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, wherein 
     Het is a nitrogen containing heterocycle, for example 8-fluoroquinazolin-4-yl, or quinoline-4-amine, 
     X is O, NH, or CH 2  ; and 
     Ar 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 2  ; Ar is a substituted phenyl group of formula (18), (19), or (20) ##STR2## wherein Y is O or S; 
     R 1  is (C 2  -C 5 ) alkyl, (C 3  -C 7 ) branched alkyl, halo (C 1  -C 4 ) alkyl, phenyl, or phenyl substituted with CF 3 , CN or halo; 
     R 2  is H, F, or Cl, or R 2  combines with Y--R 1  to form --CH 2  --CH 2  --O-- or --O--CF 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 &#34;halo&#34; refers to a F, Cl, Br, or I atom. 
     The term &#34;haloalkyl&#34; refers to straight chain and branched chain groups. 
     The term &#34;HPLC&#34; refers to a high pressure liquid chromatography. 
     The term &#34;inhibiting a nematode&#34; refers to a decrease in the numbers of living nematodes. 
     The term &#34;nematode-inactivating amount&#34; is used to describe the amount, which is sufficient to cause a measurable reduction in the treated nematode population. 
     The term &#34;peanut root knot nematode assay&#34; 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 1  is halo(C 1  -C 4 )alkyl; 
     g) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R 1  is selected from CF 3 , CHF 2 , CF 2  CF 3 , CH 2  CF 3 , CF 2  CHF 2 , CH(CH 3 )CF 3 , CH 2  CF 2  CF 2  H, and CH 2  CF 2  CF 3  ; 
     h) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R 1  is a (C 3  -C 6 ) branched alkyl group; 
     i) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R 1  is a phenyl group that is substituted with one or more halo or CF 3  groups; 
     j) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R 1  is (C 2  -C 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×-20×. 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                       °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 &gt;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    °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%&#34;TOXIMUL D&#34;               2.50%(nonionic/anionic surfactant blend)&#34;TOXIMUL H&#34;               2.50%(nonionic/anionic surfactant blend)&#34;EXXON 200&#34;               85.62%(naphthalenic solvent)B. 1.5 Emulsifiable ConcentrateCompound of Formula (1)   18.50%&#34;TOXIMUL D&#34;               2.50%&#34;TOXIMUL H&#34;               2.50%&#34;EXXON 200&#34;               76.50%C. 1.0 Emulsifiable ConcentrateCompound of Formula (1)   12.50%N-methylpyrrolidone       25.00%&#34;TOXIMUL D&#34;               2.50%&#34;TOXIMUL H&#34;               2.50%&#34;EXXON 200&#34;               57.50%D. 1.0 Aqueous SuspensionCompound of Formula (1)   12.00%&#34;PLURONIC P-103&#34;          1.50%(block copolymer of propylene oxideand ethylene oxide, surfactant)&#34;PROXEL GXL&#34;              .05%(biocide/preservative)&#34;AF-100&#34;                  .20%(silicon based antifoam agent)&#34;REAX 88B&#34;                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%&#34;MAKON 10&#34; (10 moles ethyleneoxide                     1.00%nonylphenol surfactant)&#34;ZEOSYL 200&#34; (silica)     1.00%&#34;AF-100&#34;                  0.20%&#34;AGRIWET FR&#34;  (surfactant)                     3.00%2% xanthan hydrate        10.00%water                     72.30%F. 1.0 Aqueous SuspensionCompound of Formula (1)   12.50%&#34;MAKON 10&#34;                1.50%&#34;ZEOSYL 200&#34; (silica)     1.00%&#34;AF-100&#34;                  0.20%&#34;POLYFON H&#34;               0.20%(lignosulfonate dispersing agent)2% xanthan hydrate        10.00%water                     74.60%G. Wettable PowderCompound of Formula (1)   25.80%&#34;POLYFON H&#34;               3.50%&#34;SELLOGEN HR&#34;             5.00%&#34;STEPANOL ME DRY&#34;         1.00%gum arabic                0.50%&#34;HISIL 233&#34;               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%______________________________________