Quinoline nematicidal method

Abstract

A method of inhibiting a nematode population which comprises applying to the locus of a nematode, a nematode inactivating amount of a compound of the formula (1):Het--X--CH.sub.2 --CH.sub.2 --Ar (1)or an N-oxide or salt thereof, whereinHet is a nitrogen containing heterocycle, for example 8-fluoroquinazolin-4-yl, or quinoline-4-amine,X is O, NH, or CH.sub.2 ; andAr is a substituted phenyl group, for example 4-(2,2,2-trifluoroethoxy)phenyl.

Description

FIELD OF THE INVENTION

This invention provides a new nematicidal method. There is an acute need for new nematicides and new nematicidal methods, because available nematicides typically have high mammalian toxicity and must be used at high rates. A nematicide that can be applied at lower rates and that has lower mammalian toxicity would represent a significant advance.

SUMMARY OF THE INVENTION

More specifically, this invention provides a method of inhibiting a nematode population which comprises applying to the locus of a nematode, a nematode inactivating amount of a compound of the formula (1):

Het--X--CH.sub.2 --CH.sub.2 --Ar (1) or an N-oxide or salt thereof, wherein Het is a group selected from: ##STR1## X is O, NH, or CH.sub.2 ; Ar is a substituted phenyl group of formula (18), (19), or (20) ##STR2## wherein Y is O or S; R.sup.1 is (C.sub.2 -C.sub.5) alkyl, (C.sub.3 -C.sub.7) branched alkyl, halo (C.sub.1 -C.sub.4) alkyl, phenyl, or phenyl substituted with CF.sub.3, CN or halo; R.sup.2 is H, F, or Cl, or R.sup.2 combines with Y--R.sup.1 to form --CH.sub.2 --CH.sub.2 --O-- or --O--CF.sub.2 --O--; and Z is halo.

DETAILED DESCRIPTION OF THE INVENTION

Throughout this document, all temperatures are given in degrees Celcius, and all percentages are weight percentages unless otherwise stated.

The term "halo" refers to a F, Cl, Br, or I atom.

The term "haloalkyl" refers to straight chain and branched chain groups.

The term "HPLC" refers to a high pressure liquid chromatography.

The term "inhibiting a nematode" refers to a decrease in the numbers of living nematodes.

The term "nematode-inactivating amount" is used to describe the amount, which is sufficient to cause a measurable reduction in the treated nematode population.

The term "peanut root knot nematode assay" refers to the test method described in detail hereinafter.

PREFERED EMBODIMENTS

While the compounds of formula (1) as a class are exceptionally active as nematicides, use of certain subclasses of these compounds is preferred for reasons of greater efficacy. More specifically, use of the following subclasses of compounds is preferred:

a) compounds of formula (1) that provide at least 80% control when tested in the peanut root knot nematode assay at 12 ppm; b) compounds of formula (1) wherein Het is a quinoline group of formula (2); c) compounds of formula (1) wherein Het is an 8-fluoroquinoline group of formula (3); d) compounds of formula (1) wherein Het is a quinazoline group of formula (4); e) compounds of formula (1) wherein Het is an 8-fluoroquinazoline group of formula (5); f) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R.sup.1 is halo(C.sub.1 -C.sub.4)alkyl; g) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R.sup.1 is selected from CF.sub.3, CHF.sub.2, CF.sub.2 CF.sub.3, CH.sub.2 CF.sub.3, CF.sub.2 CHF.sub.2, CH(CH.sub.3)CF.sub.3, CH.sub.2 CF.sub.2 CF.sub.2 H, and CH.sub.2 CF.sub.2 CF.sub.3 ; h) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R.sup.1 is a (C.sub.3 -C.sub.6) branched alkyl group; i) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R.sup.1 is a phenyl group that is substituted with one or more halo or CF.sub.3 groups; j) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R.sup.1 is (C.sub.2 -C.sub.5) alkyl.

Use of the following compounds is particularly preferred due to their extraordinary activity Each was found to give 100% control when tested at a concentration of about 1 ppm in the soil against the peanut root knot nematode.

8-fluoro-4-[2-[4-(difluoromethoxy)phenyl]ethoxy]-quinazoline; 8-fluoro-4-[2-[4-(pentafluoroethoxy)phenyl]ethoxy]-quinoline; 4-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethoxy]quinazoline; 8-fluoro-4-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethoxy]-quinazoline; 8-fluoro-4-[2-[4-[4-(trifluromethyl)phenoxy]phenyl]ethoxy]-quinazoline; 8-fluoro-4-[2-(4-n-pentoxyphenyl)ethoxy]quinazoline; 8-fluoro-N-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethyl]-quazoline-4-amine; 8-fluoro-4-[2-[4-(trifluoromethoxy)phenyl]ethoxy]quinazoline; 4-[2-[4-(4-fluorophenoxy)phenyl]ethoxy]quinazoline; 8-fluoro-4-[2-[4-(t-butoxy)phenyl]ethoxy]quinoline; N-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethyl]quinazolin-4-amine; 5-methyl-N-[2-[4-(trifluoromethyl)phenyl]ethyl]quinazolin-4-amine; N-[2-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]ethyl]-quazolin-4-amine; 8-fluoro-4-[2-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]ethoxy]quinoline; 6-chloro-N-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethyl]quinazolin-4-amine; 4-[2-[4-[4-(trifluromethyl)phenoxy]phenyl]ethoxy]pyrido-[2,3-d]pyrimidine.

Other preferred compounds include 4-[2-[4-(4- and 8-fluoro-4-[2-[4-chlorophenoxy)phenyl]ethoxy]quinazoline. (4-chlorophenoxy)phenyl]ethoxy]quinazoline.

The following table identifies specific compounds of formula (1) wherein Ar is a group of formula (18) or (20) and gives the results of testing them against the peanut root knot nematode, Meloidogyne arenaria, in the peanut root knot nematode assay. The peanut root knot nematode assay is carried out as follows. Each test compound is initially formulated as a 400 ppm solution by combining 19.2 mL of 0.05% solution of Tween 20 (polyoxyethylene (20) sorbitan monolaurate) in water with a solution of 8 mg of the compound in 0.8 mL of acetone/EtOH (9/1). The 400 ppm solution is then diluted with water to give a 200 ppm solution Three to four cucumber seeds are placed in 16 g of clean white sand, and 1 mL of the 200 ppm solution of test compound is added. This provides a concentration of the compound in the soil of 12 ppm. The cups are allowed to dry one to two hours, and then one mL of a concentrated (50 to 60 per mL) nematode (Meloidogyne arenaria) suspension is added to each cup. The cups are incubated for four to seven days. Then 11 mL of deionized water is added to each cup and the cup is gently shaken to rinse the nematodes from the sand. The suspension is poured into a watchglass and observed under a dissecting microscope at 15.times.-20.times.. An activity rating is given based on nematode mortality. Aldicarb, carbofuran, and fenamiphos are used as chemical standard compounds. Results are reported in the last column of the following table.

__________________________________________________________________________ Nematode ResultsExample MP at 12 ppmNo. Het X Y R.sup.1 R.sup.2 .degree.C. % control__________________________________________________________________________1 2 O O 1,1,2,2-tetrafluoroethyl H 70-72 02 2 O O 2,2,2-trifluoroethyl H 65-66 100 1003 2 O O ethyl H 65-66 100 100 100 87.54 2 O O t-butyl H oil 1005 2 O O 1,1-dimethylpropyl H oil 100 906 2 O O 1-ethyl-1-methylpropyl H oil 1007 3 O O 4-chlorophenyl H 130 1008 2 NH O ethyl H 125-126 09 3 O O 1,1,2,2-tetrafluoroethyl H 70-72 100 99.5 7010 3 O O difluoromethyl H 114 100 0 9011 3 O O pentafluoroethyl H 92.5 100 10012 3 O O 2,2,2-trifluoroethyl H 119 100 10013 3 O O trifluoromethyl H 87-89 10014 3 O O 2,2,3,3-tetra- H 75 fluoropropyl15 3 O O 2,2,2-trifluoroethyl F 47-49 10016 3 O O 1-methylethyl H 111-113 017 3 O O n-butyl H 80-82 10018 3 O O t-butyl H 97-98 100 100 10019 3 O O 1,1-dimethylpropyl H oil 100 10020 3 O O 1-ethyl-1-methylpropyl H oil 100 5021 3 O O --CH.sub.2 --CH.sub.2 -- 98.5 100 10022 3 O O n-pentyl H 245 10023 3 O O phenyl H 107 024 3 O O 4-(trifluromethyl)phenyl H 85.9 025 3 O O 2,4-difluorophenyl H 107 100 10026 3 O O 2,4-dichlorophenyl H oil27 3 O O 3-(trifluromethyl)phenyl H oil 028 3 O O 2,2,3,3-tetrafluoro- F oil propyl29 3 O O 2,2,2-trifluoroethyl Cl oil30 3 NH O 1,1,2,2-tetrafluoroethyl H 168-170 10031 3 NH O trifluoromethyl H 198-200 100 10032 3 NH O 2,2,2-trifluoroethyl H 182 6033 3 NH O 2,2,2-trifluoroethyl F 193 100 10034 3 NH O 2,2,3,3-tetrafluoro- H 135 propyl35 3 NH O 2,2,2-trifluoro-1- H 163-165 methylethyl36 3 NH O 2,2,2-trifluoroethyl Cl 19637 3 NH O ethyl H 179-181 038 3 NH O i-propyl H 124-126 039 3 NH O phenyl H 109-111 6040 3 NH O 2,4-difluorophenyl H 168 100 10041 3 NH O 2-fluorophenyl H 192 100 6042 3 NH O 2,4-dichlorophenyl H 11543 3 NH Si(CH.sub.3).sub.3 H 25044 4 O O pentafluoroethyl H 70 100 100 10045 4 O O trifluoromethyl H 44-46 100 97.546 4 O O 2,2,2-trifluoroethyl H 80-83 100 100 10047 4 O O 2,2,2-trifluoroethyl F 73 100 10048 4 O O 1,1,2,2-tetrafluoroethyl H 38-40 100 10049 4 O O difluoromethyl H 67 100 10050 4 O O 2,2,3,3-tetrafluoro- H 85 propyl51 4 O O 2,2,2-trifluoro-1- H oil methylethyl52 4 O O n-propyl H 67-69 99 100 9053 4 O O ethyl H 80-81 100 10054 4 O O i-propyl H 61-66 100 10055 4 O O t-butyl H 62-63 100 10056 4 O O n-butyl H 56-58 0 057 4 O O 1-ethyl-1-methylpropyl H oil 100 97.558 4 O O pentyl H oil 10059 4 O O 4-(t-butyl)phenyl H oil 060 4 O O 4-(trifluoromethyl)- H 53-55 100 phenyl 90 100 10061 4 O O phenyl H oil 10062 4 O O 2-fluorophenyl H oil 9563 4 O O 2,4-difluorophenyl H 86 100 10064 4 O O 4-chlorophenyl H 74 10065 4 O O 2,4-dichlorophenyl H 9466 4 O O 4-cyanophenyl H 123-12567 4 O --O--CF.sub.2 --O--68 4 O S 3-(trifluoromethyl)- H oil69 4 NH O 1,1,2,2-tetrafluoroethyl H 137- 139 100 100 87.5 10070 4 NH O trifluoromethyl H 115-117 100 10071 4 NH O 2,2,2-trifluoroethyl H 156 100 10072 4 NH O 2,2,3,3-tetrafluoro- H 138 propyl73 4 NH O 2,2,2-trifluoro-1- H 162-164 methylethyl74 4 NH O 2,2,2-trifluoroethyl Cl75 4 NH O 2,2,2-trifluoroethyl F 136 100 10076 4 NH O ethyl H 158-160 077 4 NH O i-propyl H 185-187 078 4 NH O 2-fluorophenyl H 146 100 10079 4 NH O phenyl H 126-128 5080 4 NH O 2,4-difluorophenyl H 139 100 10081 4 NH O 4-(trifluoromethyl)- H 137-139 phenyl82 4 NH Si(CH.sub.3).sub.3 H83 5 O O difluoromethyl H 86 100 100 10084 5 O O 2,2,2-trifluoroethyl H 82-84 100 100 100 10085 5 O O trifluoromethyl H 49-51 100 100 10086 5 O O 1,1,2,2-tetrafluoroethyl H 87-89 100 100 10087 5 O O 2,2,3,3-tetrafluoro- H 71 propyl88 5 O O i-propyl H >40 100 10089 5 O O t-butyl H 104-106 100 99.590 5 O O ethyl H 75-76 100 4091 5 O O pentyl H 60-62 100 10092 5 O O 3-(trifluoromethyl)- H oil 100 phenyl 10093 5 O O phenyl H 100-102 10094 5 O O 4-(trifluoromethyl)- H 76- 79 100 phenyl 100 10095 5 O O 2,4-difluorophenyl H 75-7796 5 O O 4-chlorophenyl H 5297 5 O S 3-(trifluoromethyl)- H 102 phenyl98 5 NH O 2,2,2-trifluoroethyl H 177.2 100 100 5599 5 NH O 2,2,2-trifluoroethyl F 174-178 100100 5 NH O 2,2,3,3-tetrafluoro- H 121 propyl101 5 NH O 2,2,2-trifluoro-1- H 145 methylethyl102 5 NH O i-propyl H 147-149 100 95103 5 NH O 3-(trifluoromethyl)- H 134-136 0 phenyl104 5 NH O phenyl H 134-136 100 80 80 80105 5 NH O 2,4-difluorophenyl H 158106 5 CH.sub.2 O ethyl H oil 100 100 100107 6 O O 2,2,2-trifluoroethyl H 101 0108 6 O O 4-(trifluoromethyl)- H 116 0 phenyl109 6 NH O 2,2,2-trifluoroethyl H 150 0110 7 O O 4-(trifluoromethyl)- H 80-82 100 phenyl111 7 NH O 2,2,2-trifluoroethyl H 151 100112 7 O O 2,2,2-trifluoroethyl H 85 100113 7 NH O 4-(trifluoromethyl)- H 218 100 phenyl114 8 NH O 2,2,2-trifluoroethyl H 187 100115 8 O O 2,2,2-trifluoroethyl H 95 0116 9 O O 1,1,2,2-tetrafluoroethyl H 60-62 100 100117 9 O O 2,2,2-trifluoroethyl H 109118 9 O O 4-(trifluoromethyl)- H 95-97 phenyl119 9 NH O 2,2,2-trifluoroethyl H 217120 9 NH O 2,2,3,3-tetrafluoro- H propyl121 10 O O pentafluoroethyl H 94-95 0122 10 O O ethyl H 87-88 0123 10 O O 4-(trifluoromethyl)- H 110-112 0 phenyl124 10 O O phenyl H 110-112 60 60125 10 NH O trifluoromethyl H 166-169 100 80126 10 NH O ethyl H 174-176 0127 11 O O pentafluoroethyl H 79-80 100 100128 11 O O 2,2,2-trifluoroethyl H 73- 74 100129 11 O O difluoromethyl H130 11 O O n-butyl H131 11 O O 4-(trifluoromethyl)- H 106-108 100 phenyl 100 100 100132 11 O O 3-(trifluoromethyl)- H oil 100 phenyl 100133 11 O O phenyl H 60 100 100134 11 O O 4-chlorophenyl H 148-150135 11 NH O trifluoromethyl H 243-249 0136 11 NH O ethyl H 220-222 0 0137 12 NH O phenyl H138 12 NH O 2,2,2-trifluoroethyl H 84-85139 13 NH O trifluoromethyl H 163-164 100 100140 13 NH O 2,2,2-trifluoroethyl H 139-140 100141 13 NH O phenyl H 157-158 0142 14 O O t-butyl H 75 99 97.5 90143 14 O O n-butyl H 60-61 100144 14 NH O ethyl H 164 0145 15 NH Si(CH.sub.3).sub.3 H 133-135146 15 NH O 1,1,2,2-tetrafluoroethyl H 153-155 100 45147 15 NH O 2,2,2-trifluoroethyl H 149-150 100 97.5148 15 O O 1,1,2,2-tetrafluoroethyl H 41-43 100 100149 15 O O 2,2,2-trifluorethyl H 74-76 100 100150 15 O O 3-(trifluoromethyl)- H 50-60 0 phenyl151 16 NH O 1,1,2,2-tetrafluoroethyl H 145-147 100 100 25 100152 16 NH O 2,2,2-trifluoroethyl H 150-151153 16 NH O ethyl H 155-160 0154 17 O O pentafluoroethyl H 72-74 100 35155 17 NH O 2,2,2-trifluoroethyl H 165-166 0__________________________________________________________________________

The following Table II identifies specific compounds of formula (1) wherein Ar is a group of formula (19) and gives results of testing them in the above described peanut root knot nematode assay.

TABLE II______________________________________ Nematode ResultsExample MP at 12 ppmNo. Het X Z .degree.C. % control______________________________________156 2 O Cl 106-107 0157 2 NH F 121-122158 2 NH Cl 162-163159 3 O Cl 139-140 0160 3 O F 126-127161 3 O Br 130 100 70162 3 NH Br 198-199163 3 NH Cl 176-177 0164 3 NH I 221-223 0165 3 CH.sub.2 Cl 97 0 100166 4 O Cl 57-58 100167 4 O Br 64-65 100168 4 O F 93-94169 4 NH Cl 60170 4 NH Br 190-192 100171 4 NH F 171-173172 5 O Cl 85-87 100173 5 NH Cl 197-200 100174 9 O Cl 88-90 80 75175 10 NH Cl 178.5-180.5176 11 O Cl 126-1281779 11 NH Cl 271-275 0178 12 O Cl 86 0179 13 NH Cl 193-194 100 99.5180 15 NH Cl 189-190 0______________________________________

The compounds of formula (1) are known compounds, or they are made using well known chemical procedures The required starting materials are commercially available, or they are readily synthesized using standard procedures. Compounds of formula (1) wherein Het is of formula (2) or (3) can be synthesized, for example, by the methods disclosed in U.S. Pat. No. 5,114,939, issued May 19, 1992, which is hereby incorporated herein by reference. Compounds wherein Het is of formula (4), (5), (6), (7), (8), or (9) can be synthesized, for example, by the methods disclosed in U.S. patent application Ser. No. 07/324,056, filed Mar. 16, 1989, (pending), corresponding to EPA 326329, which is hereby incorporated herein by reference, Compounds wherein Het is of formula (10), (11), (12), or (13) can be synthesized, for example, by the methods disclosed in U.S. Pat. No. 5,034,393, issued Jul. 23, 1991, which is hereby incorporated herein by reference. Compounds wherein Het is of formula (14) can be synthesized, for example, by the methods disclosed in U.S. patent application Ser. No. 07/502,364 filed Mar. 30, 1990, now U.S. Pat. No. 5,137,879 which is hereby incorporated herein by reference. Compounds wherein Het is of formula, (16), or (17) can be synthesized, for example, by the methods disclosed in U.S. patent application Ser. No. 07/502,342, filed Mar. 30, 1990, (pending), corresponding to EPA 452002 which is hereby incorporated herein by reference

The method of this invention is practiced in accordance with standard techniques for the application of nematicides. In general, good nematicidal activity can be expected at rates of 1-10 lbs/acre.

The compounds of formula (1) are typically applied in the form of nematicide compositions which comprise a compound of formula (1) and a phytologically-acceptable inert carrier. The compositions are either concentrated formulations which are dispersed in water for application, or are dust or granular formulations which are applied without further treatment. The compositions are prepared according to procedures and formulae which are conventional in the agricultural chemical art.

Granular compositions usually contain from about 0.5% to about 15% by weight of the compound, dispersed in an inert carrier which consists entirely or in large part of clay or a similar inexpensive substance. Such compositions are usually prepared by dissolving the compound in a suitable solvent, and applying it to a granular carrier which has been preformed to the appropriate particle size, in the range of from about 0.5 to 3 mm. Such compositions may also be formulated by making a dough or paste of the carrier and compound, and crushing and drying to obtain the desired granular particle size. In use, granules are incorporated into the soil before planting, or applied in the furrow with the seed at planting, or applied in a band on top of a seed row, or broadcast and then incorporated into the soil, or used as a side dressing to an established crop.

Dusts containing the compounds are prepared simply by intimately mixing the compound in powdered form with a suitable dusty agricultural carrier, such as kaolin clay, ground volcanic rock and the like. Dusts can suitably contain from about 1% to about 10% of the compound

Nematicides are also applied as dispersions. For example they can be applied as aqueous drenches around growing plants or applied incrementally via an irrigation system. The dispersions in which the compounds are applied are most often aqueous suspensions or emulsions prepared from concentrated formulations of the compounds. Such water-soluble, water-suspendable or emulsifiable formulations are either solids usually known as wettable powders, or liquids usually known as emulsifiable concentrates or aqueous suspensions. Wettable powders, which may be compacted to form water dispersible granules, comprise an intimate mixture of the active compound, an inert carrier and surfactants. The concentration of the active compound is usually from about 10% to about 90% by weight. The inert carrier is usually chosen from among the attapulgite clays, the montmorillonite clays, the diatomaceous earths, or the purified silicates Effective surfactants, comprising from about 0.5% to about 10% of the wettable powder, are found among the sulfonated lignins, the condensed naphthalenesulfonates, the naphthalenesulfonates, the alkylbenzenesulfonates, the alkyl sulfates, and non-ionic surfactants such as ethylene oxide adducts of alkyl phenols.

Emulsifiable concentrates of the compounds comprise a convenient concentration of a compound, such as from about 50 to about 500 grams per liter of liquid, equivalent to about 5% to about 50%, dissolved in an inert carrier which is either a water miscible solvent or a mixture of water-immiscible organic solvent and emulsifiers. Useful organic solvents include aromatics, especially the xylenes, and the petroleum fractions, especially the high-boiling naphthalenic and olefinic portions of petroleum such as heavy aromatic naphtha. Other organic solvents may also be used, such as the terpenic solvents including rosin derivatives, aliphatic ketones such as cyclohexanone, and complex alcohols such as 2-ethoxyethanol. Suitable emulsifiers for emulsifiable concentrates are chosen from conventional nonionic surfactants, such as those discussed above.

Aqueous suspensions comprise suspensions of water-insoluble compounds of this invention, dispersed in an aqueous vehicle at a concentration in the range from about 5% to about 50% by weight Suspensions are prepared by finely grinding the compound, and vigorously mixing it into a vehicle comprised of water and surfactants chosen from the same types discussed above Inert ingredients, such as inorganic salts and synthetic or natural gums, may also be added, to increase the density and viscosity of the aqueous vehicle It is often most effective to grind and mix the compound at the same time by preparing the aqueous mixture, and homogenizing it in an implement such as a sand mill, ball mill, or piston-type homogenizer.

When applied in the form of a dispersion of the active ingredient in a liquid carrier, it is conventional to refer to application rates in terms of the concentration of active ingredient in the carrier The most widely used carrier is water.

It is equally practical, when desirable for any reason, to apply the compound in the form of a solution in an appropriate organic solvent, usually a bland petroleum oil, such as the spray oils, which are widely used in agricultural chemistry.

The following formulations of compounds of the invention are typical of compositions useful in the practice of the present invention.

______________________________________A. 0.75 Emulsifiable ConcentrateCompound of Formula (1) 9.38%"TOXIMUL D" 2.50%(nonionic/anionic surfactant blend)"TOXIMUL H" 2.50%(nonionic/anionic surfactant blend)"EXXON 200" 85.62%(naphthalenic solvent)B. 1.5 Emulsifiable ConcentrateCompound of Formula (1) 18.50%"TOXIMUL D" 2.50%"TOXIMUL H" 2.50%"EXXON 200" 76.50%C. 1.0 Emulsifiable ConcentrateCompound of Formula (1) 12.50%N-methylpyrrolidone 25.00%"TOXIMUL D" 2.50%"TOXIMUL H" 2.50%"EXXON 200" 57.50%D. 1.0 Aqueous SuspensionCompound of Formula (1) 12.00%"PLURONIC P-103" 1.50%(block copolymer of propylene oxideand ethylene oxide, surfactant)"PROXEL GXL" .05%(biocide/preservative)"AF-100" .20%(silicon based antifoam agent)"REAX 88B" 1.00%(lignosulfonate dispersing agent)propylene glycol 10.00%veegum .75%xanthan .25%water 74.25%E. 1.0 Aqueous SuspensionCompound of Formula (1) 12.50%"MAKON 10" (10 moles ethyleneoxide 1.00%nonylphenol surfactant)"ZEOSYL 200" (silica) 1.00%"AF-100" 0.20%"AGRIWET FR" (surfactant) 3.00%2% xanthan hydrate 10.00%water 72.30%F. 1.0 Aqueous SuspensionCompound of Formula (1) 12.50%"MAKON 10" 1.50%"ZEOSYL 200" (silica) 1.00%"AF-100" 0.20%"POLYFON H" 0.20%(lignosulfonate dispersing agent)2% xanthan hydrate 10.00%water 74.60%G. Wettable PowderCompound of Formula (1) 25.80%"POLYFON H" 3.50%"SELLOGEN HR" 5.00%"STEPANOL ME DRY" 1.00%gum arabic 0.50%"HISIL 233" 2.50%Barden clay 61.70%H. GranulesCompound of Formula (1) 5.0%propylene glycol 5.0%Exxon 200 5.0%Florex 30/60 granular clay 85.0%______________________________________

Claims

1. A method of inhibiting a nematode population which comprises applying to the locus of a nematode, a nematode inactivating amount of a compound of the formula (1):

Het--X--CH.sub.2 --CH.sub.2 --Ar (1)

or an N-oxide or salt thereof, wherein

Het is a group selected from: ##STR3## X is O, or NH; Ar is a substituted phenyl group of formula (18), or (19). ##STR4## wherein Y is O or S;

R.sup.1 is (C.sub.2 -C.sub.5) alkyl, (C.sub.3 -C.sub.7) branched alkyl, halo (C.sub.1 -C.sub.4) alkyl, phenyl, or phenyl substituted with CF.sub.3, CN or halo;

R.sup.2 is H, F, or Cl, or R.sup.2 combines with Y--R.sup.1 to form --CH.sub.2 --CH.sub.2 --O-- or --O--CF.sub.2 --O--; and

2. A method of claim 1 wherein the compound of formula (1) being one that is able to provide at least 80% control when tested in the peanut root knot nematode assay at 12 ppm.

3. A method of claim 2 wherein the compound of formula (1) is one that is able to provide at least 80%. control when tested in the peanut root know nematode assay at 6 ppm.

4. A method of claim 1 wherein the Ar group is a substituted phenyl group of formula (18) wherein R.sup.1 is halo (C.sub.1 -C.sub.4) alkyl.

5. A method of claim 4 wherein R.sup.1 is selected from CF.sub.3, CHF.sub.2, CF.sub.2 CF.sub.3, CH.sub.2 CF.sub.3, CF.sub.2 CHF.sub.2, CH(CH.sub.3)CF.sub.3, CH.sub.2 CF.sub.2 CF.sub.2 H, and CH.sub.2 CF.sub.2 CF.sub.3.

6. A method of claim 1 wherein the Ar group is a substituted phenyl group of formula (18) wherein R.sup.1 is a (C.sub.3 -C.sub.6) branched alkyl group.

7. A method of claim 1 wherein the Ar group is a substituted phenyl group of formula (18) wherein R.sup.1 is a phenyl group that is monosubstituted with one halo or CF.sub.3 group.

8. A method of claim 1 wherein the Ar group is a substituted phenyl group of formula (18) wherein R.sup.1 is (C.sub.2 -C.sub.5) alkyl.

9. A method of claim 1 wherein the compound of formula (1) is one where the Het group is of formula (2), (3), (4), or (5).

10. A method of claim 10 wherein the Ar group is a substituted phenyl group of formula (16) wherein R.sup.1 is halo (C.sub.1 -C.sub.4) alkyl.

11. A method of claim 11 wherein R.sup.1 is fluoro (C.sub.1 -C.sub.4) alkyl.

12. A method of claim 11 wherein R.sup.1 is selected from CF.sub.3, CHF.sub.2, CF.sub.2 CF.sub.3, CH.sub.2 CF.sub.3, CF.sub.2 CHF.sub.2, CH(CH.sub.3)CF.sub.3, CH.sub.2 CF.sub.2 CF.sub.2 H, and CH.sub.2 CF.sub.2 CF.sub.3.

13. A method of claim 10 wherein the Ar group is a substituted phenyl group of formula (16) wherein R.sup.1 is a (C.sub.3 -C.sub.6) branched alkyl group.

14. A method of claim 9 wherein the Ar group is a substituted phenyl group of formula (18) wherein R.sup.1 is a phenyl group that is monosubstituted with one halo or CF.sub.3 group.

15. A method of claim 9 wherein the Ar group is a substituted phenyl group of formula (18) wherein R.sup.1 is a (C.sub.2 -C.sub.5) alkyl.

16. A method of claim 1 wherein the compound of formula (1) is 8-fluoro-4-[2-[4-(pentafluoroethoxy)phenyl]ethoxy]quinoline.

17. A method of claim 1 wherein the compound of formula (1) is 8-fluoro-4-[2-4-(t-butoxy)phenyl]ethoxy]quinoline.

18. A method of claim 1 wherein the compound of formula (1) is 8-fluoro-4-[2-4-(n-pentoxy)phenyl]ethoxy]quinoline.

19. A method of claim 1 wherein the compound of formula (1) is 8-fluoro-4-[2-[3-fluoro-4-(2,2,2-trifluoroethoxy)-phenyl]ethoxy]quinoline.

20. A method of claim 1 wherein the compound of formula (1) is 8-fluoro-N-[2-[4-(trifluoromethoxy)phenyl]ethyl]quinoline-4-amine.