Latrodectus mactans, Acarus siro, Argas spp., Orni From the order of the Dermaptera, for example, Forficula thodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyl auricularia. locoptruta oleivora, Boophilus spp., Rhipicephalus spp., From the order of the Isoptera, for example, Reticulitermes 50 Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp. spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., From the order of the Phthiraptera, for example, Pediculus Bryobia praetiosa, Panonychus spp., Tetranychus spp., humanus corporis, Haematopinus spp., Linognathus spp., Hemitarisonemus spp., Brevipalpus spp. Trichodectes spp., Damalinia spp. Nematodes From the order of the Thysanoptera, for example, Herci 55 In principle, all kinds of plant-parasitic nematodes can be nothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella controlled with the inventive active ingredient combinations. occidentalis. The inventive active ingredient combinations are found to be From the order of the Heteroptera, for example, Eurygaster particularly advantageous for controlling nematodes which spp., Dysdercus intermedius, Piesma quadrata, Cimex lectu are selected from the group consisting of Meloidogyne spp., larius, Rhodnius prolixus, Triatoma spp. 60 for example Meloidogyne incognita, Meloidogyne javanica, From the order of the Homoptera, for example, Aleurodes Meloidogyne hapla, Meloidogyne arenaria, Dity lenchus brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis ssp., for example Dity lenchus dipsaci, Ditylellenchus destruc gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis tor, Pratylenchus ssp. for example Pratylenchus penetrans, fabae, Aphis pomi, Eriosoma lanigerum, Hvalopterus arun Pratylenchus fallax, Pratylenchus coffeae, Pratylenchus dinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphun 65 loosi, Pratylenchus vulnus, Globodera spp., for example avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Globodera rostochiensis, Globodera pallida etc.; Heterodera Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, spp., Such as Heterodera glycines Heterodera shachtoi etc.; US 9,089,135 B2 11 12 Aphelenchoides spp., for example Aphelenchoides besseyi, ducks, geese and bees, other pets, for example dogs, cats, Aphelenchoides ritzemabosi, Aphelenchoides fragarieae, caged birds and aquarium fish, and also so-called test ani Aphelenchus ssp., for example Aphelenchus avenae, Radop mals, for example hamsters, guinea pigs, rats and mice. By holus ssp. for example Radopholus similis, Tilenchulus ssp., controlling these , cases of death and reduction in for example Tvlenchulus semipenetrans, Rotylenchulus ssp., productivity (for meat, milk, wool, hides, eggs, honey etc.) for example Rotylenchulus reniformis, should be diminished, so that more economic and easier Bursaphelenchus spp., for example Bursaphelenchus xylo animal husbandry is possible by use of the inventive active philus, Aphelenchoides spp., Longidorus spp., Xiphinema ingredient combinations. spp., Trichodorus spp. The inventive active ingredient combinations are used in In addition, the inventive active ingredient combinations 10 the veterinary sector and in animal husbandry in a known are found to be effective for controlling nematodes which manner by enteral administration in the form of, for example, attack humans or , for example roundworm, pin tablets, capsules, potions, drenches, granules, pastes, boluses, worm, filaria, Wuchereri bancrofti, threadworms (convoluted the feed-through process and Suppositories, by parenteral filaria), Gnathostoma etc. administration, for example by injection (intramuscular, Sub Animal Health 15 cutaneous, intravenous, intraperitoneal and the like), The inventive active ingredient combinations are effective implants, by nasal administration, by dermal use in the form, not only against plant, hygiene and stored product pests, but for example, of dipping or bathing, spraying, pouring on and also in the Veterinary sector against animal parasites (ecto spotting on, washing and powdering, and also with the aid of and endoparasites). Such as hard ticks, soft ticks, mange moulded articles containing the active ingredient, such as mites, leafmites, flies (biting and licking), parasitic fly larvae, collars, ear marks, tail marks, limb bands, halters, marking lice, hair lice, feather lice and fleas. These parasites include: devices and the like. From the order of the Anoplurida, for example, Hae When used for livestock, poultry, domestic animals and the matopinus spp., Linognathus spp., Pediculus spp., Phtirus like, the active ingredient combinations can be used as for spp. and Solenopotes spp. mulations (for example powders, emulsions, flowables) com From the order of the Mallophagida and the suborders 25 prising the active ingredients in an amount of 1 to 80% by Amblycerina and Ischnocerina, for example, Trimenopon weight, either directly or after 100 to 10000-fold dilution, or spp., Menopon spp., Trinoton spp., Bovicola spp., Werneck they may be used as a chemical bath. iella spp., Lepikentron spp., Damalina spp., Trichodectes Crops spp. and Felicola spp. The crops to be protected, which have only been described From the order of the Diptera and the suborders Nemato 30 in a general manner, are differentiated and specified below. cerina and Brachycerina, for example, Aedes spp., Anopheles Thus, with regard to use, vegetables are understood to mean, spp., Culex spp., Simulium spp., Eusimulium spp., Phleboto for example, fruit vegetables and flower-heads as vegetables, mus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., for example carrots, bell peppers, chilli peppers, tomatoes, Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota aubergines, cucumbers, cucurbits, courgettes, broad beans, spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea 35 runner beans, bush beans, peas, artichokes, maize; spp., Stomoxys spp., Haematobia spp., Morelia spp., Fannia but also leafy vegetables, for example lettuce, chicory, spp., Glossina spp., Caliphora spp., Lucilia spp., Chry endives, cress, rocket salad, field salad, iceberg lettuce, leek, somyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spinach, Swiss chard; spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., additionally tuber vegetables, root vegetables and stem Veg Lipoptena spp. and Mellophagus spp. 40 etables, for example celeriac, beetroot, carrots, garden radish, From the order of the Siphonapterida, for example, Pulex horseradish, Salsify, asparagus, table beet, palm shoots, bam spp., Ctenocephalides spp., Xenopsylla spp. and Ceratophyl boo shoots, and also bulb Vegetables, for example onions, lus spp. leek, fennel, garlic; From the order of the Heteropterida, for example, Cimex additionally brassica vegetables, such as cauliflower, broc spp., Triatoma spp., Rhodnius spp. and Panstrongylus spp. 45 coli, kohlrabi, red cabbage, white cabbage, green cabbage, From the order of the Blattarida, for example, Blatta ori Savoy cabbage, brussels sprouts, chinese cabbage. entalis, Periplaneta americana, Blattella germanica and With regard to use, perennial crops are understood to mean Supella spp. fruit, for example oranges, grapefruit, mandarins, lem From the subclass of the Acari (Acarina) and the orders of ons, limes, bitter oranges, kumquats, satsumas; the Meta- and Mesostigmata, for example, Argas spp., Orni 50 but also pome fruit, for example , and quince, and thodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., stone fruit, for example peaches, nectarines, cherries, plums, Boophilus spp., Dermacentor spp., Haemophysalis spp., common plums, apricots; Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., additionally grapevine, hops, olives, tea, soya, rape, cotton, Raillietia spp., Pneumonyssus spp., Stenostoma spp., Varroa Sugar cane, beet, potatoes, tobacco and tropical crops, for spp. 55 example mangoes, papayas, figs, pineapples, dates, bananas, From the order of the Actinedida (Prostigmata) and Acari durians, kakis, coconuts, cacao, coffee, avocados, lychees, dida (Astigmata), for example, Acarapis spp., Cheyletiella maracujas, guavas, spp., OrnithOcheyletia spp., Myobia spp., Psorergates spp., and also almonds and nuts, for example hazelnuts, walnuts, Demodex spp., Trombicula spp., Listrophorus spp., Acarus pistachios, cashew nuts, brazil nuts, pecan nuts, butter nuts, spp., Trophagus spp., Caloglyphus spp., Hypodectes spp., 60 chestnuts, hickory nuts, macadamia nuts, peanuts, Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes and additionally also soft fruit, for example blackcurrants, spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., gooseberries, raspberries, blackberries, blueberries, straw Cytodites spp. and Laminosioptes spp. berries, red bilberries, kiwis, cranberries. The inventive active ingredient combinations are also Suit With regard to use, ornamental plants are understood to able for controlling arthropods which attack agricultural pro 65 mean annual and perennial plants, for example cut flowers, ductive livestock, for example cattle, sheep, goats, horses, for example , carnations, gerbera, lilies, marguerites, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, chrysanthemums, tulips, daffodils, anemones, poppies, ama US 9,089,135 B2 13 14 ryllis, dahlias, azaleas, malves, but also, for example, bedding the important crop plants, such as cereals (wheat, rice), plants, potted plants and shrubs, for example roses, tagetes, maize, soyabeans, potatoes, cotton, oilseed rape and also fruit pansies, geraniums, fuchsias, hibiscus, chrysanthemums, plants (with the fruits apples, pears, citrus fruits and grapes), busy lizzies, cyclamen, african violets, Sunflowers, begonias, and particular emphasis is given to maize, soya beans, pota in ornamental lawns, in golf lawns, but also in cereals such as toes, cotton and oilseed rape. Traits that are particularly barley, wheat, rye, triticale, oats, in rice, in millet and Sor emphasized are the increased defence of the plants against ghum, in maize, insects by toxins formed in the plants, in particular those additionally, for example, bushes and conifers, for example formed in the plants by the genetic material from Bacillus fig trees, , spruce trees, fir trees, pine trees, yew Thuringiensis (for example by the genes CryIA(a), CryIA(b), trees, juniper trees, stone pines, bays. 10 CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, With regard to use, spices are understood to mean annual Cry3Bb and CryIF and also combinations thereof) (herein and perennial plants, for example aniseed, chilli pepper, bell below referred to as “Bt plants'). Traits that are furthermore pepper, pepper, Vanilla, marjoram, thyme, cloves, juniperber particularly emphasized are the increased tolerance of the ries, cinnamon, tarragon, coriander, Saffron, ginger. plants to certain herbicidally active ingredients, for example According to the invention, it is possible to treat all plants 15 imidazolinones, Sulphonylureas, ACCases, glyphosate or and plant parts. Plants are understood here to mean all plants phosphinotricin (for example the "PAT gene). The genes in and plant populations such as desired and undesired wild question which impart the desired traits can also be present in plants or crop plants (including naturally occurring crop combination with one another in the transgenic plants. plants). Crop plants may be plants which can be obtained by Examples of “Bt plants’ which may be mentioned are maize conventional breeding and optimization methods or by bio varieties, cotton varieties, soya bean varieties and potato vari technological and genetic engineering methods or combina eties which are sold under the trade names YIELD GARDR) tions of these methods, including the transgenic plants and (for example maize, cotton, Soya beans), KnockCut(R) (for including the plant cultivars which can and cannot be pro example maize), StarLink R. (for example maize), Bollgard(R) tected by plant breeders' certificates. (cotton), Nucotnr (cotton) and New Leaf R (potato). GMOS 25 Examples of herbicide-tolerant plants which may be men In a further preferred embodiment, transgenic plants and tioned are maize varieties, cotton varieties and Soya bean plant cultivars which have been obtained by genetic engineer varieties which are sold under the trade names Roundup ing methods, if appropriate in combination with conventional Ready R (tolerance to glyphosate, for example maize, cotton, methods (Genetically Modified Organisms), and parts soya bean), Liberty Link. R (tolerance to phosphinotricin, for thereof are treated. The terms “parts” and “plant parts” have 30 example oilseed rape), IMIR (tolerance to imidazolinones) been explained above. and STS(R) (tolerance to sulphonylureas, for example maize). More preferably, plants of the plant cultivars which are in Herbicide-resistant plants (plants bred in a conventional man each case commercially available or in use are treated in ner for herbicide tolerance) which may be mentioned include accordance with the invention. the varieties sold under the name Clearfield(R) (for example Depending on the plant species or plant cultivars, their 35 maize). Of course, these statements also apply to plant culti location and growth conditions (soils, climate, vegetation vars having these or still-to-be-developed genetic traits, period, diet), the treatment in accordance with the invention which plant cultivars will be developed and/or marketed in may also result in superadditive (“synergistic) effects. For the future. example, reduced application rates and/or a widening of the The plants listed can be treated in accordance with the activity spectrum and/or an increase in the activity of the 40 invention in a particularly advantageous manner with the Substances and compositions which can be used in accor inventive active ingredient mixture. The preferred ranges dance with the invention, better plant growth, increased tol stated above for the mixtures also apply to the treatment of erance to high or low temperatures, increased tolerance to these plants. Particular emphasis is given to the treatment of drought or to water or soil salt content, increased flowering plants with the mixture specifically mentioned in the present performance, easier harvesting, accelerated maturation, 45 text. higher harvest yields, better quality and/or a higher nutri The control of phytopathogenic fungi or animal pests, tional value of the harvested products, better storage stability especially of nematodes, by treating the seed of plants has and/or processibility of the harvested products are possible been known for a long time and is the Subject of continuous which exceed the effects which were actually to be expected. improvements. However, in the treatment of seed, a number The transgenic plants or plant cultivars (i.e. those obtained 50 of problems are encountered which cannot always be by genetic engineering) which are preferred and to be treated resolved in a satisfactory manner. Thus, it is desirable to in accordance with the invention include all plants which, develop methods for protecting the seed and the germinating through the genetic modification, received genetic material plant which significantly reduce, or make Superfluous, the which imparts particular advantageous useful traits to these additional application of crop protection agents after sowing plants. Examples of Such traits are better plant growth, 55 or after the emergence of the plants. It is additionally desir increased tolerance to high or low temperatures, increased able to optimize the amount of active ingredient employed in tolerance to drought or to water or soil salt content, increased Sucha way as to provide maximum protection for the seed and flowering performance, easier harvesting, accelerated matu the germinating plant from attack by phytopathogenic fungi ration, higher harvest yields, better quality and/or a higher or animal pests, especially nematodes, but without damaging nutritional value of the harvested products, better storage 60 the plant itself by the active ingredient used. In particular, stability and/or processibility of the harvested products. Fur methods for the treatment of seed should also take into con ther and particularly emphasized examples of such properties sideration the intrinsic fungicidal properties of transgenic area better defence of the plants againstanimal and microbial plants in order to achieve optimum protection of the seed and pests, such as against insects, mites, nematodes, phytopatho the germinating plant with a minimum of crop protection genic fungi, bacteria and/or viruses, and also increased toler 65 agents being employed. ance of the plants to certain herbicidally active ingredients. The present invention therefore also relates especially to a Examples of transgenic plants which may be mentioned are method for the protection of seed and germinating plants US 9,089,135 B2 15 16 from attack by phytopathogenic fungi or animal pests, espe lecithins and synthetic phospholipids can be used in the for cially by nematodes, by treating the seed with an inventive mulations. Other possible additives are mineral and vegetable composition. oils. The invention likewise relates to the use of the inventive It is possible to use dyes such as inorganic pigments, for compositions for the treatment of seed for protecting the seed example iron oxide, titanium oxide and Prussian Blue, and and the germinating plant from phytopathogenic fungi or organic colorants such as alizarin dyes, azo dyes and metal animal pests, especially from nematodes. phthalocyanine dyes, and trace nutrients such as salts of iron, The invention further relates to seed which has been treated manganese, boron, copper, cobalt, molybdenum and zinc. with an inventive composition for protection from phyto The formulations generally contain between 0.1 and 95% 10 by weight of active ingredient, preferably between 0.5 and pathogenic fungi or animal pests, especially nematodes. 90%. One of the advantages of the present invention is that the The inventive active ingredient combinations may be particular systemic properties of the inventive compositions present in commercially standard formulations and in the use mean that treatment of the seed with these compositions not forms, prepared from these formulations, as a mixture with only protects the seed itself, but also the resulting plants after 15 other active ingredients, such as insecticides, attractants, Ste emergence, from phytopathogenic fungi. In this manner, the rilants, bactericides, acaricides, nematicides, fungicides, immediate treatment of the crop at the time of Sowing or growth-regulating Substances or herbicides. The insecticides shortly thereafter can be dispensed with. include, for example, phosphates, carbamates, carboxylates, It is also considered to be advantageous that the inventive chlorinated hydrocarbons, phenylureas and Substances pro mixtures can also be used for transgenic seed in particular. duced by microorganisms, interalia. Formulations Mixing with other known active ingredients such as herbi The active ingredient combinations can be converted to the cides or with fertilizers and growth regulators is also possible. customary formulations such as Solutions, emulsions, wet When used as insecticides, the inventive active ingredient table powders, Suspensions, powders, dusts, pastes, soluble combinations may additionally be present in their commer powders, granules, Suspension-emulsion concentrates, natu 25 cially available formulations and in the use forms, prepared ral and synthetic materials impregnated with active ingredi from these formulations, as a mixture with Synergists. Syn ent, and microencapsulations in polymeric materials for the ergists are compounds which enhance the action of the active foliar and Soil applications. ingredients, without it being necessary for the Synergist added These formulations are produced in a known manner, for to be active itself. 30 The active ingredient content of the use forms prepared example by mixing the active ingredients with extenders, that from the commercially available formulations may vary is, liquid solvents and/or solid carriers, optionally with the use within widelimits. The active ingredient concentration of the of Surfactants, that is, emulsifiers and/or dispersants, and/or use forms may be from 0.0000001 to 95% by weight of active foam formers. ingredient, preferably between 0.0001 and 50% by weight. If the extender used is water, it is also possible, for 35 The compounds are employed in a customary manner example, to use organic solvents as cosolvents. The following appropriate for the use forms. are essentially suitable as liquid solvents: aromatics such as Use Forms Xylene, toluene or alkylnaphthalenes, chlorinated aromatics Foliar Applications or chlorinated aliphatic hydrocarbons such as chloroben Foliar application is understood to mean the inventive Zenes, chloroethylenes or methylene chloride, aliphatic 40 treatment of the plants and plant parts with the active ingre hydrocarbons such as cyclohexane or paraffins, for example dients directly or by action on the environment, habitat or mineral oil fractions, mineral and vegetable oils, alcohols storage space thereof by the customary treatment methods, Such as butanol or glycol and their ethers and esters, ketones for example by dipping, spraying, vaporizing, nebulizing, Such as acetone, methyl ethyl ketone, methyl isobutyl ketone scattering, painting and injecting. Plant parts are understood or cyclohexanone, strongly polar solvents such as dimethyl 45 to mean all above-ground and below-ground parts and organs formamide and dimethyl sulphoxide, or else water. of plants, such as shoot, leaf flower and root, examples Useful solid carriers are: including leaves, needles, stems, stalks, flowers, fruit-bodies, for example ammonium salts and ground natural minerals fruits and seeds, and also roots, tubers and rhizomes. The Such as kaolins, clays, talc, chalk, quartz, attapulgite, mont plant parts also include harvested plants and vegetative and morillonite ordiatomaceous earth, and ground synthetic min 50 generative propagation material, for example seedlings, erals such as highly disperse silica, alumina and silicates; tubers, rhizomes, cuttings and seeds. Suitable solid carriers for granules are: for example crushed Soil Application and fractionated natural rocks such as calcite, marble, pum Soil application is understood to mean the control of ice, Sepiolite and dolomite, or else synthetic granules of inor insects and/or spider mites and/or nematodes by drenching ganic and organic meals, and granules of organic material 55 pesticides onto the soil, incorporating them into the soil and in Such as sawdust, coconut shells, maize cobs and tobacco irrigation systems as droplet application onto the soil. Alter stalks; suitable emulsifiers and/or foam formers are: for natively, the inventive active ingredient combinations can be example nonionic and anionic emulsifiers such as polyoxy introduced into the site of the plants in solid form (for ethylene fatty acid esters, polyoxyethylene fatty alcohol example in the form of granules). In the case of paddy rice ethers, for example alkylaryl polyglycol ethers, alkylsulpho 60 crops, this may also be accomplished by metering the inven nates, alkyl Sulphates, arylsulphonates, or else protein tive active ingredient combinations in a solid application form hydrolysates; Suitable dispersants are: for example lignoSul (for example as a granule) into a flooded paddy field. phite waste liquors and methylcellulose. The invention relates to these application forms to natural Tackifiers such as carboxymethylcellulose and natural and (soil) or artificial Substrates (for example rock wool, glass synthetic polymers in the form of powders, granules or lati 65 wool, quartz sand, pebbles, expanded clay, Vermiculite), out ces, such as gum arabic, polyvinyl alcohol and polyvinyl doors or in closed systems (e.g. greenhouses or under film acetate, or else natural phospholipids such as cephalins and cover) and in annual (e.g. vegetables, potatoes, cotton, beet, US 9,089,135 B2 17 18 ornamental plants) or perennial crops (e.g. citrus plants, fruit, are soluble in water, may be used. Examples of dyes include tropical crops, spices, nuts, vines, conifers and ornamental those known by the names Rhodamine B, C.I. Pigment Red plants). It is additionally possible to deploy the active ingre 112 and C.I. Solvent Red 1. dients by the ultra-low-volume method or to inject the active The wetters which may be present in the seed dressing ingredient formulation or the active ingredient itself into the product formulations usable in accordance with the invention soil. are all substances which are conventionally used for the for Seed Treatment mulation of active agrochemical ingredients and for promot The inventive active ingredient combinations are suitable ing wetting. Alkylnaphthalenesulphonates, such as diisopro especially for protection of seed of any plant variety which is pyl- or diisobutylnaphthalenesulphonates, can be used with 10 preference. used in agriculture, in greenhouses, in forests or in gardening Useful dispersants and/or emulsifiers which may be from the aforementioned animal pests, especially from nema present in the seed dressing product formulations usable in todes. More particularly, the seed is that of cereals (such as accordance with the invention are all nonionic, anionic and wheat, barley, rye, millet and Sorghum, and oats), maize, cationic dispersants which are conventionally used for the cotton, soya, rice, potatoes, Sunflower, beans, coffee, beet 15 formulation of active agrochemical ingredients. Nonionic or (e.g. Sugar beet and fodder beet), peanut, vegetables (such as anionic dispersants or mixtures of nonionic or anionic dis tomato, cucumber, onions and lettuce), lawns and ornamental persants can be used with preference. Suitable nonionic dis plants. Of particular significance is the treatment of the seed persants include, in particular, ethylene oxide?propylene of cereals (such as wheat, barley, rye and oats), maize and oxide block polymers, alkylphenol polyglycol ethers and rice, and the treatment of cotton and Soya seed. tristryrylphenol polyglycol ethers, and their phosphated or In the context of the present invention, the inventive com Sulphated derivatives. Suitable anionic dispersants are, in par position is applied on its own or in a Suitable formulation to ticular, lignoSulphonates, polyacrylic acid salts and arylsul the seed. Preferably, the seed is treated in a state in which it is phonate? formaldehyde condensates. Sufficiently stable that the treatment does not cause any dam The antifoams which may be present in the seed dressing age. In general, treatment of the seed may take place at any 25 product formulations usable in accordance with the invention point in time between harvesting and Sowing. Typically, the are all foam-Suppressing Substances conventionally used for seed used has been separated from the plant and freed from the formulation of active agrochemical ingredients. Silicone cobs, shells, stalks, coats, hairs or the flesh of the fruits. For antifoams and magnesium Stearate can be used with prefer example, it is possible to use seed which has been harvested, CCC. 30 The preservatives which may be present in the seed dress cleaned and dried to a moisture content of less than 15% by ing product formulations usable inaccordance with the inven weight. Alternatively, it is also possible to use seed which, tion are all substances which can be employed in agrochemi after drying, has been treated, for example, with water and cal compositions for Such purposes. Examples include then dried again. dichlorophene and benzyl alcohol hemiformal. When treating the seed, it generally has to be ensured that 35 The secondary thickeners which may be present in the seed the amount of the inventive composition applied to the seed dressing product formulations usable in accordance with the and/or the amount of further additives is selected such that the invention are all Substances which can be employed in agro germination of the seed is not adversely affected, and that the chemical compositions for Such purposes. Cellulose deriva resulting plant is not damaged. This must be borne in mind in tives, acrylic acid derivatives, Xanthan, modified clays and particular in the case of active ingredients which may exhibit 40 finely divided silica are preferred. phytotoxic effects at certain application rates. The adhesives which may be present in the seed dressing The inventive active ingredient combinations/composi product formulations usable in accordance with the invention tions can be applied directly, i.e. without comprising any are all customary binders which can be employed in seed further components and without having been diluted. In gen dressing products. Preference is given to polyvinylpyrroli eral, it is preferable to apply the compositions to the seed in 45 done, polyvinyl acetate, polyvinyl alcohol and tylose. the form of a suitable formulation. Suitable formulations and The gibberellins which may be present in the seed dressing methods for the treatment of seed are known to the person product formulations usable in accordance with the invention skilled in the art and are described, for example, in the fol are preferably the gibberellins A1, A3 (gibberellic acid), A4 lowing documents: U.S. Pat. No. 4,272.417 A, U.S. Pat. No. and A7, particular preference being given to using gibberellic 4,245,432 A, U.S. Pat. No. 4,808,430 A, U.S. Pat. No. 5,876, 50 acid. The gibberellins are known (cf. R. Wegler “Chemie der 739A, US 2003/0176428 A1, WO 2002/080675 A1, WO Pflanzenschutz- and Schädlingsbekämpfungsmittel Chem 2002/028.186 A2. istry of Plant Protectants and Pesticides, Vol. 2, Springer The active ingredient combinations usable in accordance Verlag, 1970, pp. 401-412). with the invention can be converted to the customary seed The seed dressing product formulations usable in accor dressing product formulations such as solutions, emulsions, 55 dance with the invention can be employed either directly or Suspensions, powders, foams, slurries and other coating com after preceding dilution with water for the treatment of a wide positions for seed, and ULV formulations. range of seeds. For instance, the concentrates or the formu These formulations are prepared in the known manner by lations obtainable therefrom by dilution with water can be mixing the active ingredients or active ingredient combina used to dress the seed of cereals, such as wheat, barley, rye, tions with customary additives, for example customary 60 oats and triticale, and the seed of maize, rice, rape, peas, extenders and also solvents or diluents, dyes, wetters, dispers beans, cotton, soya, Sunflowers and beet, or elsea wide vari ants, emulsifiers, antifoams, preservatives, secondary thick ety of different vegetable seeds. The seed dressing product eners, adhesives, gibberellins, and also water. formulations usable in accordance with the invention or the The dyes which may be present in the seed dressing prod dilute preparations thereof can also be used to dress seed of uct formulations usable in accordance with the invention are 65 transgenic plants. In this context, additional Synergistic all dyes which are customary for Such purposes. Both pig effects may also occur as a consequence of the interaction ments, which are sparingly soluble in water, and dyes, which with the substances formed by expression. US 9,089,135 B2 19 20 Useful apparatus which can be used to treat seed with the means that no galls were found: 0% means that the number of seed dressing product formulations usable in accordance with galls found on the roots of the treated plants was equal to that the invention, or with the preparations prepared therefrom by in untreated control plants. addition of water, is all mixing apparatus which can typically In this test for example, the following combination shows be used to dress seed. Specifically, the seed dressing proce 5 a Superior effect compared to the single compounds. dure is to place the seed into a mixer, add the amount of seed dressing product formulation desired in each case, either as TABLE 1 Such or after preceding dilution with water, and mix the contents of the mixer until the formulation has been distrib Meloidogyne incognita - Test 10 uted homogeneously on the seed. If appropriate, this is fol Concentration Mortality lowed by a drying process. Active Ingredient in ppm in % after 21 The application rate of the seed dressing product formula Fluopyram O.12S 56 tions usable in accordance with the invention can be varied Cyazypyr 4 6 obs.* cal.** within a relatively wide range. It is guided by the particular 15 content of the active ingredients in the formulations and by Fluopyram + Cyazypyr O.125 - 4 68 58.64 the seed. The application rates of the active ingredient com According to the invention binations are generally between 0.001 and 50g per kilogram *obs. = observed insecticidal efficacy of seed, preferably between 0.01 and 25 g per kilogram of **cal. = efficacy calculated with Colby-formula seed.

BIOLOGICAL, EXAMPLES The invention claimed is: 1. A nematicidal active ingredient composition comprising The expected efficacy of a given combination of two com a synergistically effective amount of: pounds is calculated as follows (see Colby, S.R., "Calculat 25 (I) N-2-3-chloro-5-(trifluoromethyl)-2-pyridinyl ing Synergistic and antagonistic Responses of Herbicide ethyl-2-trifluoromethyl-benzamide (I-1) Combinations', Weeds 15, pp. 20-22, 1967): or an N-oxide thereof, and If (II) at least one insecticidal or nematicidal active ingredient X is the efficacy expressed in % mortality of the untreated Selected from the group consisting of Bacillus firmus, control for test compound A at a concentration of m ppm 30 Metarhizium, 4-(6-chloropyrid-3-yl)methyl(2,2-dif respectively mg/ha, luoroethyl)aminofuran-2(5H)-one, cyazypyr, and Y is the efficacy expressed in % mortality of the untreated 5-chloro-2-(3,4,4-trifluorobut-3-en-1-yl)sulphonyl-1, control for test compound B at a concentration of n ppm 3-thiazole. respectively ng/ha, 2. The composition according to claim 1 wherein the insec 35 ticidal or nematicidal active ingredient (II) is selected from E is the efficacy expressed in % mortality of the untreated the group consisting of Bacillus firmus, Metarhizium, and control using the mixture of A and B at m and n ppm 4-(6-chloropyrid-3-yl)methyl(2,2-difluoroethyl) respectively m and ng/ha, aminofuran-2(5H)-one. then is 3. A method for controlling animal pests, comprising 40 allowing the composition as defined in claim 1 to act on the leaves, flowers, stem or the seed of the plants to be protected, on animal pests, the habitat thereof, the soil, or combinations thereof. 4. A process for producing insecticidal, acaricidal, nemati If the observed insecticidal efficacy of the combination is 45 cidal compositions, or combinations thereof, comprising higher than the one calculated as “E”, then the combination of mixing the composition as defined in claim 1 with one or the two compounds is more than additive, i.e., there is a more extenders, Surfactants, or combinations thereof. synergistic effect. 5. Seed comprising the composition as defined in claim 1. 6. A method for controlling animal pests, comprising Example A 50 allowing the composition as defined in claim 1 to act on seed. 7. A method for controlling animal pests, comprising Meloidogyne incognita Test (MELGIN) allowing the composition as defined in claim 1 to act on Soil or artificial substrates. 8. A method according to claim3, wherein the animal pests Solvent: 7 parts by weight of dimethylformamide 55 are nematodes. Emulsifier: 1 parts by weight of alkylarylpolyglycolether 9. The method of claim 8, wherein said at least one insec ticidal or nematicidal active ingredient (II) is cyaZypyr. To produce a suitable preparation of active compound, 1 10. The method of claim 9, wherein the weight ratio of the part by weight of active compound is mixed with the stated compound I-1 to cyazypyr is from 125:1 to 1:125. amount of Solvent, and the concentrate is diluted with emul 60 11. The method of claim 10, wherein the weight ratio of the sifier-containing water to the desired concentration. compound I-1 to cyazypyr is from 25:1 to 1:25. Vessels are filled with sand, a solution of the active ingre 12. The method of claim 10, wherein the weight ratio of the dient, a Suspension containing eggs and larvae of Meloid compound I-1 to cyazypyr is 1:32. ogyne incognita and salad seeds. The salad seeds germinate 13. The composition of claim 1, wherein said at least one and the seedlings grow. Galls develop on the roots. 65 insecticidal or nematicidal active ingredient (II) is cyaZypyr. After the specified period the nematicidal activity is deter 14. The composition of claim 13, wherein the weight ratio mined on the basis of the percentage of gall formation. 100% of the compound I-1 to cyazypyr is from 125:1 to 1:125. US 9,089,135 B2 21 22 15. The composition of claim 14, wherein the weight ratio 22. The composition of claim 17, wherein the weight ratio of the compound I-1 to cyazypyr is from 25:1 to 1:25. of the compound I-1 to Bacillus firmus is from 25:1 to 1:25. 23. The composition of claim 18, wherein the weight ratio 16. The composition of claim 15, wherein the weight ratio of the compound I-1 to 4-(6-chloropyrid-3-yl)methyl(2.2- of the compound I-1 to cyaZypyr is 1:32. difluoroethyl)aminofuran-2(5H)-one is from 125:1 to 17. The composition of claim 1, wherein said at least one 1:125. insecticidal or nematicidal active ingredient (II) is Bacillus 24. The composition of claim 18, wherein the weight ratio firmus. of the compound I-1 to 4-(6-chloropyrid-3-yl)methyl(2.2- 18. The composition of claim 1, wherein said at least one difluoroethyl)aminofuran-2(5H)-one is from 25:1 to 1:25. insecticidal or nematicidal active ingredient (II) is 4-(6- 25. The composition of claim 19, wherein the weight ratio chloropyrid-3-yl)methyl(2,2-difluoroethyl)aminofuran-2 10 of the compound I-1 to 5-chloro-2-(3,4,4-trifluorobut-3-en (5H)-one. 1-yl)sulphonyl-1,3-thiazole is from 125:1 to 1:125. 19. The composition of claim 1, wherein said at least one 26. The composition of claim 19, wherein the weight ratio insecticidal or nematicidal active ingredient (II) is 5-chloro of the compound I-1 to 5-chloro-2-(3,4,4-trifluorobut-3-en 2-(3,4,4-trifluorobut-3-en-1-yl)sulphonyl-1,3-thiazole. 15 1-yl)sulphonyl-1,3-thiazole is from 25:1 to 1:25. 20. The composition of claim 1, wherein said at least one 27. The composition of claim 20, wherein the weight ratio insecticidal or nematicidal active ingredient (II) is Metarhi of the compound I-1 to Metarhizium is from 125:1 to 1:125. Zium. 28. The composition of claim 20, wherein the weight ratio 21. The composition of claim 17, wherein the weight ratio of the compound I-1 to Metarhizium is from 25:1 to 1:25. of the compound I-1 to Bacillus firmus is from 125:1 to 1:125. k k k k k