NEMATICIDAL COMPOSITIONS

Abstract

The present invention relates to the use of N-methoxy(phenylethyl)-pyrazole carboxamides for the control of nematodes in agriculture and as antihelminthic agents against endoparasites in animals and humans, as well as compositions comprising such compounds. The present invention further relates to the use of these compounds or compositions for controlling nematodes and/or helminths, in particular for controlling plant parasitic nematodes, and to the use of these compounds in preparing nematicidal and/or antihelminthic compositions.

Claims

1-12. (canceled)

13. A method of controlling infestation of a useful plant by a plant parasitic nematode, said method comprising applying to the plant seed of the useful plant prior to planting, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide wherein 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide at a rate of 0.0375 to 0.15 mg per seed.

14. The method of claim 13, wherein the 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide is applied at a rate of 0.0375 mg per seed, 0.075 mg per seed, or 0.15 mg per seed.

15. The method of claim 13, wherein the 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide is in the form of a slurry of particles in aqueous medium.

16. The method of claim 15, wherein the concentration of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide in the aqueous slurry of particles is from 5% (w/w) to 40% (w/w).

17. The method of claim 13, wherein the plant seed is a soybean plant seed.

18. The method of claim 13, wherein the plant parasitic nematode is selected from the group consisting of the following species: Heterodera and Meloidogyne.

Description

EXAMPLES

[0073] Soybean Cyst Nematode (Heterodera glycines) on Soybean
Methodology for evaluating control of Heterodera glycines at all life stages on soybean in a greenhouse.
Five thousand Heterodera glycine eggs where placed in a 1 inch hole in the center of 3.5 inch×8 inch deep plastic pots. The seeds were inoculated first when applying the active compound as a seed treatment. The treated seed was placed in the center hole and covered up with sterilized top soil. Each pot was watered by hand, with approximately 50 mls of water applied to each pot once per day. 35 day after planting, the soil was gently rinsed from the roots of the emerged plants and place in a 20 mesh over a 60-mesh sieve. The root system was blasted with waterto remove mature females. The 20-mesh sieve removed. The females were washed to the bottom ofthe 60-mesh sieve and rinsed into a tube for counting under a stereoscope. For root penetration experiments, the roots of the plants were removed from the pots at 7-14 days after planting, rinsed clean of soil, and stained with acid fuchsin stain. Stained nematodes in the roots were counted using an electronic stereoscope.

Series 1 Trials

[0074]

TABLE-US-00001 Trial 1: Treatment Stained (Pydiflumetofen Juveniles Mature Cysts per Number mg ai/seed) w/I root SCN Cysts Gram of Root 1 Untreated 30.0 28.0 213.6 2 0.0375 22.5 24.0 147.9 3 0.075 19.0 21.3 167.5 4 0.15 12.5 16.3 105.0 Trial 2: Treatment Soybean Cyst (Pydiflumetofen SCN Within Nematodes per Number mg ai/seed) Root Gram of Root 1 Check 23.3 167 2 0.075 17.5 128 3 0.15 5.0 29.6 Trial 3: Treatment (Pydiflumetofen SCN Cysts Number mg ai/seed) per Root 1 Check 18.3 2 0.15 10.4 3 0.30 5.5 Yield Data Mean Difference in Yield Compared to Checks§ (Bu/Ac) Fluopyram Pydiflumetofen Trial (0.15 mg ai/seed) (0.075 mg ai/seed) 4 −3.5 +3.0 5 +5.4 +3.7 6 +2.9 +7.5 Evaluation of Soybean Cyst Nematode (Heterodera glycines) Egg Hatch Concentration Percent Egg Treatment (ppm) Hatch Reduction Untreated Check — Fluopyram 100 61.9 Fluopyram 10 4.5 Fluopyram 1 −1.3 Pydiflumetofen 100 64.0 Pydiflumetofen 10 34.7 Pydiflumetofen 1 4.7 Fluensulfone 100 0.5 Fluensulfone 10 −1.5 Fluensulfone 1 −2.1 Tioxazafen 100 −0.9 Tioxazafen 10 −0.5 Tioxazafen 1 0.4 Burkholderia spp. 100 1.7 Burkholderia spp. 10 0.0 Burkholderia spp. 1 −1.6 Bacillus amyloliquefaciens 100 1.7 Bacillus amyloliquefaciens 10 2.5 Bacillus amyloliquefaciens 1 −0.8 Sodium hypochlorite 30% 100.0

Series 2 Trials

[0075] The action of pydiflumetofen against soybean syst nematode (SCN; Heterodera glycines) and its effect on soybean plants was assessed out as described previously, and compared to that of fluopyram. The number of SCN per stained root was counted, and the mean root weight per plant calculated, thus enabling the number of SCN per gram of root to be calculated.

TABLE-US-00002 Trial 1 Treatment Mean Root mass No. SCN/ (mg ai/seed) SCN/ mean/ g root Test Pydiflumetofen Fluopyram root plant (g) tissue 1 — — 67.2 1.5 57.6 2 0.075 — 52.3 1.8 30.4 3 0.15 — 37.0 2.2 16.9 4 0.30 — 35.2 2.3 15.2 5 — 0.075 20.8 1.8 12.1 6 — 0.15 17.7 0.6 30.3 7 — 0.30 7.3 0.5 23.4
Root Knot Nematode (Meloidogyne incognita)

Methodology for Evaluating Root Knot Nematode Gall Count and Rating Process

[0076] The roots of the plants were removed from the soil. The root system was then sprayed with water to remove remaining soil. The roots were spread out on a tray or counter top and the rate of galling or place each root system under a magnification light and count galls. For gall assessment ratings, a rating on a scale of 0-10 scale was given when compared against a standard gall rating chart. Gall count was also assessed.
Root Knot Nematode (Meloidogyne incognita) Control—Soybean

TABLE-US-00003 Treatment Root Knot Root Knot (Pydiflumetofen Nematode Galling Nematode mg ai/seed) (0-10 scale) Galls per Root Untreated 9 47.4 0.075 6.8 52.6 0.15 1.5 11.2
Multiple Nematode Species [Root Knot (Meloidogyne incognita); Spiral (Helicotylenchus spp.) and Reniform Nematode (Rotylenchulus reniformis)]—Cotton

TABLE-US-00004 Juveniles per 100 cc s Soil Pydiflumetofen (0.15 mg ai/seed) - Nematode Specie Check measured 71 days after planting Root Knot 198 132 Spiral 258 254 Reniform (juvenile) 2264 1752 Reniform (adult) 6.8 2.8
Evaluation of Root Knot Nematode (Meloidogyne incognita) Egg Hatch

TABLE-US-00005 Concentration Percent Egg Treatment (ppm) Hatch Reduction Untreated Check — Fluopyram 100 54.7 Fluopyram 10 55.9 Fluopyram 1 1.1 Pydiflumetofen 100 30.6 Pydiflumetofen 10 12.8 Pydiflumetofen 1 1.7 Fluensulfone 100 48.8 Fluensulfone 10 −0.9 Fluensulfone 1 −3.5 Tioxazafen 100 4.4 Tioxazafen 10 −0.8 Tioxazafen 1 −1.9 Burkholderia spp. 100 10.9 Burkholderia spp. 10 3.1 Burkholderia spp. 1 −0.7 Bacillus amyloliquefaciens 100 2.6 Bacillus amyloliquefaciens 10 −1.5 Bacillus amyloliquefaciens 1 2.1 Sodium hypochlorite 30% 100.0
Lesion Nematode (Pratylenchus brachyurus) Efficacy—Soybean
Soybean plant roots were stained using acid fuchsin/methyl blue to assess for endoparasitic, endo/ectoparasitic, and semi endoparasitic nematodes that have entered the root system, using standard methodology.

TABLE-US-00006 Treatment Lesion (Pydiflumetofen Nematodes Lesion Nematode mg ai/seed) w/I root per Gram of Root Untreated 44.7 162.1 0.0375 44.9 164.3 0.075 38.3 141.5 0.15 32.3 105.3
Reniform Nematode (Rotylenchulus reniformis) Efficacy—Soybean
Mean difference in soil nematode count compared to check

TABLE-US-00007 Nematode Reduction Treatment Compared to Check 0.075 mg Pydiflumetofen/seed −2912 0.15 mg Fluopyram/seed −3146 Aldicarb in-furrow (5.6 Kg/Ha) −1937
Lance (Hoplolaimus spp.) and Sting (Belonolaimus longicaudatus) Nematode
In Vitro assay measuring dose response of APN against Sting and Lance Nematode.

TABLE-US-00008 Percentage of Dead Nematodes Exposure Time Pydiflumetofen Concentration Species (hours) Check 0.1 ppm 10 ppm 100 ppm Lance 1 0 12.7 37.9 74.8 Lance 24 0 68.5 81.6 23.9 Lance 48 0 41 d 93.8 74.8 Lance 72 0 32.9 93.8 77.5 Sting 1 0 6.3 5.9 11.3 Sting 24 0 4.7 59.5 42.9 Sting 48 0 29.3 56.3 58 Sting 72 0 34.9 81.1 97.1
Lesion Nematode (Pratylenchus Spp.) Control in Corn (Zea mays)
Corn root tissue was stained using acid fuchsin/methyl blue to assess for endoparasitic, endo I ectoparasitic, and semi endoparasitic nematodes that have entered the root system, using standard methodology. The effect of pydiflumetofen was compared to fluopyram.

TABLE-US-00009 Treatment Lesion Nematodes Lesion Nematode (mg ai/seed) within root system per gram of Root Untreated 830 2,001 0.4 mg Pydiflumetofen 302 389 0.5 mg Pydiflumetofen 124 105 0.25 mg Fluopyram 108 211
Not only did pydiflumetofen reduce nematode numbers, it also resulted in an increase in corn shoot and root mass over that observed for untreated and fluopyram treated corn plants.