Pyrimidine compounds as herbicides

FIELD OF THE INVENTION
This invention relates to novel substituted heterocyclic compounds and a method for controlling undesired vegetation in crops including plantation and specialty crops. Some of the compounds of the instant invention have been disclosed previously for use generally as herbicides, but these disclosures provide no teachings for use of these compounds as herbicides in plantation crops.
BACKGROUND OF THE INVENTION
U.S. Pat. No. 4,859,229 discloses herbicidal utility in "cotton and soya" cultivations for compounds of the formula ##STR2## wherein, inter alia R.sup.1 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, formyl or C.sub.2 -C.sub.6 alkanoyl;
R.sup.2 is (in part) an ether group;
R.sup.3 is H or CN;
R.sup.4 is H or halogen;
R.sup.5 is H, halogen or C.sub.1 -C.sub.4 alkyl;
R.sup.6 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl; and
R.sup.5 and R.sup.6 together are tri- or tetramethylene.
The instant invention provides a method for controlling undesired vegetation in plantation and specialty crops. Many of the compounds of the instant invention have been previously disclosed for use generally as herbicides, and such disclosures are found in U.S. Pat. No. 4,859,229, EP-A-438,209, JP 3-77,874 and EP-A-408,382. There are, however, no teachings for the use of these compounds as herbicides in plantation and specialty crops such as citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, plantain, pineapple, fruit trees such as apples, and nut trees. These crops are important markets and are cultivated particularly in regions of the Pacific rim and South America. Citrus, sugarcane and loblolly pine also are grown elsewhere.
The yields of selected crops such as citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, fruit trees and Bermudagrass tend to be lessened by undesired plantings such as crabgrass, johnson grass, guineagrass and the like. In addition, the yields of these crops tend to be reduced by crop plants such as corn, cotton, wheat, rice, and the like. A need therefore exists for controlling these types of plantings to improve the yields of selected crops such as those mentioned above.
This invention also provides novel substituted heterocyclic compounds and their agriculturally suitable compositions which are generally useful as herbicides, as well as methods of their use as general or selective preemergent or postemergent herbicides, or as plant growth regulants.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as sugarcane, citrus, oil palm, cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
SUMMARY OF THE INVENTION
This invention comprises a method for controlling the growth of undesired vegetation in a plantation crop by applying to the locus of the crop an effective amount of a compound of Formula I ##STR3## A is O or S; R.sup.1 is C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogen, OR.sup.5, SR.sup.6 or CN; C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl, each optionally substituted with 1-3 halogen; formyl; or C.sub.2 -C.sub.6 alkanoyl;
R.sup.2 is H, isopropyl, allyl, propargyl, CH(CH.sub.3)C.ident.CH, benzyl, CHR.sup.7 CO.sub.2 R.sup.8 or may be taken together with Z;
R.sup.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or N(CH.sub.3).sub.2 ;
R.sup.4 is H or halogen;
R.sup.3 and R.sup.4 may be taken together as --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --;
R.sup.5 and R.sup.6 are independently H or C.sub.1 -C.sub.3 alkyl;
R.sup.7 and R.sup.8 are independently C.sub.1 -C.sub.2 alkyl;
X is Cl or Br;
Y is F or Cl;
Z is H or may be taken together with R.sup.2 as ##STR4## such that the linking A atom is attached to the methine carbon; R.sup.9 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, cyclopropyl, vinyl, C.sub.2 alkynyl, CN, C(O)R.sup.10, CO.sub.2 R.sup.10, CONR.sup.10 R.sup.11, CR.sup.12 R.sup.13 C(O)R.sup.10, CR.sup.12 R.sup.13 CO.sub.2 R.sup.10, CR.sup.12 R.sup.13 CONR.sup.10 R.sup.11, CHR.sup.12 OH, CHR.sup.12 OC(O)R.sup.10 or CHR.sup.12 OC(O)NR.sup.10 R.sup.11 ; and
R.sup.10, R.sup.11, R.sup.12 and R.sup.13 are independently H or C.sub.1 -C.sub.3 alkyl.
Preferred for reasons including greater herbicidal efficacy are:
1) The method wherein for Compounds of Formula I
R.sup.1 is C.sub.1 -C.sub.3 alkyl optionally substituted with 1 to 3 F atoms or Cl atoms, O(C.sub.1 -C.sub.2 alkyl), S (C.sub.1 -C.sub.2 alkyl) or CN; C.sub.3 -C.sub.4 alkenyl optionally substituted with 1 to 3 F atoms or Cl atoms; C.sub.3 -C.sub.4 alkynyl; or C.sub.2 -C.sub.3 alkanoyl;
R.sup.2 is H, isopropyl, allyl, propargyl, CH(CH.sub.3)C.ident.CH, CHR.sup.7 CO.sub.2 R.sup.8 or may be taken together with Z;
R.sup.3 is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl or N(CH.sub.3).sub.2 ;
R.sup.4 is H, F, Cl or Br;
R.sup.3 and R.sup.4 may be taken together as --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --; and
X is Cl.
2) The method of Preferred 1 wherein
R.sup.1 is CH.sub.3 optionally substituted with 1 to 3 F atoms or Cl atoms; CH.sub.2 CN; allyl; or propargyl;
R.sup.3 is CF.sub.3 ; and
R.sup.4 is H.
3) The method of Preferred 2 wherein
R.sup.9 is CH.sub.3 ;
A is O; and
Q is Q-1.
Specifically Preferred for reasons of greatest herbicidal efficacy are the method of Preferred 3 which are the use of the compounds:
3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;
3-[4-chloro-2-fluoro-5-(2-propenyloxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;
3-(5,7-dichloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione; and
3-(7-choro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;
and the method of Preferred 2 which is the use of the compound:
3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-6-dimethylamino-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione.
This invention also comprises compounds of Formulas II and III, agriculturally suitable compositions containing them, and their use as preemergent and/or postemergent herbicides. ##STR5## wherein A is O or S;
R.sup.1 is C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogen, OR.sup.5, SR.sup.6 or CN; C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl, each optionally substituted with 1-3 halogens; formyl; or C.sub.2 -C.sub.6 alkanoyl;
R.sup.2 is H, isopropyl, allyl, propargyl, CH(CH.sub.3)C.ident.CH, benzyl, CHR.sup.7 CO.sub.2 R.sup.8 or may be taken together with Z;
R.sup.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or N(CH.sub.3).sub.2 ;
R.sup.4 is H or halogen;
R.sup.3 and R.sup.4 may be taken together as --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --;
R.sup.5 and R.sup.6 are independently H or C.sub.1 -C.sub.3 alkyl;
R.sup.7 and R.sup.8 are independently C.sub.1 -C.sub.2 alkyl;
X is Cl or Br;
Y is F or Cl;
Z is H or may be taken together with R.sup.2 as ##STR6##
such that the linking A atom is attached to the methine carbon; and
R.sup.9 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, cyclopropyl, vinyl, C.sub.2 alkynyl, CN, C(O)R.sup.10, CO.sub.2 R.sup.10, CONR.sup.10 R.sup.11, CR.sup.12 R.sup.13 C(O)R.sup.10, CR.sup.12 R.sup.13 CO.sub.2 R.sup.10, CR.sup.12 R.sup.13 CONR.sup.10 R.sup.11, CHR.sup.12 OH, CHR.sup.12 OC(O)R.sup.10 or CHR.sup.12 OC(O) NR.sup.10 R.sup.11 ; and
R.sup.10, R.sup.11, R.sup.12 and R.sup.13 are independently H or C.sub.1 -C.sub.3 alkyl;
provided that
1) in compounds of Formula II, when R.sup.1 is C.sub.1 -C.sub.4 alkyl optionally substituted with halogen, OR.sup.5 or CN; C.sub.3 -C.sub.4 alkenyl; formyl; or C.sub.2 -C.sub.6 alkanoyl; R.sup.3 is C.sub.1 -C.sub.4 haloalkyl; and R.sup.5 is C.sub.1 -C.sub.3 alkyl; then R.sup.2 is benzyl or taken together with Z;
2) in compounds of Formula II, when R.sup.1 is CH.sub.2 OH or C.sub.1 -C.sub.3 alkyl optionally substituted with halogen; R.sup.3 is C.sub.1 -C.sub.4 haloalkyl; and A is S; then R.sup.2 is taken together with Z;
3) in compounds of Formula III, when R.sup.1 is C.sub.1 -C.sub.4 alkyl and R.sup.3 is CH.sub.3 or CF.sub.3 then R.sup.2 is benzyl or taken together with Z;
4) in compounds of Formula II, when R.sup.1 is C.sub.1 -C.sub.4 alkyl optionally substituted with halogen; formyl; or C.sub.2 -C.sub.6 alkanoyl; then R.sup.2 is taken together with Z.
Preferred for reasons including ease of synthesis and/or greater herbicidal efficacy are:
1) Compounds of Formulas II and III wherein
R.sup.1 is C.sub.1 -C.sub.3 alkyl optionally substituted with 1 to 3 F atoms or Cl atoms, O(C.sub.1 -C.sub.2 alkyl), S(C.sub.1 -C.sub.2 alkyl) or CN; C.sub.3 -C.sub.4 alkenyl optionally substituted with 1 to 3 F atoms or Cl atoms; C.sub.3 -C.sub.4 alkynyl; or C.sub.2 -C.sub.3 alkanoyl;
R.sup.2 is H, isopropyl, allyl, propargyl, CH(CH.sub.3)C.ident.CH, CHR.sup.7 CO.sub.2 R.sup.8 or may be taken together with Z;
R.sup.3 is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl or N(CH.sub.3).sub.2 ;
R.sup.4 is H, F, Cl or Br;
R.sup.3 and R.sup.4 may be taken together as --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --; and
X is Cl.
2) Compounds of Preferred 1 wherein
R.sup.1 is CH.sub.3 optionally substituted with 1 to 3 F atoms or Cl atoms; CH.sub.2 CN; allyl; or propargyl;
R.sup.3 is CF.sub.3 ; and
R.sub.4 is H.
3) Compounds of Preferred 2 wherein the compound is of Formula II;
R.sup.9 is CH.sub.3 ; and
A is O.
Specifically Preferred for reasons of ease of synthesis and/or greatest herbicidal efficacy are the compound of Preferred 2 which is:
3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-6-(dimethylamino-1-methyl-1,3,5-triazine-2,4(1H,3H) -dione;
and the compounds of Preferred 3 which are
3-(5,7-dichloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione; and
3-(7-choro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione.
In the above definitions, the term "alkyl", used either alone or in compound words such as "haloalkyl", includes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers. Alkenyl includes straight chain or branched alkenes, e.g., 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers. The term "halogen", either alone or in compound words such as "haloalkyl", means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH.sub.2 CH.sub.2 F, CF.sub.2 CF.sub.3 and CH.sub.2 CHFCl.
DETAILED DESCRIPTION OF THE INVENTION
Many of the compounds of Formula I wherein Z and R.sup.2 are not taken together can be prepared according to the procedures of U.S. Pat. No. 4,859,229 and U.S. Pat. No. 3,902,887, the disclosures of which are herein incorporated by reference.
Schemes 1 to 4 illustrate the preparation of compounds of Formula II wherein Z and R.sup.2 are taken together. ##STR7##
The dihydrofuran ring of compounds of Formula II can be prepared according to the procedure of U.S. Pat. No. 4,881,967 by Claisen rearrangement of allyl ether VII followed by cyclization as shown in Scheme 1, Equations (c) and (d). The rearrangement and cyclization normally require high temperatures ranging from 100.degree. C. to 200.degree. C. Therefore, it is preferable to perform this process at an early stage with an inert protecting group on nitrogen. For this reason, phthalimide VII is prepared via treatment of hydroxyaniline V with phthalic anhydride IV followed by allylation of the hydroxy group of VI in the presence of a weak base such as potassium carbonate (Scheme 1, Equations (a) and (b)).
Alternatively, the compound VII can be prepared by allylation of V first followed by treatment with phthalic anhydride IV.
The rearrangement of VII can be effected by heating in an inert solvent such as N,N-dimethylaniline or o-dichlorobenzene at a temperature of about 100.degree. C. to 200.degree. C. This Claisen rearrangement can also proceed with titanium tetrachloride and N-trimethylsilylacetanilide at ambient temperature in an inert solvent such as dichloromethane (Narasaka, K., Bald E., and Mukaiyama T.; Chemistry Letters 1975, 1041). The cyclization of VIII to give IXa can be effected by refluxing a solution of phenol VIII in an inert solvent, such as xylene, containing a catalytic to stoichiometric amount of acid such as p-toluenesulfonic acid under Dean-Stark apparatus at a temperature range of from about 120.degree. C. to 180.degree. C. (Scheme 1, Equation (d)). ##STR8##
For the preparation of dihydrothiophene IXb, the allylphenol VIII is treated with N,N-dimethylthiocarbamoyl chloride in the presence of a weak base such as potassium carbonate in an inert solvent such as acetone or N,N-dimethylformamide at a temperature between 0.degree. C. and refluxing temperatures of the solvents over several hours as shown in Scheme 2a, Equation (a).
Thermal rearrangement of X may be effected in a suitable inert solvent such as o-dichlorobenzene at 150.degree.-250.degree. C. to produce carbamate derivative XI. Cyclization of XI with an anhydrous acid such as hydrogen bromide in acetic acid at refluxing temperatures affords IXb as shown in Scheme 2a, Equation (c).
The acetylene substituted dihydrofuran ring of compounds of Formulas II and III (i.e., R.sup.9 is C.sub.2 alkynyl) can be prepared as shown in Scheme 2b. ##STR9##
The hydroxyl group of VIII of Scheme 1, Equation (c) can be protected by a silicon protecting group using reagents such as trimethylsilyl chloride or t-butyldimethylsilyl chloride to give XXXIV. Then the reductive ozonolysis of XXXIV gives aldehyde XXXV. The diol XXXVI can be prepared by the treatment of aldehyde XXXV with lithium salt of trimethylsilylacetylene. The deprotections of both silyl protecting groups of XXXVI can be accomplished using fluoride ions such as potassium fluoride. The acetylenic hydrofuran XXXVIII can be prepared from the diol XXXVII by Mitsunobu condition using diethyl azodicarboxylate (DEAD) and triphenylphosphine according to the known procedure (Macor, J., Ryan, K., and Newman, M.; Tetrahedron 1992, 48, 1039).
The vinyl group substituted dihydrofuran ring of compounds of Formula II and III can be prepared as shown in Scheme 2c. ##STR10##
The hydroxymethyl hydrofuran XXXIX can be prepared by treatment of VIII with m-chloroperbenzoic acid (MCPBA) followed by p-toluenesulfonic acid. The treatment of XXXIX with carbon tetrabromide and triphenylphosphine gives bromomethyl hydrofuran XL. The Wittig reagent XLI can be prepared by the treatment of XL with triphenylghosphine in an inert solvent such as DMF. The vinylic hydrofuran XLII can be prepared by Wittig reaction of XLI and formaldehyde.
The hydroxy group of XXXIX can be converted to ketone, carboxylic acid, ester or amide groups by methods well known to those skilled in the art. This transformation can be carried out before or after the phthalimide protecting group is removed. If the protecting group is removed first, then the unprotected aniline derivative is first converted to the uracil or triazinedione ring (as described later) before further conversion of the hydroxyl group. ##STR11##
The phthalimide protecting group of IXa or IXb can be removed by hydrazine at ambient temperature to afford aniline XII. The formation of isocyanate XIII is accomplished by treatment of the aniline XII with phosgene or triphosgene in the presence of a base such as triethylamine at ambient temperature, or without base in an inert solvent such as dioxane or toluene at a temperature range of from 60.degree. C. to 120.degree. C. (Scheme 3). ##STR12##
The formation of the uracil ring in compound XV is carried out by the procedure described in U.S. Pat. No. 4,943,309. A suitable salt of an enamine XIV is treated with the isocyanate XIII at low temperature over several hours, typically between -50.degree. C. and -70.degree. C. in an inert solvent such as toluene, and the reaction is continued at ambient temperature for several hours. The alkylation of XV can be accomplished by treatment of XV with C.sub.1-4 alkyl halide, or C.sub.1-4 haloalkyl halide, especially the respective chloride or bromide, or sulphate in the presence of a base such as potassium carbonate or sodium hydride in an inert solvent such as acetone or acetonitrile at a temperature range of from about 0.degree. C. to 120.degree. C. The acylation of XV is carried out with acetic anhydride or a C.sub.2-6 alkanecarboxylic acid halide, in the presence of base such as sodium hydride.
Schemes 5 and 6 illustrate the preparation of compounds of Formula III. ##STR13##
The formation of the triazinedione ring follows the procedure described in U.S. Pat. No. 3,902,887 when R.sup.3 is a dimethylamino group as shown in Scheme 5. N-Ethoxycarbonylguanidine XVI is mixed with an isocyanate XVII in an inert solvent, preferably toluene, while the temperature is maintained at 25.degree. C. to 100.degree. C., preferably 55.degree. C. to 80.degree. C. The mixture of slurry containing compound XVIII is cooled, if necessary, to 24.degree. C.-45.degree. C., while dimethylamine is added, either as a gas or a liquid. It is preferred to add the amine at 25.degree. C.-35.degree. C., and it is important to have at least 1.0 molar equivalent and preferably, 1.0 to 2.5 molar equivalents of dimethylamine. Next a ring closure catalyst is added. The catalyst is an alkali metal alkoxide (or hydroxide) and it may be added either as a dry solid or as a solution in the alkanol. Dry sodium methoxide or a solution of sodium methoxide in methanol is a preferred catalyst. The amount of catalyst needed is from 0.1 to 5.0 mole percent of compound XVIII. The ring closure reaction can proceed at a temperature between 0.degree. C. and 120.degree. C. The reaction is rapid and normally complete in less than several hours. ##STR14##
When R.sup.3 is C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 haloalkyl substituents, the formation of the triazinedione ring follows the procedure described by JP 03 77,874 as shown in Scheme 6. Carbamoylation of alkylamidine hydrochloride or haloalkylamidine hydrochloride XIX with isocyanate XVII under the condition described in Scheme 5 or in the presence of NaOH in aqueous acetone gives N-phenylcarbamoyl amidine XX. The cyclocondensation of the resulting compound XX with ethyl chloroformate in the presence of base such as sodium hydride or sodium methoxide in an inert solvent such as tetrahydrofuran gives triazinedione XXII via XXI. The alkylation of XXII can be accomplished by treatment of XXII with C.sub.1-4 alkyl halide, or C.sub.1 -C.sub.4 haloalkyl halide, especially the respective chloride, bromide or sulphate in the presence of a base such as potassium carbonate or sodium hydride in an inert solvent such as acetone or acetonitrile at a temperature range of from about 0.degree. C. to 120.degree. C. The acylation of XXII is carried out with acetic anhydride or a C.sub.2 -C.sub.6 alkanecarboxylic acid halide in the presence of base such as sodium hydride. ##STR15##
Compounds of Formula II wherein Z is hydrogen and A is oxygen can be prepared according to Scheme 7. Cyclocondensation of enamine XIV can be carried out with benzyl ether protected isocyanate XXIII. The enamine XIV wherein R.sup.3 and R.sup.4 are taken together as --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- can be prepared according to the known procedure (Kloek, J., and Leschinsky, K.; J. Org Chem., 1978, 43, 1460). Other enamines of Formula XIV wherein R.sup.3 and R.sup.4 are not taken together can be prepared by one skilled in the art. The resultant uracil XXIV is alkylated or acylated as described previously and benzyl ether XXV can be deprotected easily with 5 to 10% palladium on charcoal under hydrogen pressure ranging from 20 to 50 psi. The resulting phenol XXVI is treated with C.sub.1 -C.sub.4 alkyl halide, or C.sub.1 -C.sub.4 haloalkyl halide, especially the respective chloride or bromide in the presence of a base such as potassium carbonate or sodium hydride in an inert solvent such as acetone or acetonitrile at a temperature range of from about 0.degree. C. to 120.degree. C. to give XXVII. ##STR16##
The compound XXX which has two identical R.sup.10 substituents (wherein R.sup.10 is isopropyl, allyl or C.sub.3 -C.sub.4 alkynyl) can be prepared by deprotection of benzyl ether XXIV with palladium on charcoal under hydrogen followed by alkylation or acylation in the presence of base as shown in Scheme 8. ##STR17##
The same procedure can be adopted for the synthesis of triazinediones of Formula III wherein Z is hydrogen and A is oxygen as shown in Scheme 9. The cyclocondensation product XXXI from N-ethoxycarbonylguanidine XVI and benzyl ether protected isocyanate XXIII is treated with palladium on charcoal under hydrogen pressure ranging from 20 to 50 psi followed by alkylation or acylation in the presence of base to give XXXIII.

EXAMPLE 1
Preparation of 3-[4-chloro-2-fluoro-5-[(2-propynyl)-oxy]phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H, 3H)-pyrimidinedione
To a solution of 200 mg (0.59 mmol) of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-1-methyl-6- (trifluoromethyl)-2,4 (1H,3H) -pyrimidinedione in 3 mL of acetonitrile was added 162 mg of potassium carbonate (1.18 mmol) and 131 mL (1.18 mmol) of an 80% solution of propargyl bromide in toluene. It was warmed under reflux for 2 h. The resulting mixture was filtered and the filtrate was concentrated in vacuo to give colorless oil which was flash chromatographed over silica gel, eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 204 mg of title compound as a white foam: .sup.1 H-NMR (CDCl.sub.3, 200 MHz) ppm 7.35 (d, 1H), 7.0 (d, 1H), 6.4 (s, 1H), 4.78 (d, 2H), 3.58 (s, 3H), 2.6 (d, 1H).
EXAMPLE 2
Preparation of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H, 3H) -pyrimidinedione
A mixture of 1.12 g (2.61 mmol) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione and 220 mg of 10% palladium on charcoal in 40 mL of ethyl acetate was placed in a Paar bottle and was agitated under 45 psi hydrogen over a 20 hour period. It was filtered and washed with 100 mL of ethyl acetate. The filtrate was concentrated in vacuo and the resultant crude product flash chromatographed over silica gel eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 521 mg of the title compound as a white foam.: .sup.1 H-NMR (CDCl.sub.3, 200 MHz) ppm 7.15 (d, 1H) , 6.9 (d, 1H) , 6.4 (s, 1H), 5.8 (s, 1H), 3.6 (s, 3H).
EXAMPLE 3
Preparation of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
A mixture of 1.85 g (4.46 mmol) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-6-(trifluoromethyl)-2,4(1H, 3H)-pyrimidinedione, 492 .mu.L (5.20 mmol) of dimethylsulfate, and 749 mg (8.92 mmol) of sodium bicarbonate in 20 mL of acetone was warmed under reflux for 3 h. Evaporation removed the solvent to give a viscous residue. It was dissolved in 50 mL of ether and washed twice with 30 mL of water, dried (MgSO.sub.4) and concentrated in vacuo to give white solid which was flash chromatographed over silica gel, eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 1.19 g of the title compound as a white solid, m.p.: 145.degree.-147.degree. C.; .sup.1 H-NMR (CDCl.sub.3, 200 MHz) ppm 7.4 (m, 6H), 6.85 (d, 1H), 6.4 (s, 1H), 5.1 (s, 2H), 3.55 (s, 3H).
EXAMPLE 4
Preparation of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)-phenyl]-6-(trifluoromethyl)-2,4(1H,3H) -pyrimidinedione
To a solution of 312 mg (7.82 mmol) of sodium hydride (60% oil dispersion) in 10 mL of N,N-dimethylformamide was added 1.43 g (7.82 mmol) of ethyl-3-amino-4,4,4-trifluorocrotonate in 7 mL of toluene over a period of 30 min at -5.degree. C. The resulting mixture was stirred for an additional 30 min before it was cooled to -70.degree. C. Then a solution of 2.17 g (7.82 mmol) of 4-chloro-2-fluoro-5-(phenylmethoxy)phenyl isocyanate in 7 mL of toluene was added dropwise at a rate that maintained the reaction temperature below -60.degree. C. After the addition, the thick reaction mixture was maintained at -60.degree. C. for an additional 1 h before the cooling bath was removed. The mixture was gradually warmed to room temperature and stirring was continued for 1.5 h. Then the mixture was poured into a solution of 10 mL of concentrated HCl in 200 mL of water. The toluene layer was separated and the aqueous layer was further extracted twice with 200 mL of ether, dried (MgSO.sub.4), concentrated in vacuo to give yellow oil which was flash chromatographed over silica gel eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 1.85 g of the title compound as a pale yellow foam: .sup.1 H-NMR (CDCl.sub.3, 200 MHz): ppm 7.40 (m, 6H), 6.85 (d, 1H), 6.2 (s, 1H), 5.05 (s, 2H).
EXAMPLE 5
Preparation of 3-[4-chloro-2-fluoro-5-[(2-propynyl)-oxy]phenyl]-1-(2-propynyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
To a stirred solution of 500 mg (1.50 mmol) of 3-[4 -chloro-2-fluoro-5-(hydroxy)phenyl]-6-trifluoromethyl-2,4(1H,3H) -pyrimidinedione in 20 mL of acetonitrile was added 425 mg (3.1 mmol) of potassium carbonate and 0.34 mL (3.10 mmol) of 80% solution of propargyl bromide in toluene. The stirred mixture was then refluxed gently under nitrogen for 2 h. The solution was filtered, washed with ethyl acetate, and concentrated in vacuo. The resulting yellow oil was flash chromatographed over silica gel, eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 90 mg of the title compound as a pale yellow oil: .sup.1 H-NMR (CDCl.sub.3, 200 MHz): ppm 7.35 (d, 1H), 7.0 (d, 1H), 6.4 (s, 1H), 4.75 (m, 4H), 2.6 (m, 1H), 2.4 (m, 1H). It also gives 150 mg of 3-[4-chloro-2-fluoro-5-[(2-propynyl) oxy]phenyl]-1-6-(trifluoromethyl)-2,4 (1H,3H)-pyrimidinedione as a yellow oil: .sup.1 H-NMR (DMSO-d.sub.6): ppm 7.7 (d, 1 H), 7.4 (d, 1H), 6.4 (s, 1H), 4.8 (d, 2H), 2.5 (m, 1H).
EXAMPLE 6
Preparation of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione
A mixture of 4.27 g (10.3 mmol) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione and 420 mg of 10% palladium on charcoal in 70 mL of ethyl acetate was placed in a Paar bottle and was agitated under 45 psi hydrogen over a 16 hour period. It was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo and the resultant crude product flash chromatographed over silica gel, eluting with a 95:5 v:v mixture of dichloromethane and methanol to give 2.50 g of the title compound as a pale orange solid, m.p.: 68.degree.-72.degree. C.; .sup.1 H-NMR (DMSO-d.sub.6): ppm 7.5 (d, 1H), 7.0 (d, 1H), 6.4 (s, 1H).
EXAMPLE 7
Preparation of 3-[4-chloro-2-fluoro-5-[(2-propynyl)-oxy]phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione
To a solution of 2.80 g (8.90 mmol) of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H) -dione in 50 mL of acetone was added 1.47 g (10.7 mmol) of potassium carbonate and 1.98 mL (17.8 mmol) of an 80% solution of propargyl bromide in toluene. It was then warmed to reflux for 2 h. It was cooled to room temperature and the mixture was filtered and washed with excess ethyl acetate. The crude product was flash chromatographed over silica gel, eluting with a 3:7 v:v mixture of ethyl acetate and hexane to give 3.1 g of the title compound as a pale yellow solid, m.p.: 61.degree.-65.degree. C.; .sup.1 H-NMR (CDCl.sub.3, 200 MHz) ppm 7.0 (d, 1H), 4.75 (m, 2H), 3.45 (s, 3H), 3.1 (s, 6H), 2.6 (m, 1H).
EXAMPLE 8
Preparation of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione
A mixture of 4.62 g (11.4 mmol) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione and 460 mg of 10% palladium on charcoal in 50 mL of ethyl acetate was placed in a Paar bottle and was agitated under 45 psi hydrogen over a 14 hour period. It was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo and the resultant crude product flash chromatographed over silica gel eluting with a 1:1 v:v mixture of ethyl acetate and hexane to give 3.2 g of the title compound as a pale grey solid, m.p.: 247.degree.-249.degree. C. (dec); .sup.1 H-NMR (DMSO-d.sub.6) ppm 7.45 (d, 1H), 6.95 (d, 1H), 3.3 (s, 3H), 3.0 (s, 6H).
EXAMPLE 9
Preparation of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)-phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione
To a solution of 5.05 g (29.2 mmol) of N-ethoxycarbonyl-N,N', N"-trimethylguanidine in 25 mL of toluene was added a solution of 7.72 g (27.8 mmol) of 4-chloro-2-fluoro-5-(phenylmethoxy)phenyl isocyanate in 50 mL of toluene over a period of 30 min while maintaining the temperature between 55.degree. C. and 80.degree. C. It was then stirred at the same temperature for an hour. To a solution of the resulting N-[N-[4-chloro-2-fluoro-5-(phenylmethoxy) phenyl]carbamoyl-N',N'-dimethylamidino]-N-methylcarbamate in toluene was added 3.21 g (71.5 mmol) of dimethylamine in 10 mL of toluene at room temperature. While the temperature was between 25.degree. C. and 40.degree. C., 45 mg (0.834 mmol) of sodium methoxide was added. After 30 min, it was quenched with 100 mL of water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with 0.1N hydrochloric acid, brine, and water, dried (MgSO.sub.4) and concentrated in vacuo. The crude product was flash chromatographed over silica gel eluting with a 1:1 v:v mixture of ethyl acetate and hexane to give 5.3 g of the title compound as a brown solid, m.p.: 193.degree.-194.degree. C.; .sup.1 H-NMR (CDCl.sub.3, 200 MHZ) ppm 7.4 (m, 6H), 6.95 (d, 1H), 5.05 (d, 2H), 3.45 (s, 3H), 3.1 (s, 6H).
Using the procedures outlined in Schemes 1-9, and Examples 1-9, the compounds of this invention including the compounds of Tables I-III can readily be prepared by one skilled in the art.
TABLE I______________________________________ ##STR18##R.sup.1 R.sup.2 R.sup.3 R.sup.4 A X Y______________________________________CH.sub.3 H CF.sub.3 H O Cl FCH.sub.3 H CF.sub.3 H S Cl FCH.sub.3 H CF.sub.3 H O Cl ClCH.sub.3 H CF.sub.3 H S Cl ClCH.sub.3 H CF.sub.3 Br O Cl FCH.sub.3 H CF.sub.3 Br S Cl FCH.sub.3 H CF.sub.3 Br O Cl ClCH.sub.3 H CF.sub.3 Br S Cl ClCH.sub.3 CH.sub.2 Ph CF.sub.3 H O Cl FCH.sub.3 CH.sub.2 Ph CF.sub.3 H S Cl FCH.sub.3 CH.sub.2 Ph CF.sub.3 H O Cl ClCH.sub.3 CH.sub.2 Ph CF.sub.3 H S Cl ClCH.sub.3 CH.sub.2 Ph CF.sub.3 Br O Cl FCH.sub.3 CH.sub.2 Ph CF.sub.3 Br S Cl FCH.sub.3 CH.sub.2 Ph CF.sub.3 Br O Cl ClCH.sub.3 CH.sub.2 Ph CF.sub.3 Br S Cl ClCH.sub.3 ##STR19## CF.sub.3 H O Cl FCH.sub.3 ##STR20## CF.sub.3 H S Cl FCH.sub.3 ##STR21## CF.sub.3 H O Cl ClCH.sub.3 ##STR22## CF.sub.3 H S Cl ClCH.sub.3 ##STR23## CF.sub.3 Br O Cl FCH.sub.3 ##STR24## CF.sub.3 Br S Cl FCH.sub.3 ##STR25## CF.sub.3 Br O Cl ClCH.sub.3 ##STR26## CF.sub.3 Br S Cl ClCH.sub.3 iPr CF.sub.3 H O Cl FCH.sub.3 iPr CF.sub.3 H S Cl FCH.sub.3 iPr CF.sub.3 H O Cl ClCH.sub.3 iPr CF.sub.3 H S Cl ClCH.sub.3 iPr CF.sub.3 Br O Cl FCH.sub.3 iPr CF.sub.3 Br S Cl FCH.sub.3 iPr CF.sub.3 Br O Cl ClCH.sub.3 iPr CF.sub.3 Br S Cl ClCH.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 H O Cl FCH.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 H S Cl FCH.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 H O Cl ClCH.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 H S Cl ClCH.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 Br O Cl FCH.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 Br S Cl FCH.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 Br O Cl ClCH.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 Br S Cl ClCF.sub.3 H CF.sub.3 H O Cl FCF.sub.3 H CF.sub.3 H S Cl FCF.sub.3 H CF.sub.3 H O Cl ClCF.sub.3 H CF.sub.3 H S Cl ClCF.sub.3 H CF.sub.3 Br O Cl FCF.sub.3 H CF.sub.3 Br S Cl FCF.sub.3 H CF.sub.3 Br O Cl ClCF.sub.3 H CF.sub.3 Br S Cl ClCF.sub.3 CH.sub.2 Ph CF.sub.3 H O Cl FCF.sub.3 CH.sub.2 Ph CF.sub.3 H S Cl FCF.sub.3 CH.sub.2 Ph CF.sub.3 H O Cl ClCF.sub.3 CH.sub.2 Ph CF.sub.3 H S Cl ClCF.sub.3 CH.sub.2 Ph CF.sub.3 Br O Cl FCF.sub.3 CH.sub.2 Ph CF.sub.3 Br S Cl FCF.sub.3 CH.sub.2 Ph CF.sub.3 Br O Cl ClCF.sub.3 CH.sub.2 Ph CF.sub.3 Br S Cl ClCF.sub.3 ##STR27## CF.sub.3 H O Cl FCF.sub.3 ##STR28## CF.sub.3 H S Cl FCF.sub.3 ##STR29## CF.sub.3 H O Cl ClCF.sub.3 ##STR30## CF.sub.3 H S Cl ClCF.sub.3 ##STR31## CF.sub.3 Br O Cl FCF.sub.3 ##STR32## CF.sub.3 Br S Cl FCF.sub.3 ##STR33## CF.sub.3 Br O Cl ClCF.sub.3 ##STR34## CF.sub.3 Br S Cl ClCF.sub.3 iPr CF.sub.3 H O Cl FCF.sub.3 iPr CF.sub.3 H S Cl FCF.sub.3 iPr CF.sub.3 H O Cl ClCF.sub.3 iPr CF.sub.3 H S Cl ClCF.sub.3 iPr CF.sub.3 Br O Cl FCF.sub.3 iPr CF.sub.3 Br S Cl FCF.sub.3 iPr CF.sub.3 Br O Cl ClCF.sub.3 iPr CF.sub.3 Br S Cl ClCF.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 H O Cl FCF.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 H S Cl FCF.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 H O Cl ClCF.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 H S Cl ClCF.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 Br O Cl FCF.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 Br S Cl FCF.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 Br O Cl ClCF.sub.3 CH.sub.2 CCH.sub.2 CF.sub.3 Br S Cl Cl ##STR35## H CF.sub.3 H O Cl F ##STR36## H CF.sub.3 H S Cl F ##STR37## H CF.sub.3 H O Cl Cl ##STR38## H CF.sub.3 H S Cl Cl ##STR39## H CF.sub.3 Br O Cl F ##STR40## H CF.sub.3 Br S Cl F ##STR41## H CF.sub.3 Br O Cl Cl ##STR42## H CF.sub.3 Br S Cl Cl ##STR43## CH.sub.2 Ph CF.sub.3 H O Cl F ##STR44## CH.sub.2 Ph CF.sub.3 H S Cl F ##STR45## CH.sub.2 Ph CF.sub.3 H O Cl Cl ##STR46## CH.sub.2 Ph CF.sub.3 H S Cl Cl ##STR47## CH.sub.2 Ph CF.sub.3 Br O Cl F ##STR48## CH.sub.2 Ph CF.sub.3 Br S Cl F ##STR49## CH.sub.2 Ph CF.sub.3 Br O Cl Cl ##STR50## CH.sub.2 Ph CF.sub.3 Br S Cl Cl ##STR51## ##STR52## CF.sub.3 H O Cl F ##STR53## ##STR54## CF.sub.3 H S Cl F ##STR55## ##STR56## CF.sub.3 H O Cl Cl ##STR57## ##STR58## CF.sub.3 H S Cl Cl ##STR59## ##STR60## CF.sub.3 Br O Cl F ##STR61## ##STR62## CF.sub.3 Br S Cl F ##STR63## ##STR64## CF.sub.3 Br O Cl Cl ##STR65## ##STR66## CF.sub.3 Br S Cl Cl ##STR67## iPr CF.sub.3 H O Cl F ##STR68## iPr CF.sub.3 H S Cl F ##STR69## iPr CF.sub.3 H O Cl Cl ##STR70## iPr CF.sub.3 H S Cl Cl ##STR71## iPr CF.sub.3 Br O Cl F ##STR72## iPr CF.sub.3 Br S Cl F ##STR73## iPr CF.sub.3 Br O Cl Cl ##STR74## iPr CF.sub.3 Br S Cl Cl ##STR75## CH.sub.2 CCH.sub.2 CF.sub.3 H O Cl F ##STR76## CH.sub.2 CCH.sub.2 CF.sub.3 H S Cl F ##STR77## CH.sub.2 CCH.sub.2 CF.sub.3 H O Cl Cl ##STR78## CH.sub.2 CCH.sub.2 CF.sub.3 H S Cl Cl ##STR79## CH.sub.2 CCH.sub.2 CF.sub.3 Br O Cl F ##STR80## CH.sub.2 CCH.sub.2 CF.sub.3 Br S Cl F ##STR81## CH.sub.2 CCH.sub.2 CF.sub.3 Br O Cl Cl ##STR82## CH.sub.2 CCH.sub.2 CF.sub.3 Br S Cl Cl ##STR83## ##STR84## CF.sub.3 H O Cl Cl ##STR85## ##STR86## CF.sub.3 H S Cl F ##STR87## ##STR88## CF.sub.3 H S Cl Cl ##STR89## CH.sub.2 Ph CF.sub.3 H O Cl F ##STR90## CH.sub.2 Ph CF.sub.3 H O Cl Cl ##STR91## CH.sub.2 Ph CF.sub.3 H S Cl F ##STR92## CH.sub.2 Ph CF.sub.3 H S Cl Cl ##STR93## H CF.sub.3 H O Cl Cl ##STR94## H CF.sub.3 H S Cl F ##STR95## H CF.sub.3 H S Cl Cl ##STR96## H CF.sub.3 H O Cl F ##STR97## iPr CF.sub.3 H O Cl Cl ##STR98## iPr CF.sub.3 H S Cl F ##STR99## iPr CF.sub.3 H S Cl Cl ##STR100## iPr CF.sub.3 H O Cl FCH.sub.2 CHCH.sub.2 ##STR101## CF.sub.3 H O Cl FCH.sub.2 CHCH.sub.2 ##STR102## CF.sub.3 H O Cl ClCH.sub.2 CHCH.sub.2 CH.sub.2 Ph CF.sub.3 H O Cl FCH.sub.2 CHCH.sub.2 CH.sub.2 Ph CF.sub.3 H O Cl ClCH.sub.2 CHCH.sub.2 CH.sub.2 CHCH.sub.2 CF.sub.3 H O Cl FCH.sub.2 CHCH.sub.2 CH.sub.2 CHCH.sub.2 CF.sub.3 H O Cl ClCHF.sub.2 H N(CH.sub.3).sub.2 H O Cl FCHF.sub.2 H N(CH.sub.3).sub.2 H S Cl FCHF.sub.2 H N(CH.sub.3).sub.2 H O Cl ClCHF.sub.2 H N(CH.sub.3).sub.2 H S Cl ClCHF.sub.2 H N(CH.sub.3).sub.2 Br O Cl FCHF.sub.2 H N(CH.sub.3).sub.2 Br S Cl FCHF.sub.2 H N(CH.sub.3).sub.2 Br O Cl ClCHF.sub.2 H N(CH.sub.3).sub.2 Br S Cl ClCHF.sub.2 CH.sub.2 Ph N(CH.sub.3).sub.2 H O Cl FCHF.sub.2 CH.sub.2 Ph N(CH.sub.3).sub.2 H S Cl FCHF.sub.2 CH.sub.2 Ph N(CH.sub.3).sub.2 H O Cl ClCHF.sub.2 CH.sub.2 Ph N(CH.sub.3).sub.2 H S Cl ClCHF.sub.2 CH.sub.2 Ph N(CH.sub.3).sub.2 Br O Cl FCHF.sub.2 CH.sub.2 Ph N(CH.sub.3).sub.2 Br S Cl FCHF.sub.2 CH.sub.2 Ph N(CH.sub.3).sub.2 Br O Cl ClCHF.sub.2 CH.sub.2 Ph N(CH.sub.3).sub.2 Br S Cl ClCHF.sub.2 ##STR103## N(CH.sub.3).sub.2 H O Cl FCHF.sub.2 ##STR104## N(CH.sub.3).sub.2 H S Cl FCHF.sub.2 ##STR105## N(CH.sub.3).sub.2 H O Cl ClCHF.sub.2 ##STR106## N(CH.sub.3).sub.2 H S Cl ClCHF.sub.2 ##STR107## N(CH.sub.3).sub.2 Br O Cl FCHF.sub.2 ##STR108## N(CH.sub.3).sub.2 Br S Cl FCHF.sub.2 ##STR109## N(CH.sub.3).sub.2 Br O Cl ClCHF.sub.2 ##STR110## N(CH.sub.3).sub.2 Br S Cl ClCHF.sub.2 iPr N(CH.sub.3).sub.2 H O Cl FCHF.sub.2 iPr N(CH.sub.3).sub.2 H S Cl FCHF.sub.2 iPr N(CH.sub.3).sub.2 H O Cl ClCHF.sub.2 iPr N(CH.sub.3).sub.2 H S Cl ClCHF.sub.2 iPr N(CH.sub.3).sub.2 Br O Cl FCHF.sub.2 iPr N(CH.sub.3).sub.2 Br S Cl FCHF.sub.2 iPr N(CH.sub.3).sub.2 Br O Cl ClCHF.sub.2 iPr N(CH.sub.3).sub.2 Br S Cl ClCHF.sub.2 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 H O Cl FCHF.sub.2 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 H S Cl FCHF.sub.2 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 H O Cl ClCHF.sub.2 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 H S Cl ClCHF.sub.2 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 Br O Cl FCHF.sub.2 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 Br S Cl FCHF.sub.2 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 Br O Cl ClCHF.sub.2 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 Br S Cl ClCH.sub.3 H N(CH.sub.3).sub.2 H O Cl FCH.sub.3 H N(CH.sub.3).sub.2 H S Cl FCH.sub.3 H N(CH.sub.3).sub.2 H O Cl ClCH.sub.3 H N(CH.sub.3).sub.2 H S Cl ClCH.sub.3 H N(CH.sub.3).sub.2 Br O Cl FCH.sub.3 H N(CH.sub.3).sub.2 Br S Cl FCH.sub.3 H N(CH.sub.3).sub.2 Br O Cl ClCH.sub.3 H N(CH.sub.3).sub.2 Br S Cl ClCH.sub.3 CH.sub.2 Ph N(CH.sub.3).sub.2 H O Cl FCH.sub.3 CH.sub.2 Ph N(CH.sub.3).sub.2 H S Cl FCH.sub.3 CH.sub.2 Ph N(CH.sub.3).sub.2 H O Cl ClCH.sub.3 CH.sub.2 Ph N(CH.sub.3).sub.2 H S Cl ClCH.sub.3 CH.sub.2 Ph N(CH.sub.3).sub.2 Br O Cl FCH.sub.3 CH.sub.2 Ph N(CH.sub.3).sub.2 Br S Cl FCH.sub.3 CH.sub.2 Ph N(CH.sub.3).sub.2 Br O Cl ClCH.sub.3 CH.sub.2 Ph N(CH.sub.3).sub.2 Br S Cl ClCH.sub.3 ##STR111## N CH.sub.3).sub.2 H O Cl FCH.sub.3 ##STR112## N(CH.sub.3).sub.2 H S Cl FCH.sub.3 ##STR113## N(CH.sub.3).sub.2 H O Cl ClCH.sub.3 ##STR114## N(CH.sub.3).sub.2 H S Cl ClCH.sub.3 ##STR115## N(CH.sub.3).sub.2 Br O Cl FCH.sub.3 ##STR116## N(CH.sub.3).sub.2 Br S Cl FCH.sub.3 ##STR117## N(CH.sub.3).sub.2 Br O Cl ClCH.sub.3 ##STR118## N(CH.sub.3).sub.2 Br S Cl ClCH.sub.3 iPr N(CH.sub.3).sub.2 H O Cl FCH.sub.3 iPr N(CH.sub.3).sub.2 H S Cl FCH.sub.3 iPr N(CH.sub.3).sub.2 H O Cl ClCH.sub.3 iPr N(CH.sub.3).sub.2 H S Cl ClCH.sub.3 iPr N(CH.sub.3).sub.2 Br O Cl FCH.sub.3 iPr N(CH.sub.3).sub.2 Br S Cl FCH.sub.3 iPr N(CH.sub.3).sub.2 Br O Cl ClCH.sub.3 iPr N(CH.sub.3).sub.2 Br S Cl ClCH.sub.3 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 H O Cl FCH.sub.3 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 H S Cl FCH.sub.3 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 H O Cl ClCH.sub.3 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 H S Cl ClCH.sub.3 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 Br O Cl FCH.sub.3 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 Br S Cl FCH.sub.3 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 Br O Cl ClCH.sub.3 CH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 Br S Cl ClCH.sub.3 CH.sub.2 Ph (CH.sub.2).sub.3 O Cl FCH.sub.3 CH.sub.2 Ph (CH.sub.2).sub.3 S Cl FCH.sub.3 CH.sub.2 Ph (CH.sub.2).sub.3 O Cl ClCH.sub.3 CH.sub.2 Ph (CH.sub.2).sub.3 S Cl ClCH.sub.3 ##STR119## (CH.sub.2).sub.3 O Cl FCH.sub.3 ##STR120## (CH.sub.2).sub.3 S Cl FCH.sub.3 ##STR121## (CH.sub.2).sub.3 O Cl ClCH.sub.3 ##STR122## (CH.sub.2).sub.3 S Cl ClCH.sub.3 iPr (CH.sub.2).sub.3 O Cl FCH.sub.3 iPr (CH.sub.2).sub.3 S Cl FCH.sub.3 iPr (CH.sub.2).sub.3 O Cl ClCH.sub.3 iPr (CH.sub.2).sub.3 S Cl ClCH.sub.3 CH.sub.2 Ph (CH.sub.2).sub.4 O Cl FCH.sub.3 CH.sub.2 Ph (CH.sub.2).sub.4 S Cl FCH.sub.3 CH.sub.2 Ph (CH.sub.2).sub.4 O Cl ClCH.sub.3 CH.sub.2 Ph (CH.sub.2).sub.4 S Cl ClCH.sub.3 ##STR123## (CH.sub.2).sub.4 O Cl FCH.sub.3 ##STR124## (CH.sub.2).sub.4 S Cl FCH.sub.3 ##STR125## (CH.sub.2).sub.4 O Cl ClCH.sub.3 ##STR126## (CH.sub.2).sub.4 S Cl ClCH.sub.3 iPr (CH.sub.2).sub.4 O Cl FCH.sub.3 iPr (CH.sub.2).sub.4 S Cl FCH.sub.3 iPr (CH.sub.2).sub.4 O Cl ClCH.sub.3 iPr (CH.sub.2).sub.4 S Cl ClCN ##STR127## CF.sub.3 H O Cl FCN ##STR128## CF.sub.3 H S Cl FCN ##STR129## N(CH.sub.3).sub.2 H O Cl ClCN ##STR130## N(CH.sub.3).sub.2 Br S Cl ClCOCH.sub.3 ##STR131## CF.sub.3 H O Cl FCOCH.sub.3 ##STR132## CF.sub.3 H S Cl FCOCH.sub.3 ##STR133## N(CH.sub.3).sub.2 H O Cl ClCOCH.sub.3 ##STR134## N(CH.sub.3).sub.2 Br S Cl ClCOCH.sub.3 iPr N(CH.sub.3).sub.2 H S Cl FCOCH.sub.3 iPr N(CH.sub.3).sub.2 H O Cl FCOCH.sub.3 iPr N(CH.sub.3).sub.2 H O Cl ClCOCH.sub.3 iPr N(CH.sub.3).sub.2 Br O Cl FCOCF.sub.3 ##STR135## CF.sub.3 H S Cl FCOCF.sub.3 ##STR136## CF.sub.3 H O Cl ClCOCF.sub.3 ##STR137## CF.sub.3 H O Cl FCOCF.sub.3 iPr N(CH.sub.3).sub.2 H S Cl FCOCF.sub.3 iPr N(CH.sub.3).sub.2 H O Cl ClCOCF.sub.3 iPr N(CH.sub.3).sub.2 H O Cl FOCH.sub.3 ##STR138## CF.sub.3 H O Cl FOCH.sub.3 ##STR139## CF.sub.3 H S Cl FOCH.sub.3 ##STR140## N(CH.sub.3).sub.2 H O Cl ClOCH.sub.3 ##STR141## N(CH.sub.3).sub.2 Br S Cl ClCF.sub.2 H ##STR142## CF.sub.3 H O Cl FCF.sub.2 H ##STR143## CF.sub.3 H S Cl FCF.sub.2 H ##STR144## N(CH.sub.3).sub.2 H O Cl ClCF.sub.2 H ##STR145## N(CH.sub.3).sub.2 Br S Cl ClCF.sub.2 H iPr N(CH.sub.3).sub.2 H S Cl FCF.sub.2 H iPr N(CH.sub.3).sub.2 H O Cl FCF.sub.2 H iPr N(CH.sub.3).sub.2 H O Cl ClCF.sub.2 H iPr N(CH.sub.3).sub.2 Br O Cl Fn-Bu ##STR146## CF.sub.3 H S Cl Fn-Bu ##STR147## CF.sub.3 H O Cl Cln-Bu ##STR148## CF.sub.3 H O Cl Fn-Bu iPr N(CH.sub.3).sub.2 H S Cl Fn-Bu iPr N(CH.sub.3).sub.2 H O Cl Cln-Bu iPr N(CH.sub.3).sub.2 H O Cl F ##STR149## ##STR150## CF.sub.3 H S Cl F ##STR151## ##STR152## CF.sub.3 H O Cl Cl ##STR153## ##STR154## CF.sub.3 H O Cl F ##STR155## ##STR156## N(CH.sub.3).sub.2 H S Cl F ##STR157## ##STR158## N(CH.sub.3).sub.2 H O Cl Cl ##STR159## ##STR160## N(CH.sub.3).sub.2 H O Cl F ##STR161## iPr CF.sub.3 H S Cl F ##STR162## iPr CF.sub.3 H O Cl Cl ##STR163## iPr CF.sub.3 H O Cl F ##STR164## iPr N(CH.sub.3).sub.2 H S Cl F ##STR165## iPr N(CH.sub.3).sub.2 H O Cl Cl ##STR166## iPr N(CH.sub.3).sub.2 H O Cl FCH.sub.2 CMeCH.sub.2 ##STR167## N(CH.sub.3).sub.2 H S Cl FCH.sub.2 CMeCH.sub.2 ##STR168## N(CH.sub.3).sub.2 H O Cl ClCH.sub.2 CMeCH.sub.2 ##STR169## N(CH.sub.3).sub.2 H S Cl FCH.sub.2 CMeCH.sub.2 ##STR170## CF.sub.3 H O Cl ClCH.sub.2 CMeCH.sub.2 ##STR171## CF.sub.3 H S Cl FCH.sub.2 CMeCH.sub.2 ##STR172## CF.sub.3 H O Cl ClCH.sub.2 CMeCH.sub.2 iPr N(CH.sub.3).sub.2 H S Cl FCH.sub.2 CMeCH.sub.2 iPr N(CH.sub.3).sub.2 H O Cl ClCH.sub.2 CMeCH.sub.2 iPr N(CH.sub.3).sub.2 H S Cl FCH.sub.2 CMeCH.sub.2 iPr CF.sub.3 H O Cl ClCH.sub.2 CMeCH.sub.2 iPr CF.sub.3 H S Cl FCH.sub.2 CMeCH.sub.2 iPr CF.sub.3 H O Cl ClCH.sub.2 CMeCH.sub.2 ##STR173## N(CH.sub.3).sub.2 H S Cl FCH.sub.2 CMeCH.sub.2 ##STR174## N(CH.sub.3).sub.2 H O Cl ClCH.sub.2 CMeCH.sub.2 ##STR175## N(CH.sub.3).sub.2 H S Cl FCH.sub.2 CMeCH.sub.2 ##STR176## CF.sub.3 H O Cl ClCH.sub.2 CMeCH.sub.2 ##STR177## CF.sub.3 H S Cl FCH.sub.2 CMeCH.sub.2 ##STR178## CF.sub.3 H O Cl CliPr iPr N(CH.sub.3).sub.2 H S Cl FiPr iPr N(CH.sub.3).sub.2 H O Cl CliPr iPr N(CH.sub.3).sub.2 H S Cl FiPr iPr CF.sub.3 H O Cl CliPr iPr CF.sub.3 H S Cl FiPr iPr CF.sub.3 H O Cl Cl______________________________________
TABLE II______________________________________ ##STR179##R.sup.1 R.sup.3 R.sup.4 A X Y R.sup.9______________________________________CH.sub.3 CF.sub.3 H O Cl FCH.sub.3 CF.sub.3 H S Cl FCH.sub.3 CF.sub.3 H O Cl ClCH.sub.3 CF.sub.3 H S Cl ClCH.sub.3 N(CH.sub.3).sub.2 H O Cl FCH.sub.3 N(CH.sub.3).sub.2 H S Cl FCH.sub.3 N(CH.sub.3).sub.2 H O Cl ClCH.sub.3 N(CH.sub.3).sub.2 H S Cl ClCH.sub.3 CF.sub.3 Br O Cl FCH.sub.3 CF.sub.3 Br S Cl FCH.sub.3 CF.sub.3 Br O Cl ClCH.sub.3 CF.sub.3 Br S Cl ClCH.sub.3 N(CH.sub.3).sub.2 Br O Cl FCH.sub.3 N(CH.sub.3).sub.2 Br S Cl FCH.sub.3 N(CH.sub.3).sub.2 Br O Cl ClCH.sub.3 N(CH.sub.3).sub.2 Br S Cl ClCH.sub.3 (CH.sub.2).sub.3 O Cl FCH.sub.3 (CH.sub.2).sub.3 O Cl ClCH.sub.3 (CH.sub.2).sub.3 S Cl FCH.sub.3 (CH.sub.2).sub.3 S Cl ClCH.sub.3 (CH.sub.2).sub.4 O Cl FCH.sub.3 (CH.sub.2).sub.4 O Cl FCH.sub.3 (CH.sub.2).sub.4 S Cl FCH.sub.3 (CH.sub.2).sub.4 S Cl FCF.sub.3 CF.sub.3 H O Cl FCF.sub.3 CF.sub.3 H S Cl FCF.sub.3 CF.sub.3 H O Cl ClCF.sub.3 CF.sub.3 H S Cl ClCF.sub.3 N(CH.sub.3).sub.2 H O Cl FCF.sub.3 N(CH.sub.3).sub.2 H S Cl FCF.sub.3 N(CH.sub.3).sub.2 H O Cl ClCF.sub.3 N(CH.sub.3).sub.2 H S Cl ClCF.sub.3 CF.sub.3 Br O Cl FCF.sub.3 CF.sub.3 Br S Cl FCF.sub.3 CF.sub.3 Br O Cl ClCF.sub.3 CF.sub.3 Br S Cl ClCF.sub.3 N(CH.sub.3).sub.2 Br O Cl FCF.sub.3 N(CH.sub.3).sub.2 Br S Cl FCF.sub.3 N(CH.sub.3).sub.2 Br O Cl ClCF.sub.3 N(CH.sub.3).sub.2 Br S Cl ClCF.sub.3 (CH.sub.2).sub.3 O Cl FCF.sub.3 (CH.sub.2).sub.3 O Cl ClCF.sub.3 (CH.sub.2).sub.3 S Cl FCF.sub.3 (CH.sub.2).sub.3 S Cl ClCF.sub.3 (CH.sub.2).sub.4 O Cl FCF.sub.3 (CH.sub.2).sub.4 O Cl FCF.sub.3 (CH.sub.2).sub.4 S Cl FCF.sub.3 (CH.sub.2).sub.4 S Cl FCH.sub.2 CCH.sub.2 CF.sub.3 H O Cl FCH.sub.2 CCH.sub.2 CF.sub.3 H S Cl FCH.sub.2 CCH.sub.2 CF.sub.3 H O Cl ClCH.sub.2 CCH.sub.2 CF.sub.3 H O Cl FCH.sub.2 CCH.sub.2 CHF.sub.2 H O Cl FCH.sub.2 CCH.sub.2 CHF.sub.2 H O Cl ClCH.sub.2 CCH.sub.2 CHF.sub.2 H S Cl FCH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 H O Cl FCH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 H S Cl FCH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 H O Cl ClCH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 H S Cl ClCH.sub.2 CCH.sub.2 CF.sub.3 Br O Cl FCH.sub.2 CCH.sub.2 CF.sub.3 Br S Cl FCH.sub.2 CCH.sub.2 CF.sub.3 Br O Cl ClCH.sub.2 CCH.sub.2 CF.sub.3 Br S Cl ClCH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 Br O Cl FCH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 Br S Cl FCH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 Br O Cl ClCH.sub.2 CCH.sub.2 N(CH.sub.3).sub.2 Br S Cl ClCH.sub.2 CCH.sub.2 (CH.sub.2).sub.3 O Cl FCH.sub.2 CCH.sub.2 (CH.sub.2).sub.3 O Cl ClCH.sub.2 CCH.sub.2 (CH.sub.2).sub.3 S Cl FCH.sub.2 CCH.sub.2 (CH.sub.2).sub.3 S Cl ClCH.sub.2 CCH.sub.2 (CH.sub.2).sub.4 O Cl FCH.sub.2 CCH.sub.2 (CH.sub.2).sub.4 O Cl FCH.sub.2 CCH.sub.2 (CH.sub.2).sub.4 S Cl FCH.sub.2 CCH.sub.2 (CH.sub.2).sub.4 S Cl F ##STR180## CF.sub.3 H O Cl F ##STR181## CF.sub.3 H S Cl F ##STR182## CF.sub.3 H O Cl Cl ##STR183## CF.sub.3 H O Cl F ##STR184## CHF.sub.2 H O Cl F ##STR185## CHF.sub.2 H O Cl Cl ##STR186## CHF.sub.2 H S Cl F ##STR187## N(CH.sub.3).sub.2 H O Cl F ##STR188## N(CH.sub.3).sub.2 H S Cl F ##STR189## N(CH.sub.3).sub.2 H O Cl Cl ##STR190## N(CH.sub.3).sub.2 H S Cl Cl ##STR191## CF.sub.3 Br O Cl F ##STR192## CF.sub.3 Br S Cl F ##STR193## CF.sub.3 Br O Cl Cl ##STR194## CF.sub.3 Br S Cl Cl ##STR195## N(CH.sub.3).sub.2 Br O Cl F ##STR196## N(CH.sub.3).sub.2 Br S Cl F ##STR197## N(CH.sub.3).sub.2 Br O Cl Cl ##STR198## N(CH.sub.3).sub.2 Br S Cl Cl ##STR199## (CH.sub.2).sub.3 O Cl F ##STR200## (CH.sub.2).sub.3 O Cl Cl ##STR201## (CH.sub.2).sub.3 S Cl F ##STR202## (CH.sub.2).sub.3 S Cl Cl ##STR203## (CH.sub.2).sub.4 O Cl F ##STR204## (CH.sub.2).sub.4 O Cl F ##STR205## (CH.sub.2).sub.4 S Cl F ##STR206## (CH.sub.2).sub.4 S Cl F ##STR207## CF.sub.3 F O Cl F ##STR208## CF.sub.3 F O Cl Cln-Bu CF.sub.3 H O Cl Fn-Bu CF.sub.3 H S Cl FCOCH.sub.3 CF.sub.3 H O Cl FCOCH.sub.3 CF.sub.3 H O Cl ClCN CF.sub.3 H O Cl FCN CF.sub.3 H O Cl ClCHF.sub.2 CF.sub.3 H O Cl FCHF.sub.2 CF.sub.3 H O Cl ClCH.sub.3 CHF.sub.2 Br O Cl FCH.sub.3 CHF.sub.2 Br S Cl FCH.sub.3 CF.sub.3 F O Cl FCH.sub.3 CF.sub.3 F S Cl FCH.sub.3 CHF.sub.2 F O Cl FCH.sub.3 CHF.sub.2 F S Cl FCH.sub.3 CH.sub.2 F F O Cl FCH.sub.3 CH.sub.2 F F S Cl FCH.sub.3 CF.sub.3 Cl O Cl FCH.sub.3 CF.sub.3 Cl S Cl FCH.sub.3 CF.sub.3 Cl O Cl FCH.sub.3 CF.sub.3 Cl S Cl FCH.sub.3 CF.sub.3 H O Cl F CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 H S Cl F CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 H O Cl Cl CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 H S Cl Cl CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 H O Cl F CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 H S Cl F CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 H O Cl Cl CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 H S Cl Cl CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 H O Cl F CF.sub.3CH.sub.3 CF.sub.3 H S Cl F CF.sub.3CH.sub.3 CF.sub.3 H O Cl Cl CF.sub.3CH.sub.3 CF.sub.3 H S Cl Cl CF.sub.3CH.sub.3 CF.sub.3 H O Cl F CF.sub.2 HCH.sub.3 CF.sub.3 H S Cl F CF.sub.2 HCH.sub.3 CF.sub.3 H O Cl Cl CF.sub.2 HCH.sub.3 CF.sub.3 H S Cl Cl CF.sub.2 HCH.sub.3 CF.sub.3 H O Cl F CFH.sub.2CH.sub.3 CF.sub.3 H S Cl F CFH.sub.2CH.sub.3 CF.sub.3 H O Cl Cl CFH.sub.2CH.sub.3 CF.sub.3 H S Cl Cl CFH.sub.2CH.sub.3 CF.sub.3 H O Cl F CHCH.sub.2CH.sub.3 CF.sub.3 H S Cl F CHCH.sub.2CH.sub.3 CF.sub.3 H O Cl Cl CHCH.sub.2CH.sub.3 CF.sub.3 H S Cl Cl CHCH.sub.2CH.sub.3 CF.sub.3 H O Cl F ##STR209##CH.sub.3 CF.sub.3 H S Cl F ##STR210##CH.sub.3 CF.sub.3 H O Cl Cl ##STR211##CH.sub.3 CF.sub.3 H S Cl Cl ##STR212##CH.sub.3 CF.sub.3 H O Cl F CNCH.sub.3 CF.sub.3 H S Cl F CNCH.sub.3 CF.sub.3 H O Cl Cl CNCH.sub.3 CF.sub.3 H S Cl Cl CNCF.sub.3 CF.sub.3 H O Cl F CH.sub.2 CH.sub.3CF.sub.3 CF.sub.3 H S Cl F CH.sub.2 CH.sub.3CF.sub.3 CF.sub.3 H O Cl Cl CH.sub.2 CH.sub.3CF.sub.3 CF.sub.3 H S Cl Cl CH.sub.2 CH.sub.3CF.sub.3 CF.sub.3 H O Cl F CH.sub.2 CH.sub.2 CH.sub.3CF.sub.3 CF.sub.3 H S Cl F CH.sub.2 CH.sub.2 CH.sub.3CF.sub.3 CF.sub.3 H O Cl Cl CH.sub.2 CH.sub.2 CH.sub.3CF.sub.3 CF.sub.3 H S Cl Cl CH.sub.2 CH.sub.2 CH.sub.3CF.sub.3 CF.sub.3 H O Cl F CF.sub.3CF.sub.3 CF.sub.3 H S Cl F CF.sub.3CF.sub.3 CF.sub.3 H O Cl Cl CF.sub.3CF.sub.3 CF.sub.3 H S Cl Cl CF.sub.3CF.sub.3 CF.sub.3 H O Cl F CF.sub.2 HCF.sub.3 CF.sub.3 H S Cl F CF.sub.2 HCF.sub.3 CF.sub.3 H O Cl Cl CF.sub.2 HCF.sub.3 CF.sub.3 H S Cl Cl CF.sub.2 HCF.sub.3 CF.sub.3 H O Cl F CFH.sub.2CF.sub.3 CF.sub.3 H S Cl F CFH.sub.2CF.sub.3 CF.sub.3 H O Cl Cl CFH.sub.2CF.sub.3 CF.sub.3 H S Cl Cl CFH.sub.2CF.sub.3 CF.sub.3 H O Cl F CHCH.sub.2CF.sub.3 CF.sub.3 H S Cl F CHCH.sub.2CF.sub.3 CF.sub.3 H O Cl Cl CHCH.sub.2CF.sub.3 CF.sub.3 H S Cl Cl CHCH.sub.2CF.sub.3 CF.sub.3 H O Cl F ##STR213##CF.sub.3 CF.sub.3 H S Cl F ##STR214##CF.sub.3 CF.sub.3 H O Cl Cl ##STR215##CF.sub.3 CF.sub.3 H S Cl Cl ##STR216##CF.sub.3 CF.sub.3 H O Cl F CNCF.sub.3 CF.sub.3 H S Cl F CNCF.sub.3 CF.sub.3 H O Cl Cl CNCF.sub.3 CF.sub.3 H S Cl Cl CNCH.sub.3 CF.sub.3 Br O Cl F CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 Br S Cl F CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 Br O Cl Cl CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 Br S Cl Cl CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 Br O Cl F CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 Br S Cl F CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 Br O Cl Cl CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 Br S Cl Cl CH.sub.2 CH.sub.2 CH.sub.3CH.sub.3 CF.sub.3 Br O Cl F CF.sub.3CH.sub.3 CF.sub.3 Br S Cl F CF.sub.3CH.sub.3 CF.sub.3 Br O Cl Cl CF.sub.3CH.sub.3 CF.sub.3 Br S Cl Cl CF.sub.3CH.sub.3 CF.sub.3 Br O Cl F CF.sub.2 HCH.sub.3 CF.sub.3 Br S Cl F CF.sub.2 HCH.sub.3 CF.sub.3 Br O Cl Cl CF.sub.2 HCH.sub.3 CF.sub.3 Br S Cl Cl CF.sub.2 HCH.sub.3 CF.sub.3 Br O Cl F CFH.sub.2CH.sub.3 CF.sub.3 Br S Cl F CFH.sub.2CH.sub.3 CF.sub.3 Br O Cl Cl CFH.sub.2CH.sub.3 CF.sub.3 Br S Cl Cl CFH.sub.2CH.sub.3 CF.sub.3 Br O Cl F CHCH.sub.2CH.sub.3 CF.sub.3 Br S Cl F CHCH.sub.2CH.sub.3 CF.sub.3 Br O Cl Cl CHCH.sub.2CH.sub.3 CF.sub.3 Br S Cl Cl CHCH.sub.2CH.sub.3 CF.sub.3 Br O Cl F ##STR217##CH.sub.3 CF.sub.3 Br S Cl F ##STR218##CH.sub.3 CF.sub.3 Br O Cl Cl ##STR219##CH.sub.3 CF.sub.3 Br S Cl Cl ##STR220##CH.sub.3 CF.sub.3 Cl O Cl F CHCH.sub.2CH.sub.3 CF.sub.3 Cl S Cl F CHCH.sub.2CH.sub.3 CF.sub.3 Cl O Cl Cl CHCH.sub.2CH.sub.3 CF.sub.3 Cl S Cl Cl CHCH.sub.2CH.sub.3 CF.sub.3 Cl O Cl F ##STR221##CH.sub.3 CF.sub.3 Cl S Cl F ##STR222##CH.sub.3 CF.sub.3 Cl O Cl Cl ##STR223##CH.sub.3 CF.sub.3 Cl S Cl Cl ##STR224##CH.sub.3 CF.sub.3 Br O Cl F CNCH.sub.3 CF.sub.3 Br S Cl F CNCH.sub.3 CF.sub.3 Br O Cl Cl CNCH.sub.3 CF.sub.3 Br S Cl Cl CNCH.sub.3 (CH.sub.2).sub.3 O Cl F CH.sub.2 CH.sub.3CH.sub.3 (CH.sub.2).sub.3 S Cl F CH.sub.2 CH.sub.3CH.sub.3 (CH.sub.2).sub.3 O Cl Cl CH.sub.2 CH.sub.3CH.sub.3 (CH.sub.2).sub.3 S Cl Cl CH.sub.2 CH.sub.3CH.sub.3 (CH.sub.2).sub.4 O Cl F CH.sub.2 CH.sub.3CH.sub.3 (CH.sub.2).sub.4 S Cl F CH.sub.2 CH.sub.3CH.sub.3 (CH.sub.2).sub.4 O Cl Cl CH.sub.2 CH.sub.3CH.sub.3 (CH.sub.2).sub.4 S Cl Cl CH.sub.2 CH.sub.3CH.sub.3 (CH.sub.2).sub.3 O Cl F CF.sub.3CH.sub.3 (CH.sub.2).sub.3 S Cl F CF.sub.3CH.sub.3 (CH.sub.2).sub.3 O Cl Cl CF.sub.3CH.sub.3 (CH.sub.2).sub.3 S Cl Cl CF.sub.3CH.sub.3 (CH.sub.2).sub.4 S Cl F CF.sub.3CH.sub.3 (CH.sub.2).sub.4 O Cl F CF.sub.3CH.sub.3 (CH.sub.2).sub.4 S Cl Cl CF.sub.3CH.sub.3 (CH.sub.2).sub.4 O Cl Cl CF.sub.3CH.sub.3 (CH.sub.2).sub.3 O Cl F CF.sub.2 HCH.sub.3 (CH.sub.2).sub.3 S Cl F CF.sub.2 HCH.sub.3 (CH.sub.2).sub.3 O Cl Cl CF.sub.2 HCH.sub.3 (CH.sub.2).sub.3 S Cl Cl CF.sub.2 HCH.sub.3 (CH.sub.2).sub.4 O Cl F CF.sub.2 HCH.sub.3 (CH.sub.2).sub.4 S Cl F CF.sub.2 HCH.sub.3 (CH.sub.2).sub.4 O Cl Cl CF.sub.2 HCH.sub.3 (CH.sub.2).sub.4 S Cl Cl CF.sub.2 HCH.sub.3 (CH.sub.2).sub.3 O Cl F CFH.sub.2CH.sub.3 (CH.sub.2).sub.3 S Cl F CFH.sub.2CH.sub.3 (CH.sub.2).sub.3 O Cl Cl CFH.sub.2CH.sub.3 (CH.sub.2).sub.3 S Cl Cl CFH.sub.2CH.sub.3 (CH.sub.2).sub.4 O Cl F CFH.sub.2CH.sub.3 (CH.sub.2).sub.4 S Cl F CFH.sub.2CH.sub.3 (CH.sub.2).sub.4 O Cl Cl CFH.sub.2CH.sub.3 (CH.sub.2).sub.4 S Cl Cl CFH.sub.2CH.sub.3 (CH.sub.2).sub.3 O Cl F CHCH.sub.2CH.sub.3 (CH.sub.2).sub.3 S Cl F CHCH.sub.2CH.sub.3 (CH.sub.2).sub.3 O Cl Cl CHCH.sub.2CH.sub.3 (CH.sub.2).sub.3 S Cl Cl CHCH.sub.2CH.sub.3 (CH.sub.2).sub.4 O Cl F CHCH.sub.2CH.sub.3 (CH.sub.2).sub.4 S Cl F CHCH.sub.2CH.sub.3 (CH.sub.2).sub.4 O Cl Cl CHCH.sub.2CH.sub.3 (CH.sub.2).sub.4 S Cl Cl CHCH.sub.2CH.sub.3 (CH.sub.2).sub.3 O Cl F ##STR225##CH.sub.3 (CH.sub.2).sub.3 S Cl F ##STR226##CH.sub.3 (CH.sub.2).sub.3 O Cl Cl ##STR227##CH.sub.3 (CH.sub.2).sub.3 S Cl Cl ##STR228##CH.sub.3 (CH.sub.2).sub.4 O Cl F ##STR229##CH.sub.3 (CH.sub.2).sub.4 S Cl F ##STR230##CH.sub.3 (CH.sub.2).sub.4 O Cl Cl ##STR231##CH.sub.3 (CH.sub.2).sub.4 S Cl Cl ##STR232##CH.sub.3 (CH.sub.2).sub.3 O Cl F CNCH.sub.3 (CH.sub.2).sub.3 S Cl F CNCH.sub.3 (CH.sub.2).sub.3 O Cl Cl CNCH.sub.3 (CH.sub.2).sub.3 S Cl Cl CNCH.sub.3 (CH.sub.2).sub.4 O Cl F CNCH.sub.3 (CH.sub.2).sub.4 S Cl F CNCH.sub.3 (CH.sub.2).sub.4 O Cl Cl CNCH.sub.3 (CH.sub.2).sub.4 S Cl Cl CNCH.sub.3 CF.sub.3 H O Cl F CH.sub.2 OHCH.sub.3 CF.sub.3 H O Cl F CH.sub.2 OC(O)CH.sub.3CH.sub.3 CF.sub.3 H O Cl F CO.sub.2 CH.sub.3CH.sub.3 CF.sub.3 H O Cl F CON(CH.sub.3).sub.2CH.sub.3 N(CH.sub.3).sub.2 H O Cl F CH.sub.2 OHCH.sub.3 N(CH.sub.3).sub.2 H O Cl F CH.sub.2 OC(O)CH.sub.3CH.sub.3 N(CH.sub.3).sub.2 H O Cl F CO.sub.2 CH.sub.3CH.sub.3 CF.sub.3 Br O Cl F CH.sub.2 OHCH.sub.3 CF.sub.3 Br O Cl F CH.sub.2 OC(O)CH.sub.3CH.sub.3 CF.sub.3 Br O Cl F CO.sub.2 CH.sub.3CH.sub.3 CF.sub.3 Br S Cl F CH.sub.2 OH______________________________________
TABLE III______________________________________ ##STR233##R.sup.1 R.sup.3 A X Y R.sup.2 Z______________________________________CH.sub.3 N(CH.sub.3).sub.2 O Cl F H HCH.sub.3 N(CH.sub.3).sub.2 O Cl Cl H HCH.sub.3 N(CH.sub.3).sub.2 S Cl F H HCH.sub.3 N(CH.sub.3).sub.2 S Cl Cl H HCH.sub.3 N(CH.sub.3).sub.2 O Cl F ##STR234## HCH.sub.3 N(CH.sub.3).sub.2 O Cl Cl ##STR235## HCH.sub.3 N(CH.sub.3).sub.2 S Cl F ##STR236## HCH.sub.3 N(CH.sub.3).sub.2 S Cl Cl ##STR237## HCH.sub.3 N(CH.sub.3).sub.2 O Cl F CH.sub.2 Ph HCH.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH.sub.2 Ph HCH.sub.3 N(CH.sub.3).sub.2 S Cl F CH.sub.2 Ph HCH.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH.sub.2 Ph HCH.sub.3 N(CH.sub.3).sub.2 O Cl F iPr HCH.sub.3 N(CH.sub.3).sub.2 O Cl Cl iPr HCH.sub.3 N(CH.sub.3).sub.2 S Cl F iPr HCH.sub.3 N(CH.sub.3).sub.2 S Cl Cl iPr HCH.sub.3 N(CH.sub.3).sub.2 O Cl F ##STR238## HCH.sub.3 N(CH.sub.3).sub.2 O Cl Cl ##STR239## HCH.sub.3 N(CH.sub.3).sub.2 S Cl F ##STR240## HCH.sub.3 N(CH.sub.3).sub.2 S Cl Cl ##STR241## HCH.sub.3 N(CH.sub.3).sub.2 O Cl F CH.sub.2 CHCH.sub.2 HCH.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH.sub.2 CHCH.sub.2 HCH.sub.3 N(CH.sub.3).sub.2 S Cl F CH.sub.2 CHCH.sub.2 HCH.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH.sub.2 CHCH.sub.2 HCH.sub.3 N(CH.sub.3).sub.2 O Cl F CHMeCO.sub.2 Me HCH.sub.3 N(CH.sub.3).sub.2 O Cl Cl CHMeCO.sub.2 Me HCH.sub.3 N(CH.sub.3).sub.2 S Cl F CHMeCO.sub.2 Me HCH.sub.3 N(CH.sub.3).sub.2 S Cl Cl CHMeCO.sub.2 Me HCH.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CH.sub.3)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.3)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CH.sub.3)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CH.sub.3)CH.sub.2CH.sub.3 CF.sub.3 O Cl F H HCH.sub.3 CF.sub.3 O Cl Cl H HCH.sub.3 CF.sub.3 S Cl F H HCH.sub.3 CF.sub.3 S Cl Cl H HCH.sub.3 CF.sub.3 O Cl F ##STR242## HCH.sub.3 CF.sub.3 O Cl Cl ##STR243## HCH.sub.3 CF.sub.3 S Cl F ##STR244## HCH.sub.3 CF.sub.3 S Cl Cl ##STR245## HCH.sub.3 CF.sub.3 O Cl F CH.sub.2 Ph HCH.sub.3 CF.sub.3 O Cl Cl CH.sub.2 Ph HCH.sub.3 CF.sub.3 S Cl F CH.sub.2 Ph HCH.sub.3 CF.sub.3 S Cl Cl CH.sub.2 Ph HCH.sub.3 CF.sub.3 O Cl F iPr HCH.sub.3 CF.sub.3 O Cl Cl iPr HCH.sub.3 CF.sub.3 S Cl F iPr HCH.sub.3 CF.sub.3 S Cl Cl iPr HCH.sub.3 CF.sub.3 O Cl F ##STR246## HCH.sub.3 CF.sub.3 O Cl Cl ##STR247## HCH.sub.3 CF.sub.3 S Cl F ##STR248## HCH.sub.3 CF.sub.3 S Cl Cl ##STR249## HCH.sub.3 CF.sub.3 O Cl F CH.sub.2 CHCH.sub.2 HCH.sub.3 CF.sub.3 O Cl Cl CH.sub.2 CHCH.sub.2 HCH.sub.3 CF.sub.3 S Cl F CH.sub.2 CHCH.sub.2 HCH.sub.3 CF.sub.3 S Cl Cl CH.sub.2 CHCH.sub.2 HCH.sub.3 CF.sub.3 O Cl F CHMeCO.sub.2 Me HCH.sub.3 CF.sub.3 O Cl Cl CHMeCO.sub.2 Me HCH.sub.3 CF.sub.3 S Cl F CHMeCO.sub.2 Me HCH.sub.3 CF.sub.3 S Cl Cl CHMeCO.sub.2 Me HCH.sub.3 CF.sub.3 O Cl F CH(CH.sub.3)CH.sub.2CH.sub.3 CF.sub.3 O Cl Cl CH(CH.sub.3)CH.sub.2CH.sub.3 CF.sub.3 S Cl F CH(CH.sub.3)CH.sub.2CH.sub.3 CF.sub.3 S Cl Cl CH(CH.sub.3)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl F H HCF.sub.3 N(CH.sub.3).sub.2 O Cl Cl H HCF.sub.3 N(CH.sub.3).sub.2 S Cl F H HCF.sub.3 N(CH.sub.3).sub.2 S Cl Cl H HCF.sub.3 N(CH.sub.3).sub.2 O Cl F ##STR250## HCF.sub.3 N(CH.sub.3).sub.2 O Cl Cl ##STR251## HCF.sub.3 N(CH.sub.3).sub.2 S Cl F ##STR252## HCF.sub.3 N(CH.sub.3).sub.2 S Cl Cl ##STR253## HCF.sub.3 N(CH.sub.3).sub.2 O Cl F CH.sub.2 Ph HCF.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH.sub.2 Ph HCF.sub.3 N(CH.sub.3).sub.2 S Cl F CH.sub.2 Ph HCF.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH.sub.2 Ph HCF.sub.3 N(CH.sub.3).sub.2 O Cl F iPr HCF.sub.3 N(CH.sub.3).sub.2 O Cl Cl iPr HCF.sub.3 N(CH.sub.3).sub.2 S Cl F iPr HCF.sub.3 N(CH.sub.3).sub.2 S Cl Cl iPr HCF.sub.3 N(CH.sub.3).sub.2 O Cl F ##STR254## HCF.sub.3 N(CH.sub.3).sub.2 O Cl Cl ##STR255## HCF.sub.3 N(CH.sub.3).sub.2 S Cl F ##STR256## HCF.sub.3 N(CH.sub.3).sub.2 S Cl Cl ##STR257## HCF.sub.3 N(CH.sub.3).sub.2 O Cl F CH.sub.2 CHCH.sub.2 HCF.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH.sub.2 CHCH.sub.2 HCF.sub.3 N(CH.sub.3).sub.2 S Cl F CH.sub.2 CHCH.sub.2 HCF.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH.sub.2 CHCH.sub.2 HCF.sub.3 N(CH.sub.3).sub.2 O Cl F CHMeCO.sub.2 Me HCF.sub.3 N(CH.sub.3).sub.2 O Cl Cl CHMeCO.sub.2 Me HCF.sub.3 N(CH.sub.3).sub.2 S Cl F CHMeCO.sub.2 Me HCF.sub.3 N(CH.sub.3).sub.2 S Cl Cl CHMeCO.sub.2 Me HCF.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CH.sub.3)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.3)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CH.sub.3)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CH.sub.3)CH.sub.2CF.sub.3 CF.sub.3 O Cl F H HCF.sub.3 CF.sub.3 O Cl Cl H HCF.sub.3 CF.sub.3 S Cl F H HCF.sub.3 CF.sub.3 S Cl Cl H HCF.sub.3 CF.sub.3 O Cl F ##STR258## HCF.sub.3 CF.sub.3 O Cl Cl ##STR259## HCF.sub.3 CF.sub.3 S Cl F ##STR260## HCF.sub.3 CF.sub.3 S Cl Cl ##STR261## HCF.sub.3 CF.sub.3 O Cl F CH.sub.2 Ph HCF.sub.3 CF.sub.3 O Cl Cl CH.sub.2 Ph HCF.sub.3 CF.sub.3 S Cl F CH.sub.2 Ph HCF.sub.3 CF.sub.3 S Cl Cl CH.sub.2 Ph HCF.sub.3 CF.sub.3 O Cl F Pr HCF.sub.3 CF.sub.3 O Cl Cl Pr HCF.sub.3 CF.sub.3 S Cl F Pr HCF.sub.3 CF.sub.3 S Cl Cl Pr HCF.sub.3 CF.sub.3 O Cl F ##STR262## HCF.sub.3 CF.sub.3 O Cl Cl ##STR263## HCF.sub.3 CF.sub.3 S Cl F ##STR264## HCF.sub.3 CF.sub.3 S Cl Cl ##STR265## HCF.sub.3 CF.sub.3 O Cl F CH.sub.2 CHCH.sub.2 HCF.sub.3 CF.sub.3 O Cl Cl CH.sub.2 CHCH.sub.2 HCF.sub.3 CF.sub.3 S Cl F CH.sub.2 CHCH.sub.2 HCF.sub.3 CF.sub.3 S Cl Cl CH.sub.2 CHCH.sub.2 HCF.sub.3 CF.sub.3 O Cl F CHMeCO.sub.2 Me HCF.sub.3 CF.sub.3 O Cl Cl CHMeCO.sub.2 Me HCF.sub.3 CF.sub.3 S Cl F CHMeCO.sub.2 Me HCF.sub.3 CF.sub.3 S Cl Cl CHMeCO.sub.2 Me HCF.sub.3 CF.sub.3 O Cl F CH(CH.sub.3)CH.sub.2CF.sub.3 CF.sub.3 O Cl Cl CH(CH.sub.3)CH.sub.2CF.sub.3 CF.sub.3 S Cl F CH(CH.sub.3)CH.sub.2CF.sub.3 CF.sub.3 S Cl Cl CH(CH.sub.3)CH.sub.2i-Pr N(CH.sub.3).sub.2 O Cl F H Hi-Pr N(CH.sub.3).sub.2 O Cl Cl H Hi-Pr N(CH.sub.3).sub.2 S Cl F H Hi-Pr N(CH.sub.3).sub.2 S Cl Cl H Hi-Pr N(CH.sub.3).sub.2 O Cl F ##STR266## Hi-Pr N(CH.sub.3).sub.2 O Cl Cl ##STR267## Hi-Pr N(CH.sub.3).sub.2 S Cl F ##STR268## Hi-Pr N(CH.sub.3).sub.2 S Cl Cl ##STR269## Hi-Pr N(CH.sub.3).sub.2 O Cl F CH.sub.2 Ph Hi-Pr N(CH.sub.3).sub.2 O Cl Cl CH.sub.2 Ph Hi-Pr N(CH.sub.3).sub.2 S Cl F CH.sub.2 Ph Hi-Pr N(CH.sub.3).sub.2 S Cl Cl CH.sub.2 Ph Hi-Pr N(CH.sub.3).sub.2 O Cl F iPr Hi-Pr N(CH.sub.3).sub.2 O Cl Cl iPr Hi-Pr N(CH.sub.3).sub.2 S Cl F iPr Hi-Pr N(CH.sub.3).sub.2 S Cl Cl iPr Hi-Pr N(CH.sub.3).sub.2 O Cl F ##STR270## Hi-Pr N(CH.sub.3).sub.2 O Cl Cl ##STR271## Hi-Pr N(CH.sub.3).sub.2 S Cl F ##STR272## Hi-Pr N(CH.sub.3).sub.2 S Cl Cl ##STR273## Hi-Pr N(CH.sub.3).sub.2 O Cl F CH.sub.2 CHCH.sub.2 Hi-Pr N(CH.sub.3).sub.2 O Cl Cl CH.sub.2 CHCH.sub.2 Hi-Pr N(CH.sub.3).sub.2 S Cl F CH.sub.2 CHCH.sub.2 Hi-Pr N(CH.sub.3).sub.2 S Cl Cl CH.sub.2 CHCH.sub.2 Hi-Pr N(CH.sub.3).sub.2 O Cl F CHMeCO.sub.2 Me Hi-Pr N(CH.sub.3).sub.2 O Cl Cl CHMeCO.sub.2 Me Hi-Pr N(CH.sub.3).sub.2 S Cl F CHMeCO.sub.2 Me Hi-Pr N(CH.sub.3).sub.2 S Cl Cl CHMeCO.sub.2 Me Hi-Pr N(CH.sub.3).sub.2 O Cl F CH(CH.sub.3)CH.sub.2i-Pr N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.3)CH.sub.2i-Pr N(CH.sub.3).sub.2 S Cl F CH(CH.sub.3)CH.sub.2i-Pr N(CH.sub.3).sub.2 S Cl Cl CH(CH.sub.3)CH.sub.2i-Pr CF.sub.3 O Cl F H Hi-Pr CF.sub.3 O Cl Cl H Hi-Pr CF.sub.3 S Cl F H Hi-Pr CF.sub.3 S Cl Cl H Hi-Pr CF.sub.3 O Cl F ##STR274## Hi-Pr CF.sub.3 O Cl Cl ##STR275## Hi-Pr CF.sub.3 S Cl F ##STR276## Hi-Pr CF.sub.3 S Cl Cl ##STR277## Hi-Pr CF.sub.3 O Cl F CH.sub.2 Ph Hi-Pr CF.sub.3 O Cl Cl CH.sub.2 Ph Hi-Pr CF.sub.3 S Cl F CH.sub.2 Ph Hi-Pr CF.sub.3 S Cl Cl CH.sub.2 Ph Hi-Pr CF.sub.3 O Cl F iPr Hi-Pr CF.sub.3 O Cl Cl iPr Hi-Pr CF.sub.3 S Cl F iPr Hi-Pr CF.sub.3 S Cl Cl iPr Hi-Pr CF.sub.3 O Cl F ##STR278## Hi-Pr CF.sub.3 O Cl Cl ##STR279## Hi-Pr CF.sub.3 S Cl F ##STR280## Hi-Pr CF.sub.3 S Cl Cl ##STR281## Hi-Pr CF.sub.3 O Cl F CH.sub.2 CHCH.sub.2 Hi-Pr CF.sub.3 O Cl Cl CH.sub.2 CHCH.sub.2 Hi-Pr CF.sub.3 S Cl F CH.sub.2 CHCH.sub.2 Hi-Pr CF.sub.3 S Cl Cl CH.sub.2 CHCH.sub.2 Hi-Pr CF.sub.3 O Cl F CHMeCO.sub.2 Me Hi-Pr CF.sub.3 O Cl Cl CHMeCO.sub.2 Me Hi-Pr CF.sub.3 S Cl F CHMeCO.sub.2 Me Hi-Pr CF.sub.3 S Cl Cl CHMeCO.sub.2 Me Hi-Pr CF.sub.3 O Cl F CH(CH.sub.3)CH.sub.2i-Pr CF.sub.3 O Cl Cl CH(CH.sub.3)CH.sub.2i-Pr CF.sub.3 S Cl F CH(CH.sub.3)CH.sub.2i-Pr CF.sub.3 S Cl Cl CH(CH.sub.3)CH.sub.2 ##STR282## N(CH.sub.3).sub.2 O Cl F H H ##STR283## N(CH.sub.3).sub.2 O Cl Cl H H ##STR284## N(CH.sub.3).sub.2 S Cl F H H ##STR285## N(CH.sub.3).sub.2 S Cl Cl H H ##STR286## N(CH.sub.3).sub.2 O Cl F ##STR287## H ##STR288## N(CH.sub.3).sub.2 O Cl Cl ##STR289## H ##STR290## N(CH.sub.3).sub.2 S Cl F ##STR291## H ##STR292## N(CH.sub.3).sub.2 S Cl Cl ##STR293## H ##STR294## N(CH.sub.3).sub.2 O Cl F CH.sub.2 Ph H ##STR295## N(CH.sub.3).sub.2 O Cl Cl CH.sub.2 Ph H ##STR296## N(CH.sub.3).sub.2 S Cl F CH.sub.2 Ph H ##STR297## N(CH.sub.3).sub.2 S Cl Cl CH.sub.2 Ph H ##STR298## N(CH.sub.3).sub.2 O Cl F iPr H ##STR299## N(CH.sub.3).sub.2 O Cl Cl iPr H ##STR300## N(CH.sub.3).sub.2 S Cl F iPr H ##STR301## N(CH.sub.3).sub.2 S Cl Cl iPr H ##STR302## N(CH.sub.3).sub.2 O Cl F ##STR303## H ##STR304## N(CH.sub.3).sub.2 O Cl Cl ##STR305## H ##STR306## N(CH.sub.3).sub.2 S Cl F ##STR307## H ##STR308## N(CH.sub.3).sub.2 S Cl Cl ##STR309## H ##STR310## N(CH.sub.3).sub.2 O Cl F CH.sub.2 CHCH.sub.2 H ##STR311## N(CH.sub.3).sub.2 O Cl Cl CH.sub.2 CHCH.sub.2 H ##STR312## N(CH.sub.3).sub.2 S Cl F CH.sub.2 CHCH.sub.2 H ##STR313## N(CH.sub.3).sub.2 S Cl Cl CH.sub.2 CHCH.sub.2 H ##STR314## N(CH.sub.3).sub.2 O Cl F CHMeCO.sub.2 Me H ##STR315## N(CH.sub.3).sub.2 O Cl Cl CHMeCO.sub.2 Me H ##STR316## N(CH.sub.3).sub.2 S Cl F CHMeCO.sub.2 Me H ##STR317## N(CH.sub.3).sub.2 S Cl Cl CHMeCO.sub.2 Me H ##STR318## N(CH.sub.3).sub.2 O Cl F CH(CH.sub.3)CH.sub.2 ##STR319## N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.3)CH.sub.2 ##STR320## N(CH.sub.3).sub.2 S Cl F CH(CH.sub.3)CH.sub.2 ##STR321## N(CH.sub.3).sub.2 S Cl Cl CH(CH.sub.3)CH.sub.2 ##STR322## CF.sub.3 O Cl F H H ##STR323## CF.sub.3 O Cl Cl H H ##STR324## CF.sub.3 S Cl F H H ##STR325## CF.sub.3 S Cl Cl H H ##STR326## CF.sub.3 O Cl F ##STR327## H ##STR328## CF.sub.3 O Cl Cl ##STR329## H ##STR330## CF.sub.3 S Cl F ##STR331## H ##STR332## CF.sub.3 S Cl Cl ##STR333## H ##STR334## CF.sub.3 O Cl F CH.sub.2 Ph H ##STR335## CF.sub.3 O Cl Cl CH.sub.2 Ph H ##STR336## CF.sub.3 S Cl F CH.sub.2 Ph H ##STR337## CF.sub.3 S Cl Cl CH.sub.2 Ph H ##STR338## CF.sub.3 O Cl F iPr H ##STR339## CF.sub.3 O Cl Cl iPr H ##STR340## CF.sub.3 S Cl F iPr H ##STR341## CF.sub.3 S Cl Cl iPr H ##STR342## CF.sub.3 O Cl F ##STR343## H ##STR344## CF.sub.3 O Cl Cl ##STR345## H ##STR346## CF.sub.3 S Cl F ##STR347## H ##STR348## CF.sub.3 S Cl Cl ##STR349## H ##STR350## CF.sub.3 O Cl F CH.sub.2 CHCH.sub.2 H ##STR351## CF.sub.3 O Cl Cl CH.sub.2 CHCH.sub.2 H ##STR352## CF.sub.3 S Cl F CH.sub.2 CHCH.sub.2 H ##STR353## CF.sub.3 S Cl Cl CH.sub.2 CHCH.sub.2 H ##STR354## CF.sub.3 O Cl F CHMeCO.sub.2 Me H ##STR355## CF.sub.3 O Cl Cl CHMeCO.sub.2 Me H ##STR356## CF.sub.3 S Cl F CHMeCO.sub.2 Me H ##STR357## CF.sub.3 S Cl Cl CHMeCO.sub.2 Me H ##STR358## CF.sub.3 O Cl F CH(CH.sub.3)CH.sub.2 ##STR359## CF.sub.3 O Cl Cl CH(CH.sub.3)CH.sub.2 ##STR360## CF.sub.3 S Cl F CH(CH.sub.3)CH.sub.2 ##STR361## CF.sub.3 S Cl Cl CH(CH.sub.3)CH.sub.2CHO CF.sub.3 O Cl F ##STR362## HCHO CF.sub.3 O Cl Cl ##STR363## HCHO CF.sub.3 O Cl F CH(CH.sub.3)CH.sub.2CHO CF.sub.3 O Cl Cl CH(CH.sub.3)CH.sub.2COCH.sub.3 CF.sub.3 O Cl F ##STR364## HCOCH.sub.3 CF.sub.3 O Cl Cl ##STR365## HCOCH.sub.3 CF.sub.3 O Cl F CH(CH.sub.3)CH.sub.2COCH.sub.3 CF.sub.3 O Cl Cl CH(CH.sub.3)CH.sub.2COCH.sub.3 N(CH.sub.3).sub.2 O Cl F ##STR366## HCOCH.sub.3 N(CH.sub.3).sub.2 O Cl Cl ##STR367## HCOCH.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CH.sub.3)CH.sub.2COCH.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.3)CH.sub.2CHF.sub.2 CF.sub.3 O Cl F ##STR368## HCHF.sub.2 CF.sub.3 O Cl Cl ##STR369## HCHF.sub.2 CF.sub.3 O Cl F CH(CH.sub.3)CH.sub.2CHF.sub.2 CF.sub.3 O Cl Cl CH(CH.sub.3)CH.sub.2CHF.sub.2 N(CH.sub.3).sub.2 O Cl F ##STR370## HCHF.sub.2 N(CH.sub.3).sub.2 O Cl Cl ##STR371## HCHF.sub.2 N(CH.sub.3).sub.2 O Cl F CH(CH.sub.3)CH.sub.2CHF.sub.2 N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.3)CH.sub.2CH.sub.2 F CF.sub.3 O Cl F ##STR372## HCH.sub.2 F CF.sub.3 O Cl Cl ##STR373## HCH.sub.2 F CF.sub.3 O Cl F CH(CH.sub.3)CH.sub.2CH.sub.2 F CF.sub.3 O Cl Cl CH(CH.sub.3)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl F ##STR374## HCH.sub.2 F N(CH.sub.3).sub.2 O Cl Cl ##STR375## HCH.sub.2 F N(CH.sub.3).sub.2 O Cl F CH(CH.sub.3)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.3)CH.sub.2 ##STR376## N(CH.sub.3).sub.2 O Cl F ##STR377## H ##STR378## N(CH.sub.3).sub.2 O Cl Cl ##STR379## H ##STR380## N(CH.sub.3).sub.2 O Cl F CH(CH.sub.3)CH.sub.2 ##STR381## N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.3)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CF.sub.3)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CF.sub.3)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CF.sub.3)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CF.sub.3)CH.sub.2CH.sub.3 CF.sub.3 O Cl F CH(CF.sub.3)CH.sub.2CH.sub.3 CF.sub.3 O Cl Cl CH(CF.sub.3)CH.sub.2CH.sub.3 CF.sub.3 S Cl F CH(CF.sub.3)CH.sub.2CH.sub.3 CF.sub.3 S Cl Cl CH(CF.sub.3)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CF.sub.3)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CF.sub.3)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CF.sub.3)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CF.sub.3)CH.sub.2CF.sub.3 CF.sub.3 O Cl F CH(CF.sub.3)CH.sub.2CF.sub.3 CF.sub.3 O Cl Cl CH(CF.sub.3)CH.sub.2CF.sub.3 CF.sub.3 S Cl F CH(CF.sub.3)CH.sub.2CF.sub.3 CF.sub.3 S Cl Cl CH(CF.sub.3)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl F CH(CF.sub.3)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl Cl CH(CF.sub.3)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 S Cl F CH(CF.sub.3)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 S Cl Cl CH(CF.sub.3)CH.sub.2CH.sub.2 F CF.sub.3 O Cl F CH(CF.sub.3)CH.sub.2CH.sub.2 F CF.sub.3 O Cl Cl CH(CF.sub.3)CH.sub.2CH.sub.2 F CF.sub.3 S Cl F CH(CF.sub.3)CH.sub.2CH.sub.2 F CF.sub.3 S Cl Cl CH(CF.sub.3)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CHCH.sub.2)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CHCH.sub.2)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CHCH.sub.2)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CHCH.sub.2)CH.sub.2CH.sub.3 CF.sub.3 O Cl F CH(CHCH.sub.2)CH.sub.2CH.sub.3 CF.sub.3 O Cl Cl CH(CHCH.sub.2)CH.sub.2CH.sub.3 CF.sub.3 S Cl F CH(CHCH.sub.2)CH.sub.2CH.sub.3 CF.sub.3 S Cl Cl CH(CHCH.sub.2)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CHCH.sub.2)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CHCH.sub.2)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CHCH.sub.2)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CHCH.sub.2)CH.sub.2CF.sub.3 CF.sub.3 O Cl F CH(CHCH.sub.2)CH.sub.2CF.sub.3 CF.sub.3 O Cl Cl CH(CHCH.sub.2)CH.sub.2CF.sub.3 CF.sub.3 S Cl F CH(CHCH.sub.2)CH.sub.2CF.sub.3 CF.sub.3 S Cl Cl CH(CHCH.sub.2)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl F CH(CHCH.sub.2)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl Cl CH(CHCH.sub.2)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 S Cl F CH(CHCH.sub.2)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 S Cl Cl CH(CHCH.sub.2)CH.sub.2CH.sub.2 F CF.sub.3 O Cl F CH(CHCH.sub.2)CH.sub.2CH.sub.2 F CF.sub.3 O Cl Cl CH(CHCH.sub.2)CH.sub.2CH.sub.2 F CF.sub.3 S Cl F CH(CHCH.sub.2)CH.sub.2CH.sub.2 F CF.sub.3 S Cl Cl CH(CHCH.sub.2)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 O Cl F ##STR382##CH.sub.3 N(CH.sub.3).sub.2 O Cl Cl ##STR383##CH.sub.3 N(CH.sub.3).sub.2 S Cl F ##STR384##CH.sub.3 N(CH.sub.3).sub.2 S Cl Cl ##STR385##CH.sub.3 CF.sub.3 O Cl F ##STR386##CH.sub.3 CF.sub.3 O Cl Cl ##STR387##CH.sub.3 CF.sub.3 S Cl F ##STR388##CH.sub.3 CF.sub.3 S Cl Cl ##STR389##CF.sub.3 N(CH.sub.3).sub.2 O Cl F ##STR390##CF.sub.3 N(CH.sub.3).sub.2 O Cl Cl ##STR391##CF.sub.3 N(CH.sub.3).sub.2 S Cl F ##STR392##CF.sub.3 N(CH.sub.3).sub.2 S Cl Cl ##STR393##CF.sub.3 CF.sub.3 O Cl F ##STR394##CF.sub.3 CF.sub.3 O Cl Cl ##STR395##CF.sub.3 CF.sub.3 S Cl F ##STR396##CF.sub.3 CF.sub.3 S Cl Cl ##STR397##CH.sub.2 F N(CH.sub.3).sub.2 O Cl F ##STR398##CH.sub.2 F N(CH.sub.3).sub.2 O Cl Cl ##STR399##CH.sub.2 F N(CH.sub.3).sub.2 S Cl F ##STR400##CH.sub.2 F N(CH.sub.3).sub.2 S Cl Cl ##STR401##CH.sub.2 F CF.sub.3 O Cl F ##STR402##CH.sub.2 F CF.sub.3 O Cl Cl ##STR403##CH.sub.2 F CF.sub.3 S Cl F ##STR404##CH.sub.2 F CF.sub.3 S Cl Cl ##STR405##CH.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.3 CF.sub.3 O Cl F CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.3 CF.sub.3 O Cl Cl CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.3 CF.sub.3 S Cl F CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.3 CF.sub.3 S Cl Cl CH(CH.sub.2 CH.sub.3)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CH.sub.2 CH.sub.3)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.2 CH.sub.3)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CH.sub.2 CH.sub.3)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CH.sub.2 CH.sub.3)CH.sub.2CF.sub.3 CF.sub.3 O Cl F CH(CH.sub.2 CH.sub.3)CH.sub.2CF.sub.3 CF.sub.3 O Cl Cl CH(CH.sub.2 CH.sub.3)CH.sub.2CF.sub.3 CF.sub.3 S Cl F CH(CH.sub.2 CH.sub.3)CH.sub.2CF.sub.3 CF.sub.3 S Cl Cl CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl F CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 S Cl F CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 S Cl Cl CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.2 F CF.sub.3 O Cl F CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.2 F CF.sub.3 O Cl Cl CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.2 F CF.sub.3 S Cl F CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.2 F CF.sub.3 S Cl Cl CH(CH.sub.2 CH.sub.3)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CH.sub.2 F)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.2 F)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CH.sub.2 F)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CH.sub.2 F)CH.sub.2CH.sub.3 CF.sub.3 O Cl F CH(CH.sub.2 F)CH.sub.2CH.sub.3 CF.sub.3 O Cl Cl CH(CH.sub.2 F)CH.sub.2CH.sub.3 CF.sub.3 S Cl F CH(CH.sub.2 F)CH.sub.2CH.sub.3 CF.sub.3 S Cl Cl CH(CH.sub.2 F)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CH.sub.2 F)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.2 F)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CH.sub.2 F)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CH.sub.2 F)CH.sub.2CF.sub.3 CF.sub.3 O Cl F CH(CH.sub.2 F)CH.sub.2CF.sub.3 CF.sub.3 O Cl Cl CH(CH.sub.2 F)CH.sub.2CF.sub.3 CF.sub.3 S Cl F CH(CH.sub.2 F)CH.sub.2CF.sub.3 CF.sub.3 S Cl Cl CH(CH.sub.2 F)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl F CH(CH.sub.2 F)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl Cl CH(CH.sub.2 F)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 S Cl F CH(CH.sub.2 F)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 S Cl Cl CH(CH.sub.2 F)CH.sub.2CH.sub.2 F CF.sub.3 O Cl F CH(CH.sub.2 F)CH.sub.2CH.sub.2 F CF.sub.3 O Cl Cl CH(CH.sub.2 F)CH.sub.2CH.sub.2 F CF.sub.3 S Cl F CH(CH.sub.2 F)CH.sub.2CH.sub.2 F CF.sub.3 S Cl Cl CH(CH.sub.2 F)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CN)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CN)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CN)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CN)CH.sub.2CH.sub.3 CF.sub.3 O Cl F CH(CN)CH.sub.2CH.sub.3 CF.sub.3 O Cl Cl CH(CN)CH.sub.2CH.sub.3 CF.sub.3 S Cl F CH(CN)CH.sub.2CH.sub.3 CF.sub.3 S Cl Cl CH(CN)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CN)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CN)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CN)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CN)CH.sub.2CF.sub.3 CF.sub.3 O Cl F CH(CN)CH.sub.2CF.sub.3 CF.sub.3 O Cl Cl CH(CN)CH.sub.2CF.sub.3 CF.sub.3 S Cl F CH(CN)CH.sub.2CF.sub.3 CF.sub.3 S Cl Cl CH(CN)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl F CH(CN)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl Cl CH(CN)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 S Cl F CH(CN)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 S Cl Cl CH(CN)CH.sub.2CH.sub.2 F CF.sub.3 O Cl F CH(CN)CH.sub.2CH.sub.2 F CF.sub.3 O Cl Cl CH(CN)CH.sub.2CH.sub.2 F CF.sub.3 S Cl F CH(CN)CH.sub.2CH.sub.2 F CF.sub.3 S Cl Cl CH(CN)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CF.sub.2 H)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CF.sub.2 H)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CF.sub.2 H)CH.sub.2CH.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CF.sub.2 H)CH.sub.2CH.sub.3 CF.sub.3 O Cl F CH(CF.sub.2 H)CH.sub.2CH.sub.3 CF.sub.3 O Cl Cl CH(CF.sub.2 H)CH.sub.2CH.sub.3 CF.sub.3 S Cl F CH(CF.sub.2 H)CH.sub.2CH.sub.3 CF.sub.3 S Cl Cl CH(CF.sub.2 H)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl F CH(CF.sub.2 H)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 O Cl Cl CH(CF.sub.2 H)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl F CH(CF.sub.2 H)CH.sub.2CF.sub.3 N(CH.sub.3).sub.2 S Cl Cl CH(CF.sub.2 H)CH.sub.2CF.sub.3 CF.sub.3 O Cl F CH(CF.sub.2 H)CH.sub.2CF.sub.3 CF.sub.3 O Cl Cl CH(CF.sub.2 H)CH.sub.2CF.sub.3 CF.sub.3 S Cl F CH(CF.sub.2 H)CH.sub.2CF.sub.3 CF.sub.3 S Cl Cl CH(CF.sub.2 H)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl F CH(CF.sub.2 H)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 O Cl Cl CH(CF.sub.2 H)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 S Cl F CH(CF.sub.2 H)CH.sub.2CH.sub.2 F N(CH.sub.3).sub.2 S Cl Cl CH(CF.sub.2 H)CH.sub.2CH.sub.2 F CF.sub.3 O Cl F CH(CF.sub.2 H)CH.sub.2CH.sub.2 F CF.sub.3 O Cl Cl CH(CF.sub.2 H)CH.sub.2CH.sub.2 F CF.sub.3 S Cl F CH(CF.sub.2 H)CH.sub.2CH.sub.2 F CF.sub.3 S Cl Cl CH(CF.sub.2 H)CH.sub.2______________________________________
FORMULATION
Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent. Use formulations include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like, consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up 100 weight percent.
______________________________________ Weight Percent Active Ingredient Diluent Surfactant______________________________________Wettable Powders 25-90 0-74 1-10Oil Suspensions, 5-50 40-95 0-15Emulsions, Solutions,(including EmulsifiableConcentrates)Dusts 1-25 70-99 0-5Granules and Pellets 0.01-99 5-99.99 0-15High Strength 90-99 0-10 0-2Compositions______________________________________
Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J. Typical liquid diluents and solvents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J., as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.
Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill. Water-dispersible granules can be produced be agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations, Washington, D.C., 1988, pp 251-259. Suspensions are prepared by wet-milling; see, for example, U.S. Pat. No. 3,060,084. Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can also be prepared as taught in DE 3,246,493.
For further information regarding the art of formulation, see U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989.
In the following Examples, all percentages are by weight and all formulations are worked up in conventional ways. Compound numbers refer to compounds in Table IV.
______________________________________Example AHigh Strength ConcentrateCompound 1 98.5%silica aerogel 0.5%synthetic amorphous fine silica 1.0%Example BWettable PowderCompound 1 65.0%dodecylphenol polyethylene glycol ether 2.0%sodium ligninsulfonate 4.0%sodium silicoaluminate 6.0%montmorillonite (calcined) 23.0%Example CGranuleCompound 1 10.0%attapulgite granules (low volative 90.0%matter, 0.71/0.30 mm; U.S.S. No.25-50 sieves)Example DExtruded PelletCompound 1 25.0%anhydrous sodium sulfate 10.0%crude calcium ligninsulufonate 5.0%sodium alkylnaphthalenesulfonate 1.0%calcium/magnesium bentonite 59.0%______________________________________
UTILITY
The compounds of the present invention are active postemergence and preemergence herbicides and especially for broadleaf and grass weed control in plantation crops including citrus, sugarcane, coffee, oil palm, rubber, pineapple, grapes, banana and conifers, such as loblolly pine. Most of the plantation crops are very important in mankind's diet while others are sources of useful raw materials. The compounds can be applied as preemergence or postemergence treatments using techniques of banding, directed sprays or broadcast applications. By selecting effective application rates, application techniques and adjuvants, compounds of this invention can be used for selective weed control in plantation crops.
Alternatively, compounds of this invention can be used in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil well sites, drive-in theaters, around billboards, highways and railroad structures and in fence rows.
Effective application rates for the compounds of this invention are 5 to 5000 g/ha with a preferred rate range of 10 to 2000 g/ha. One skilled in the art can select the effective rates for a given situation.
The compounds of this invention may be used alone or in combination with other commercial herbicides, insecticides or fungicides. The following list exemplifies some of the herbicides suitable for use in mixtures. A combination of a compound from this invention with one or more of the following herbicides may be particularly useful for weed control in plantation crops.
Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control. Examples of other herbicides with which compounds of this invention can be formulated are: acetochlor, acifluorfen, acrolein, 2-propenal, alachlor, ametryn, amidosulfuron, ammonium sulfamate, amitrole, anilofos, asulam, atrazine, barban, benefin, bensulfuron methyl, bensulide, bentazon, benzofluor, benzoylprop, bifenox, bromacil, bromoxynil, bromoxynil heptanoate, bromoxynil octanoate, butachlor, buthidazole, butralin, butylate, cacodylic acid, 2-chloro-N,N-di-2-propenylacetamide, 2-chloroallyl diethyldithiocarbamate, chloramben, chlorbromuron, chloridazon, chlorimuron ethyl, chlormethoxynil, chlornitrofen, chloroxuron, chlorpropham, chlorsulfuron, chlortoluron, cinmethylin, cinosulfuron, clethodim, clomazone, cloproxydim, clopyralid, calcium salt of methylarsonic acid, cyanazine, cycloate, cycluron, cyperquat, cyprazine, cyprazole, cypromid, dalapon, dazomet, dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate, desmedipham, desmetryn, dicamba, dichlobenil, dichlorprop, diclofop, diethatyl, difenzoquat, diflufenican, dimepiperate, dinitramine, dinoseb, diphenamid, dipropetryn, diquat, diuron, 2-methyl-4,6-dinitrophenol, disodium salt of methylarsonic acid, dymron, endothall, S-ethyl dipropylcarbamothioate, esprocarb, ethalfluralin, ethametsulfuron methyl, ethofumesate, fenac, fenoxaprop, fenuron, salt of fenuron and trichloroacetic acid, flamprop, fluazifop, fluazifop-P, fluchloralin, flumesulam, flumipropyn, fluometuron, fluorochloridone, fluorodifen, fluoroglycofen, flupoxam, fluridone, fluroxypyr, fluzasulfuron, fomesafen, fosamine, glyphosate, haloxyfop, hexaflurate, hexazinone, imazamethabenz, imazapyr, imazaquin, imazamethabenz methyl, imazethapyr, imazosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, karbutilate, lactofen, lenacil, linuron, metobenzuron, metsulfuron methyl, methylarsonic acid, monoammonium salt of methylarsonic acid, (4-chloro-2-methylphenoxy)acetic acid, S,S'-dimethyl-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarbothioate, mecoprop, mefenacet, mefluidide, methalpropalin, methabenzthiazuron, metham, methazole, methoxuron, metolachlor, metribuzin, 1,2-dihydropyridazine-3,6-dione, molinate, monolinuron, monuron, monuron salt and trichloroacetic acid, monosodium salt of methylarsonic acid, napropamide, naptalam, neburon, nicosulfuron, nitralin, nitrofen, nitrofluorfen, norea, norflurazon, oryzalin, oxadiazon, oxyfluorfen, paraquat, pebulate, pendimethalin, perfluidone, phenmedipham, picloram, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitroacetophenone oxime-O-acetic acid methyl ester, pretilachlor, primisulfuron, procyazine, profluralin, prometon, prometryn, pronamide, propachlor, propanil, propazine, propham, prosulfalin, prynachlor, pyrazolate, pyrazon, pyrazosulfuron ethyl, quinchlorac, quizalofop ethyl, rimsulfuron, secbumeton, sethoxydim, siduron, simazine, 1-(a,a-dimethylbenzyl)-3-(4-methylphenyl)urea, sulfometuron methyl, trichloroacetic acid, tebuthiuron, terbacil, terbuchlor, terbuthylazine, terbutol, terbutryn, thifensulfuron methyl, thiobencarb, triallate, trialkoxydim, triasulfuron, tribenuron methyl, triclopyr, tridiphane, trifluralin, trimeturon, (2,4-dichlorophenoxy)acetic acid, 4-(2,4-dichlorophenoxy)butanoic acid, vernolate, and xylachlor.
In certain instances, combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management.
A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of a compound(s) of this invention is applied at rates from about 0.001 to 20 kg/ha with a preferred rate range of 0.004 to 0.25 kg/ha. One skilled in the art can easily determine application rates necessary for the desired level of weed control.
The following Tests demonstrate the control efficacy of the compounds of this invention specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables IV through VI for compound descriptions.
Selective herbicidal properties of the subject compounds were discovered in greenhouse tests as described below. Test procedures and results follows.
TABLE IV__________________________________________________________________________ ##STR406## m.p.No. R.sup.1 R.sup.2 R.sup.3 X Y (.degree.C.) .sup.1 H-NMR__________________________________________________________________________1 CH.sub.3 CH.sub.2 Ph CF.sub.3 Cl F 145-147 7.4 (m, 6H) 6.85 (d, 1H) 6.4 (s, 1H) 5.1 (s, 2H) 3.55 (s, 3H)2 CH.sub.3 H CF.sub.3 Cl F Foam 7.15 (d, 1H) 6.9 (d, 1H) 6.4 (s, 1H) 5.8 (s, 1H) 3.6 (s, 3H)3 CH.sub.3 ##STR407## CF.sub.3 Cl F Foam ##STR408## ##STR409## ##STR410## CF.sub.3 Cl F Oil ##STR411##7 CH.sub.2 CHCH.sub.2 CH.sub.2 CHCH.sub.2 CF.sub.3 Cl F Oil 7.3 (d, 1H) 6.8 (d, 1H) 6.4 (s, 1H) 6.0 (m, 2H) 5.4 (m, 4H) 4.6 (d, 4H)9 CH.sub.3 CH.sub.2 CHCH.sub.2 CF.sub.3 Cl F 102-105 7.3 (d, 1H) 6.8 (d, 1H) 6.4 (s, 1H) 6.0 (m, 1H) 5.4 (m, 2H) 4.6 (d, 2H) 3.6 (s, 3H)__________________________________________________________________________
TABLE V__________________________________________________________________________ ##STR412##No. R.sup.1 R.sup.3 R.sup.4 R.sup.9 X Y m.p. (.degree.C.) .sup.1 H-NMR__________________________________________________________________________11 CH.sub.3 CF.sub.3 H CH.sub.3 Cl F Foam 7.05 (d, 1H) 6.4 (s, 1H) 5.1 (m, 1H) 3.55 (s, 3H) 3.1 (m, 1H) 2.8 (m, 1H) 1.5 (d, 3H)12 CH.sub.3 CF.sub.3 H CH.sub.3 Cl Cl 64-66 7.3 (s, 1H) 6.4 (s, 1H) 5.1 (m, 1H) 3.6 (d, 3H) 3.25 (m, 1H) 2.75 (m, 1H) 1.54 (d, d 3H)13 ##STR413## CF.sub.3 H CH.sub.3 Cl F Oil ##STR414##14 CH.sub.2 CH.sub.2 CH.sub.2 CF.sub.3 H CH.sub.3 Cl F Oil 7.05 (d, 1H) 6.4 (s, 1H) 5.9 (m, 1H) 5.3 (m, 2H) 5.1 (m, 1H) 4.6 (d, 1H) 3.2 (m, 1H) 2.8 (m, 1H) 1.5 (d, 3H)15 CH.sub.2 Ph CF.sub.3 H CH.sub.3 Cl F Oil 7.2 (m, 7H) 7.0 (d, 1H) 6.4 (s, 1H) 5.2 (d, 2H) 5.1 (m, 1H) 3.1 (m, 1H) 2.7 (m, 1H) 1.5 (d, 3H)17 CH.sub.3 CH.sub.3 H CH.sub.3 Cl F Oil 7.0 (d, 1H) 5.7 (s, 1H) 5.0 (m, 1H) 3.4 (s, 3H) 3.2 (d, d 1H) 2.8 (d, d 1H) 2.3 (s, 3H) 1.5 (d, 3H)19 CH.sub.2 CH.sub.3 CH.sub.3 H CH.sub.3 Cl F 140-142 7.0 (d, 1H) 5.68 (s, 1H) 5.05 (m, 1H) 3.95 (q, 1H) 3.2 (qu, 1H) 2.8 (qu, 1H) 2.35 (s, 3H) 1.55 (d, 3H) 1.3 (t, 3H)20 CH.sub.3 CF.sub.3 H CO.sub.2 H Cl F 190-19421 CH.sub.3 CF.sub.3 H CO.sub.2 tBu Cl F 65-6722 CH.sub.3 CF.sub.3 H CO.sub.2 CH.sub.3 Cl F 77-7923 CH.sub.3 CF.sub.3 H CO.sub.2 iPr Cl F 56-5924 CH.sub.3 CF.sub.3 H CON(CH.sub.3).sub.2 Cl F 92-9425 CH.sub.3 CF.sub.3 H CH.sub.2 OC(O)CH.sub.3 Cl F 58-61__________________________________________________________________________
TABLE VI__________________________________________________________________________ ##STR415##No. R.sup.1 R.sup.3 X Y R.sup.2 m.p. (.degree.C.) .sup.1 H-NMR__________________________________________________________________________5 CH.sub.3 N(CH.sub.3).sub.2 Cl F H 247-249 7.45 (d, 1H) 6.95 (d, 1H) 3.3 (s, 3H) 3.0 (s, 6H)6 CH.sub.3 N(CH.sub.3).sub.2 Cl F CH.sub.2 Ph 193-194 7.4 (m, 6H) 6.95 (d, 1H) 5.05 (d, 2H) 3.45 (s, 3H) 3.1 (s, 6H)8 CH.sub.3 N(CH.sub.3).sub.2 Cl F ##STR416## 61-65 ##STR417##16 CH.sub.3 N(CH.sub.3).sub.2 Cl F H 134-135 7.28 (s, 1H) 6.84 (d, 1H) 6.05 (m, 1H) 5.45 (d, 1H) 5.3 (d, 1H) 4.55 (s, 2H) 3.45 (s, 3H) 3.12 (s, 6H)18 CH.sub.3 N(CH.sub.3).sub.2 Cl F CH(CH.sub.3)CH.sub.2 191-195 7.3 (d, 1H) 6.8 (d, 1H) 6.36 (s, 1H) 6.0 (m, 1H) 5.4 (m, 2H) 4.55 (d, 2H) 3.56 (s, 3H)__________________________________________________________________________
TEST A
Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), cheatgrass (Bromus secalinus), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays, cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response indicates no test result.
TABLE A______________________________________ COMPOUNDRate 400 g/ha 1 2 3 5 6 8 11 16 17 18______________________________________POSTEMERGENCEBarley 6 9 10 3 4 5 10 -- 6 8Barnyardgrass 9 10 10 5 3 10 10 7 9 10Bedstraw 10 10 10 3 4 8 10 -- 8 10Blackgrass 10 9 10 3 4 5 10 -- 5 9Cheatgrass 7 8 10 4 4 5 10 -- 5 10Chickweed 10 10 10 3 4 8 10 -- 5 10Cocklebur 10 10 10 3 6 8 10 8 7 9Corn 6 9 10 2 3 10 10 3 6 9Cotton 10 10 10 9 9 10 10 10 10 10Crabgrass 5 7 10 3 4 10 10 5 9 9Giant foxtail 8 10 10 3 6 9 10 9 9 10Lambsquarter 10 10 10 5 8 10 10 -- 10 10Morningglory 10 10 10 8 7 9 10 10 9 10Nutsedge 5 -- -- 1 0 9 7 2 2 5Rape 10 7 10 1 5 9 10 -- 7 10Rice 6 7 10 3 3 9 10 7 9 9Sorghum 6 9 10 2 3 6 10 4 9 10Soybean 10 10 10 4 6 9 10 9 9 9Sugar beet 10 10 10 5 9 10 10 -- 10 10Velvetleaf 10 10 10 2 9 10 10 10 10 10Wheat 5 -- -- 3 4 6 10 -- 7 10Wild buckwheat -- -- -- 6 6 10 10 -- 10 10Wild oat 9 9 10 2 4 6 10 -- 8 10PREEMERGENCEBarley 3 3 9 0 0 8 9 -- 4 5Barnyardgrass 9 9 10 0 0 9 10 9 10 10Bedstraw 10 10 10 3 10 10 10 -- 10 9Blackgrass 10 7 10 0 5 9 10 -- 4 10Cheatgrass 10 10 10 0 0 9 10 -- 9 10Chickweed 10 9 10 0 3 10 10 -- 4 9Cocklebur 0 7 10 0 0 10 10 6 6 10Corn 3 4 10 0 0 6 10 8 8 10Cotton 8 8 10 0 0 10 10 6 8 10Crabgrass 10 9 10 0 9 10 10 10 10 10Giant foxtail 10 10 10 0 9 10 10 10 10 10Lambsquarter 10 10 10 0 10 10 10 -- 10 10Morningglory 5 10 10 0 0 10 10 10 9 10Nutsedge 2 10 10 0 10 1 7 3 4 5Rape 10 10 10 1 2 10 10 -- 10 10Rice 5 3 10 0 0 10 10 6 9 10Sorghum 7 9 10 0 0 4 10 8 9 10Soybean 3 9 10 0 0 6 10 4 9 9Sugar beet 10 10 10 1 9 10 10 -- 10 10Velvetleaf 10 10 10 0 10 10 10 10 10 10Wheat 3 7 10 0 0 9 9 -- 6 8Wild buckwheat 10 10 10 0 10 10 10 -- 10 10Wild oat 9 9 10 0 0 10 10 -- 3 10______________________________________ COMPOUNDRate 200 g/ha 4 9 12______________________________________POSTEMERGENCEBarley 5 7 7Barnyardgrass 10 10 6Bedstraw 9 10 9Blackgrass 6 9 4Cheatgrass 7 9 5Chickweed 10 10 6Cocklebur 7 10 7Corn 9 9 7Cotton 10 10 10Crabgrass 9 10 7Giant foxtail 9 10 8Lambsquarter 10 10 10Morningglory 9 10 9Nutsedge 5 5 1Rape 10 10 9Rice 10 9 9Sorghum 9 9 9Soybean 9 9 10Sugar beet 10 10 10Velvetleaf 10 10 8Wheat 7 6 7Wild buckwheat 10 10 10Wild oat 9 10 8PREEMERGENCEBarley 2 6 1Barnyardgrass 10 10 9Bedstraw 9 10 10Blackgrass 9 10 8Cheatgrass 9 10 3Chickweed 10 10 1Cocklebur 6 10 7Corn 9 9 9Cotton 7 9 3Crabgrass 10 10 10Giant foxtail 10 10 10Lambsquarter 10 10 10Morningglory 10 10 10Nutsedge 10 2 0Rape 8 10 10Rice 9 9 8Sorghum 9 10 7Soybean 9 10 8Sugar beet 9 10 10Velvetleaf 10 10 10Wheat 7 9 2Wild buckwheat 10 10 10Wild oat 8 10 6______________________________________ COMPOUNDRate 100 g/ha 1 2 3 5 6 8 11 16 17 18______________________________________POSTEMERGENCEBarley 5 5 7 3 3 5 7 -- 4 7Barnyardgrass 8 7 10 1 2 4 10 3 8 9Bedstraw 8 9 10 2 3 5 10 -- 7 9Blackgrass 6 5 10 2 2 5 10 -- 4 6Cheatgrass 6 5 9 1 3 4 10 -- 3 5Chickweed -- -- 10 2 2 6 10 -- 4 8Cocklebur 8 6 10 2 4 6 10 7 6 8Corn 5 3 9 2 2 7 9 3 4 6Cotton 10 10 10 9 10 10 10 10 10 10Crabgrass 4 2 10 2 -- 7 10 2 5 8Giant foxtail 5 9 10 2 5 7 10 4 7 8Lambsquarter 10 10 10 3 7 9 10 -- 10 10Morningglory 10 10 10 5 7 9 10 8 8 10Nutsedge 5 2 -- 0 0 -- 8 0 2 3Rape 10 3 10 1 2 7 10 -- 5 9Rice 5 6 9 3 3 6 10 4 9 8Sorghum 5 4 9 1 2 5 10 4 5 8Soybean 8 8 10 3 5 8 9 8 9 9Sugar beet 10 10 10 3 7 10 10 -- 9 10Velvetleaf 10 10 10 2 6 7 10 10 9 10Wheat 4 4 9 3 2 4 8 -- 5 9Wild buckwheat -- -- 10 3 3 10 10 -- 9 9Wild oat 7 5 9 3 3 4 9 -- 6 9PREEMERGENCEBarley 0 0 4 0 0 1 8 -- 0 2Barnyardgrass 8 3 10 0 0 3 10 2 8 9Bedstraw 10 5 10 0 0 2 10 -- 4 8Blackgrass 9 3 10 0 0 5 10 -- 2 6Cheatgrass 5 2 8 0 0 4 10 -- 1 8Chickweed 10 -- 10 0 2 5 10 -- 2 9Cocklebur 0 0 10 0 0 2 10 2 2 5Corn 3 0 9 0 0 0 9 1 2 7Cotton 0 0 10 0 0 1 10 2 4 10Crabgrass 9 6 10 0 9 10 10 2 9 9Giant foxtail 9 10 10 0 0 2 10 5 5 10Lambsquarter 10 10 10 0 10 10 10 -- 10 9Morningglory 0 2 10 0 0 3 10 6 4 10Nutsedge 0 8 7 0 0 0 5 2 1 4Rape 10 3 10 0 0 9 10 -- 6 9Rice 1 1 9 0 0 6 9 3 4 8Sorghum 3 1 9 0 0 3 10 1 1 6Soybean 1 2 9 0 0 2 10 1 8 5Sugar beet 5 7 10 0 0 7 10 -- 9 9Velvetleaf 2 10 10 0 0 10 10 6 10 10Wheat 0 1 8 0 0 1 7 -- 0 4Wild buckwheat 10 0 10 0 0 8 10 -- 10 9Wild oat 7 3 9 0 0 0 9 -- 0 5______________________________________ COMPOUNDRate 50 g/ha 4 9 12______________________________________POSTEMERGENCEBarley 4 5 5Barnyardgrass 7 9 4Bedstraw 9 10 6Blackgrass 4 6 2Cheatgrass 5 6 3Chickweed 10 10 3Cocklebur 6 10 4Corn 5 7 4Cotton 9 10 9Crabgrass 6 9 5Giant foxtail 7 9 7Lambsquarter 10 10 9Morningglory 8 10 6Nutsedge 5 3 1Rape 10 10 5Rice 8 8 7Sorghum 7 8 5Soybean 9 9 6Sugar beet 10 10 9Velvetleaf 8 10 5Wheat 5 7 3Wild buckwheat 10 10 9Wild oat 5 7 4PREEMERGENCEBarley 0 2 0Barnyardgrass 7 9 7Bedstraw 10 10 8Blackgrass 5 9 5Cheatgrass 5 8 2Chickweed 10 10 0Cocklebur 0 9 0Corn 5 9 6Cotton 2 7 2Crabgrass 9 10 10Giant foxtail 8 10 9Lambsquarter 10 10 10Morningglory 2 10 5Nutsedge 5 3 0Rape 2 10 7Rice 2 9 7Sorghum 3 9 6Soybean 2 10 5Sugar beet 9 10 10Velvetleaf 9 10 9Wheat 0 7 1Wild buckwheat 9 10 5Wild oat 5 8 1______________________________________
TEST B
The compounds evaluated in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (flood application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood test. Water depth was approximately 2.5 cm for the flood test and was maintained at this level for the duration of the test.
Plant species in the preemergence and postemergence tests consisted of barley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthusretroflexus), rape (Brassica napus), ryegrass (Lolium multiflorum), sorghum (Sorghum bicolor), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua).
All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the post-emergence portion of the test. Plant species in the flood test consisted of barnyardgrass (Echinochloa crus-galli), rice (Oryza sativa), umbrella sedge (Cyperus difformis) and duck salad (Heteranthera limosa). All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty one days after application of the test compound. Plant response ratings, summarized in Table B, were recorded on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response indicates no test result.
TABLE B______________________________________ COMPOUNDRate 250 g/ha 4______________________________________POSTEMERGENCEBarley Igri 70Barnyard 2 leaf --Barnyardgrass 100Bedstraw 100Blackgrass 100Chickweed 100Corn 90Cotton 100Crabgrass 100Downy Brome 100Duck salad 15Giant foxtail 100Lambsquarters 100Morningglory 100Pigweed 100Rape 100Rice Japonica 100Ryegrass 90Sorghum 100Soybean 100Speedwell --Sugar beet 100Umbrella sedge 10Velvetleaf 100Wheat 90Wild buckwheat 100Wild oat 90PREEMERGENCEBarley Igri 50Bedstraw 100Blackgrass 100Chickweed 100Corn 100Cotton 100Crabgrass 100Downy Brome 95Giant foxtail 100Lambsquarters 10)Morningglory 100Pigweed 100Rape 100Ryegrass 100Sorghum 100Soybean 100Speedwell --Sugar beet 100Velvetleaf 100Wheat 90Wild buckwheat 100Wild oat 95______________________________________ COMPOUNDRate 125 g/ha 1 3 4 9 12______________________________________POSTEMERGENCEBarley Igri 0 100 60 95 --Barnyard 2 leaf -- -- -- -- --Barnyardgrass 100 100 100 100 100Bedstraw 100 100 100 100 --Blackgrass 50 100 100 100 --Chickweed 100 100 100 100 --Corn 25 98 90 98 --Cotton 100 100 100 100 --Crabgrass 50 100 95 100 --Downy Brome 0 100 85 100 --Duck salad 0 90 0 95 30Giant foxtail 100 100 100 100 --Lambsquarters 100 100 100 100 --Morningglory 100 100 100 100 --Pigweed 100 100 100 100 --Rape 100 100 100 100 --Rice Japonica 95 100 100 100 95Ryegrass 40 100 70 100 --Sorghum 60 100 90 100 --Soybean 98 100 90 100 --Speedwell 100 100 -- 100 --Sugar beet 100 100 100 100 --Umbrella sedge 100 100 0 100 85Velvetleaf 100 100 100 100 --Wheat 0 100 60 95 --Wild buckwheat 100 100 100 100 --Wild oat 40 100 80 95 --______________________________________ COMPOUNDRate 125 g/ha 1 3 4 12______________________________________PREEMERGENCEBarley Igri 0 100 30 50Bedstraw 100 100 100 100Blackgrass 30 100 90 90Chickweed 100 100 100 0Corn 50 100 70 90Cotton 70 100 100 10Crabgrass 100 100 100 100Downy Brome 0 100 90 50Giant foxtail 100 100 100 100Lambsquarters 100 100 100 100Morningglory 100 100 100 100Pigweed 100 100 100 100Rape 100 100 100 100Ryegrass 20 100 95 90Sorghum 60 100 90 100Soybean 100 100 100 100Speedwell 100 100 -- 100Sugar beet 100 100 100 100Velvetleaf 100 100 100 100Wheat 0 100 85 100Wild buckwheat 100 100 100 100Wild oat 0 100 75 90______________________________________ COMPOUNDRate 62 g/ha 1 3 4 11______________________________________POSTEMERGENCEBarley Igri 0 95 50 90Barnyard 2 leaf -- -- 100 --Barnyardgrass 100 100 100 100Bedstraw 100 100 100 100Blackgrass 50 100 95 100Chickweed 100 100 100 100Corn 20 98 80 100Cotton 100 100 100 100Crabgrass 20 100 90 100Downy Brome 0 100 75 90Duck salad 0 90 0 90Giant foxtail 80 100 95 100Lambsquarters 100 100 100 100Morningglory 100 100 100 100Pigweed 100 100 100 100Rape 100 100 100 100Rice Japonica 90 100 95 100Ryegrass 40 100 70 90Sorghum 30 100 85 100Soybean 98 100 100 100Speedwell 100 100 100 --Sugar beet 100 100 100 100Umbrella sedge 90 100 0 90Velvetleaf 100 100 100 100Wheat 0 100 60 90Wild buckwheat 100 100 100 100Wild oat 40 100 60 95PREEMERGENCEBarley Igri 0 100 60 90Bedstraw 100 100 100 100Blackgrass -- 100 85 100Chickweed 100 100 100 100Corn 0 100 70 100Cotton 0 98 100 100Crabgrass 80 100 100 100Downy Brome 0 100 75 100Giant foxtail 100 100 100 100Lambsquarters 100 100 100 100Morningglory 100 100 100 100Pigweed 100 100 100 100Rape 50 100 100 100Ryegrass 0 100 95 100Sorghum 50 100 80 100Soybean 30 100 70 100Speedwell 100 100 100 --Sugar beet 100 100 100 100Velvetleaf 100 100 100 100Wheat 0 100 100 100Wild buckwheat 100 100 100 100Wild oat 0 100 70 100______________________________________ COMPOUNDRate 31 g/ha 1 3 4 9 12______________________________________POSTEMERGENCEBarley Igri 0 90 40 80 --Barnyard 2 leaf -- -- -- -- --Barnyardgrass 100 100 95 100 70Bedstraw 100 100 100 100 --Blackgrass 30 100 60 80 --Chickweed 90 100 100 100 --Corn 20 70 60 90 --Cotton 100 100 100 100 --Crabgrass 0 100 70 90 --Downy Brome 0 100 50 80 --Duck salad 0 75 0 95 0Giant foxtail 20 100 75 98 --Lambsquarters 100 100 100 100 --Morningglory 100 100 90 100 --Pigweed 100 100 100 100 --Rape 100 100 100 100 --Rice Japonica 75 100 90 100 90Ryegrass 30 100 60 95 --Sorghum 20 100 70 95 --Soybean 80 100 90 100 --Speedwell 100 100 -- 100 --Sugar beet 100 100 100 100 --Umbrella sedge 0 85 0 100 80Velvetleaf 100 100 100 100 --Wheat 0 100 50 50 --Wild buckwheat 100 100 100 100 --Wild oat 0 100 50 50 --______________________________________ COMPOUNDRate 31 g/ha 1 3 4 12______________________________________PREEMERGENCEBarley Igri 0 90 0 20Bedstraw 100 100 100 90Blackgrass 0 100 70 40Chickweed 100 100 100 0Corn 0 100 40 60Cotton 0 98 20 0Crabgrass 80 100 100 98Downy Brome 0 100 40 20Giant foxtail 80 100 95 100Lambsquarters 100 100 100 100Morningglory 30 100 100 50Pigweed 100 100 100 100Rape 20 100 40 50Ryegrass 0 100 80 50Sorghum 30 100 70 90Soybean 20 100 70 40Speedwell 100 100 -- 100Sugar beet 100 100 100 100Velvetleaf 100 100 100 100Wheat 0 100 40 50Wild buckwheat 100 100 100 80Wild oat 0 100 30 30______________________________________ COMPOUNDRate 16 g/ha 1 3 4 11______________________________________POSTEMERGENCEBarley Igri 0 30 30 70Barnyard 2 leaf -- -- 70 --Barnyardgrass 100 100 -- 100Bedstraw 100 100 100 100Blackgrass 0 100 40 95Chickweed 90 100 -- 100Corn 10 60 40 80Cotton 100 100 100 100Crabgrass 0 70 30 70Downy Brome 0 90 50 70Duck salad 0 70 0 70Giant foxtail 0 100 50 90Lambsquarters 90 100 -- 100Morningglory 100 100 50 100Pigweed 100 100 100 100Rape 100 100 80 100Rice Japonica 65 100 70 95Ryegrass 0 100 40 90Sorghum 0 98 50 90Soybean 70 100 60 90Speedwell 100 100 100 --Sugar beet 100 100 100 100Umbrella sedge 0 55 0 75Velvetleaf 100 100 100 100Wheat 0 60 30 90Wild buckwheat 100 100 100 100Wild oat 0 60 40 85PREEMERGENCEBarley Igri 0 50 0 70Bedstraw 100 100 100 100Blackgrass -- 100 50 90Chickweed 80 100 100 90Corn 0 80 0 90Cotton 0 98 0 100Crabgrass 50 100 50 100Downy Brome 0 90 10 90Giant foxtail 80 100 60 100Lambsquarters 95 100 100 100Morningglory 0 100 10 100Pigweed 100 100 100 100Rape 20 100 30 100Ryegrass 0 100 60 95Sorghum 20 100 10 100Soybean 0 100 0 100Speedwell 100 100 100 --Sugar beet 80 100 90 100Velvetleaf 95 100 100 100Wheat 0 60 0 90Wild buckwheat 100 100 100 100Wild oat 0 95 0 90______________________________________ COMPOUNDRate 8 g/ha 9 12______________________________________POSTEMERGENCEBarley Igri 60 --Barnyard 2 leaf -- --Barnyardgrass 100 20Bedstraw 100 --Blackgrass 50 --Chickweed 100 --Corn 60 --Cotton 100 --Crabgrass 60 --Downy Brome 50 --Duck salad 80 0Giant foxtail 80 --Lambsquarters 100 --Morningglory 100 --Pigweed 100 --Rape 90 --Rice Japonica 95 45Ryegrass 50 --Sorghum 70 --Soybean 100 --Speedwell 100 --Sugar beet 100 --Umbrella sedge 90 0Velvetleaf 100 --Wheat 30 --Wild buckwheat 100 --Wild oat 30 --______________________________________ COMPOUNDRate 8 g/ha 12______________________________________PREEMERGENCEBarley Igri 0Bedstraw 20Blackgrass 20Chickweed 0Corn 20Cotton 0Crabgrass 50Downy Brome 0Giant foxtail 60Lambsquarters 70Morningglory 20Pigweed 100Rape 20Ryegrass 20Sorghum 20Soybean 20Speedwell 70Sugar beet 20Velvetleaf 100Wheat 20Wild buckwheat 30Wild oat 20______________________________________ COMPOUNDRate 4 g/ha 3 4 11______________________________________POSTEMERGENCEBarley Igri -- 20 40Barnyard 2 leaf -- 20 --Barnyardgrass 50 -- 80Bedstraw -- 70 80Blackgrass -- 40 50Chickweed -- -- 60Corn -- 30 50Cotton -- 60 100Crabgrass -- 20 50Downy Brome -- 30 50Duck salad 0 0 0Giant foxtail -- 30 60Lambsquarters -- -- 100Morningglory -- 50 90Pigweed -- 30 60Rape -- 50 80Rice Japonica 25 35 90Ryegrass -- 30 75Sorghum -- 40 50Soybean -- 40 80Speedwell -- 70 --Sugar beet -- 90 85Umbrella sedge 0 0 30Velvetleaf -- 30 100Wheat -- 30 50Wild buckwheat -- 60 90Wild oat -- 20 60______________________________________ COMPOUNDRate 4 g/ha 4 11______________________________________PREEMERGENCEBarley Igri 0 30Bedstraw 20 100Blackgrass 10 30Chickweed 70 70Corn 0 60Cotton 0 80Crabgrass 0 85Downy Brome 0 50Giant foxtail 20 90Lambsquarters 50 100Morningglory 0 30Pigweed 100 100Rape 0 70Ryegrass 0 60Sorghum 0 60Soybean 0 60Speedwell 30 --Sugar beet 0 95Velvetleaf 20 100Wheat 0 40Wild buckwheat 0 100Wild oat 0 50______________________________________ COMPOUNDRate 2 g/ha 9 12______________________________________POSTEMERGENCEBarley Igri 30 --Barnyard 2 leaf -- --Barnyardgrass 85 0Bedstraw 100 --Blackgrass 40 --Chickweed 100 --Corn 40 --Cotton 90 --Crabgrass 40 --Downy Brome 30 --Duck salad 30 0Giant foxtail 50 --Lambsquarters 100 --Morningglory 70 --Pigweed 100 --Rape 60 --Rice Japonica 80 20Ryegrass 30 --Sorghum 50 --Soybean 80 --Speedwell 100 --Sugar beet 85 --Umbrella sedge 90 0Velvetleaf 100 --Wheat 25 --Wild buckwheat 100 --Wild oat 25 --______________________________________ COMPOUNDRate 2 g/ha 12______________________________________PREEMERGENCEBarley Igri 0Bedstraw 0Blackgrass 0Chickweed 0Corn 0Cotton 0Crabgrass 20Downy Brome 0Giant foxtail 20Lambsquarters 0Morningglory 20Pigweed 20Rape 0Ryegrass 0Sorghum 0Soybean 0Speedwell 0Sugar beet 0Velvetleaf 20Wheat 0Wild buckwheat 20Wild oat 0______________________________________ COMPOUNDRate 1 g/ha 3 4 11______________________________________POSTEMERGENCEBarley Igri -- 10 20Barnyard 2 leaf -- 10 --Barnyardgrass 20 -- 0Bedstraw -- 30 70Blackgrass -- 20 30Chickweed -- -- 30Corn -- 20 30Cotton -- 20 90Crabgrass -- 10 10Downy Brome -- 10 20Duck salad 0 0 0Giant foxtail -- 20 20Lambsquarters -- -- 100Morningglory -- 40 85Pigweed -- 30 60Rape -- 10 40Rice Japonica 0 20 45Ryegrass -- 10 30Sorghum -- 20 20Soybean -- 20 50Speedwell -- 10 --Sugar beet -- 40 70Umbrella sedge 0 0 20Velvetleaf -- 20 60Wheat -- 10 20Wild buckwheat -- 20 50Wild oat -- 10 20______________________________________ COMPOUNDRate 1 g/ha 4 11______________________________________PREEMERGENCEBarley Igri 0 0Bedstraw 0 10Blackgrass 0 0Chickweed 0 70Corn 0 0Cotton 0 10Crabgrass 0 10Downy Brome 0 0Giant foxtail 10 20Lambsquarters 0 100Morningglory 0 10Pigweed 60 50Rape 0 0Ryegrass 0 10Sorghum 0 0Soybean 0 0Speedwell 0 --Sugar beet 0 20Velvetleaf -- 100Wheat 0 0Wild buckwheat 0 60Wild oat 0 10______________________________________
TEST C
Compounds evaluated in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Test compounds were applied within approximately one day after planting seeds for the preemergence test.
Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include winter barley (Hordeum vulgare cv. `Igri`), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), downy brome (Bromus tectorum), field violet (Viola arvensis), galium (Galium aparine), green foxtail (Setaria viridis), kochia (Kochia scoparia), lambsquarters (Chenopodium album), speedwell (Veronica persica), rape (Brassica napus), ryegrass (Lolium multiflorum), sugar beet (Beta vulgaris cv. `US1`), sunflower (Helianthus annuus cv. `Russian Giant`), spring wheat (Triticum aestivum cv. `ERA`), winter wheat (Triticum aestivum cv. `Talent`), wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), and wild radish (Raphanus raphanistrum).
Blackgrass, galium and wild oat were treated at two growth stages. The first stage (1) was when the plants had two to three leaves. The second stage (2) was when the plants had approximately four leaves or in the initial stages of tillering. Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table C, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) indicates no test result.
TABLE C______________________________________ COMPOUNDRate 125 g/ha 12______________________________________PREEMERGENCEBlackgrass (1) 30Blackgrass (2) 30Chickweed 0Downy brome 40Field violet 100Galium (1) 100Galium (2) 100Green foxtail 100Kochia 100Lambsquarters 100Persn Speedwell 100Rape 80Ryegrass 90Sugar beet 100Sunflower 25Wheat (Spring) 50Wheat (Winter) 60Wild buckwheat 100Wild mustard 100Wild oat (1) 80Wild oat (2) 90Wild radish 100Winter Barley 50______________________________________ COMPOUNDRate 64 g/ha 1______________________________________POSTEMERGENCEBlackgrass (1) 0Blackgrass (2) 0Chickweed 55Downy brome 0Field violet 100Galium (1) 94Galium (2) 100Green foxtail 35Kochia 90Lambsquarters --Persn Speedwell 70Rape 90Ryegrass 60Sugar beet 100Sunflower 55Wheat (Spring) 0Wheat (Winter) 0Wild buckwheat 100Wild mustard 100Wild oat (1) 0Wild oat (2) 0Wild radish 85Winter Barley 0______________________________________ COMPOUNDRate 64 g/ha 1 12______________________________________PREEMERGENCEBlackgrass (1) 20 10Blackgrass (2) 20 20Chickweed 100 0Downy brome 20 20Field violet 80 100Galium (1) 100 100Galium (2) 100 100Green foxtail 100 100Kochia 100 90Lambsquarters -- 100Persn Speedwell 100 100Rape 65 60Ryegrass 85 60Sugar beet 100 100Sunflower 25 20Wheat (Spring) 0 40Wheat (Winter) 0 45Wild buckwheat 100 100Wild mustard 100 100Wild oat (1) 25 50Wild oat (2) 30 55Wild radish 60 80Winter Barley 0 30______________________________________ COMPOUNDRate 32 g/ha 1 9______________________________________POSTEMERGENCEBlackgrass (1) 0 40Blackgrass (2) 0 50Chickweed 25 100Downy brome 0 40Field violet 100 100Galium (1) 60 100Galium (2) 65 100Green foxtail 0 100Kochia 60 100Lambsquarters -- 100Persn Speedwell 55 100Rape 50 100Ryegrass 30 100Sugar beet 100 100Sunflower 30 60Wheat (Spring) 0 55Wheat (Winter) 0 40Wild buckwheat 95 100Wild mustard 90 100Wild oat (1) 0 60Wild oat (2) 0 80Wild radish 50 --Winter Barley 0 40______________________________________ COMPOUNDRate 32 g/ha 1 12______________________________________PREEMERGENCEBlackgrass (1) 0 0Blackgrass (2) 0 0Chickweed 85 0Downy brome 0 20Field violet 60 80Galium (1) 75 80Galium (2) 70 100Green foxtail 100 --Kochia 90 90Lambsquarters -- 100Persn Speedwell 90 100Rape 35 0Ryegrass 70 10Sugar beet 95 100Sunflower 0 0Wheat (Spring) 0 20Wheat (Winter) 0 25Wild buckwheat 85 100Wild mustard 70 100Wild oat (1) 0 20Wild oat (2) 0 40Wild radish 45 50Winter Barley 0 25______________________________________ COMPOUNDRate 16 g/ha 1 9______________________________________POSTEMERGENCEBlackgrass (1) 0 35Blackgrass (2) 0 20Chickweed 0 100Downy brome 0 40Field violet 75 100Galium (1) 30 100Galium (2) 30 100Green foxtail 0 100Kochia 20 100Lambsquarters -- 100Persn Speedwell 30 100Rape 25 80Ryegrass 0 70Sugar beet 90 100Sunflower 0 --Wheat (Spring) 0 50Wheat (Winter) 0 30Wild buckwheat 65 100Wild mustard 55 100Wild oat (1) 0 60Wild oat (2) 0 60Wild radish 25 100Winter Barley 0 40______________________________________ COMPOUNDRate 16 g/ha 1 12______________________________________PREEMERGENCEBlackgrass (1) 0 0Blackgrass (2) 0 0Chickweed 55 0Downy brome 0 10Field violet 30 40Galium (1) 50 30Galium (2) 45 40Green foxtail 80 70Kochia 60 0Lambsquarters -- 80Persn Speedwell 45 100Rape 0 0Ryegrass 40 0Sugar beet 65 100Sunflower 0 0Wheat (Spring) 0 10Wheat (Winter) 0 10Wild buckwheat 60 70Wild mustard 50 70Wild oat (1) 0 0Wild oat (2) 0 30Wild radish 20 0Winter Barley 0 10______________________________________ COMPOUNDRate 8 g/ha 1 9______________________________________POSTEMERGENCEBlackgrass (1) 0 35Blackgrass (2) 0 0Chickweed 0 100Downy brome 0 40Field violet 35 100Galium (1) 0 100Galium (2) 0 100Green foxtail 0 75Kochia 0 100Lambsquarters -- 100Persn Speedwell 0 100Rape 0 50Ryegrass 0 30Sugar beet 60 100Sunflower 0 60Wheat (Spring) 0 30Wheat (Winter) 0 20Wild buckwheat 25 100Wild mustard 20 60Wild oat (1) 0 20Wild oat (2) 0 40Wild radish 0 50Winter Barley 0 20______________________________________ COMPOUNDRate 8 g/ha 1______________________________________PREEMERGENCEBlackgrass (1) 0Blackgrass (2) 0Chickweed 25Downy brome 0Field violet 0Galium (1) 30Galium (2) 25Green foxtail 35Kochia 35Lambsquarters --Persn Speedwell 20Rape 0Ryegrass 20Sugar beet 45Sunflower 0Wheat (Spring) 0Wheat (Winter) 0Wild buckwheat 30Wild mustard 20Wild oat (1) 0Wild oat (2) 0Wild radish 0Winter Barley 0______________________________________ COMPOUNDRate 4 g/ha 9______________________________________POSTEMERGENCEBlackgrass (1) 30Blackgrass (2) 0Chickweed 100Downy brome 10Field violet 100Galium (1) 100Galium (2) 100Green foxtail 75Kochia 100Lambsquarters 100Persn Speedwell 100Rape 50Ryegrass 0Sugar beet 100Sunflower 50Wheat (Spring) 20Wheat (Winter) 20Wild buckwheat 50Wild mustard 60Wild oat (1) 10Wild oat (2) 20Wild radish 50Winter Barley 15______________________________________ COMPOUNDRate 2 g/ha 9______________________________________POSTEMERGENCEBlackgrass (1) 20Blackgrass (2) 0Chickweed 100Downy brome 10Field violet 50Galium (1) 100Galium (2) 40Green foxtail 40Kochia 70Lambsquarters 70Persn Speedwell 40Rape 0Ryegrass 0Sugar beet 80Sunflower --Wheat (Spring) 20Wheat (Winter) 20Wild buckwheat --Wild mustard 40Wild oat (1) 10Wild oat (2) 10Wild radish 30Winter Barley 15______________________________________
TEST D
Seeds, rhizomes, or plant parts of alfalfa (Medicago sativa), bermudagrass (Cynodon dactylon), broadleaf signalgrass (Brachiaria plantyphylla), common ragweed (Ambrosia elatior), dallisgrass (Paspalum Dilatatum), goosegrass (Eleusine indica), guineagrass (Panicum maximum), itchgrass (Rottboellia exaltata), johnsongrass (Sorghum halepense), ann bluegrass (Poa annua), large crabgrass (Digitaria sanguinalis), P. J. legume (Pueraria javanica), pitted morningglory (Ipomoea lacunosa), peanuts (Arachis hypogaea), purple nutsedge (Cyperus rotundus), sandbur (Cenchrus echinatus), smooth crabgrass (Digitaria ischaemum), common purslane (Portulaca oleracea), TX panicum (Panicum texanum) and yellow nutsedge (Cyperus esculentus) were planted into greenhouse pots containing greenhouse planting medium.
Each pot contained only one plant species. The test compound was dissolved in a non-phytotoxic solvent and applied preemergence and/or postemergence to the plants.
Preemergence applications were made within one day of planting the seeds or plant parts. Postemergence applications were applied when the plants were in the two to four leaf stage (three to twenty cm).
Test chemicals were dissolved in a non-phytotoxic solvent and applied preemergence and postemergence to the plants. Untreated control plants and treated plants were placed in the greenhouse and visually evaluated for injury at 13 to 21 days after herbicide application.
Plant response ratings, summarized in Table D, are based on a 0 to 100 scale where 0 is no injury and 100 is complete control. A dash (-) response indicates no test result.
TABLE D__________________________________________________________________________ COMPOUNDRate 1000 g/ha 8__________________________________________________________________________POSTEMERGENCEAlfalfa Var. 30Ann Bluegrass 30Bermudagrass 60Brdlf Sgnlgrass 70Cmn Purslane 90Cmn Ragweed --Dallisgrass 60Goosegrass 60Guineagrass 20Itchgrass 30Johnsongrass 50Large Crabgrass 50P J Legume --Peanuts 70Pit Morninglory 60Purple Nutsedge --S. Sandbur 60Smooth Crabgras 40Texas Panicum 40Yellow Nutsedge --__________________________________________________________________________ COMPOUNDRate 500 g/ha 3 8 16__________________________________________________________________________POSTEMERGENCEAlfalfa Var. 100 40 0Ann Bluegrass 100 40 0Bermudagrass 100 80 0Brdlf Sgnlgrass 100 100 0Cmn Purslane 100 100 30Cmn Ragweed -- -- 0Dallisgrass 100 90 0Goosegrass 100 90 0Guineagrass 100 50 0Itchgrass 100 50 0Johnsongrass 100 70 0Large Crabgrass 100 30 0P J Legume -- -- --Peanuts 90 60 20Pit Morninglory 100 70 0Purple Nutsedge -- 0 --S. Sandbur 100 20 0Smooth Crabgras 100 50 0Texas Panicum 100 20 --Yellow Nutsedge -- 0 --__________________________________________________________________________ COMPOUNDRate 500 g/ha 8 16__________________________________________________________________________PREEMERGENCEAlfalfa Var. 80 0Ann Bluegrass 100 0Bermudagrass 100 90Brdlf Sgnlgrass 100 0Cmn Purslane 100 0Cmn Ragweed -- 20Dallisgrass 100 90Goosegrass 100 80Guineagrass 100 100Itchgrass 80 0Johnsongrass 100 0Large Crabgrass 100 90Peanuts 70 0Pit Morninglory 90 0Purple Nutsedge 80 --S. Sandbur 100 0Smooth Crabgras 100 100Texas Panicum 90 --Yellow Nutsedge 80 --__________________________________________________________________________ COMPOUNDRate 250 g/ha 1 3 4 5 6 8 9 11 12 13 14 15 16 17 18__________________________________________________________________________POSTEMERGENCEAlfalfa Var. 50 100 60 0 10 40 100 100 0 40 30 10 10 0 0Ann Bluegrass 100 100 50 0 0 20 -- 20 0 -- -- -- 0 0 0Bermudagrass 0 100 60 0 0 40 100 100 0 70 0 0 0 0 0Brdlf Sgnlgrass 0 100 770 0 0 20 100 100 0 10 0 0 0 0 0Cmn Purslane 100 100 100 0 0 100 100 100 90 100 80 70 20 20 20Cmn Ragweed 90 100 -- -- -- -- -- -- -- -- -- -- 0 100 100Dallisgrass 50 100 90 0 0 0 100 100 0 70 0 0 0 0 0Goosegrass 20 100 70 0 0 0 100 100 0 90 0 0 0 0 0Guineagrass 0 100 50 0 0 10 100 100 0 0 0 0 0 0 0Itchgrass 0 100 50 0 0 0 100 100 0 40 0 0 0 0 0Johnsongrass 20 100 100 0 0 80 100 100 0 90 0 0 0 0 0Large Crabgrass 0 100 60 0 0 20 100 100 0 100 0 0 0 0 0P J Legume 20 100 -- -- -- -- -- -- -- -- -- -- -- -- --Peanuts 20 100 50 0 10 20 80 90 20 50 0 20 0 30 60Pit Morninglory 0 100 90 0 0 30 100 100 0 50 0 0 0 0 30Purple Nutsedge 0 90 0 0 0 0 70 90 -- 0 0 10 -- 0 0S. Sandbur 0 100 60 0 0 0 100 100 0 0 0 0 0 0 0Smooth Crabgras 0 100 60 0 0 0 100 100 0 0 0 0 0 0 0Texas Panicum 0 100 90 0 0 0 -- -- -- -- -- -- -- -- --Yellow Nutsedge 0 100 0 0 0 0 100 100 -- 0 0 20 -- 0 0PREEMERGENCEAlfalfa Var. 80 100 100 0 0 50 100 100 100 0 0 0 0 20 60Ann Bluegrass 20 100 100 0 0 70 100 100 60 70 0 0 0 0 100Bermudagrass 20 100 100 0 0 100 100 100 100 100 90 30 40 30 100Brdlf Sgnlgrass 0 100 100 0 0 70 100 100 90 0 0 0 0 0 100Cmn Purslane 100 100 100 0 0 100 100 100 100 60 0 0 0 0 0Cmn Ragweed 100 100 -- -- -- -- -- -- -- -- -- -- 0 0 80Dallisgrass 100 100 100 0 0 100 100 100 100 100 90 100 80 20 100Goosegrass 100 100 100 0 0 100 100 100 100 100 90 100 0 90 100Guineagrass 70 100 100 0 0 100 100 100 100 70 0 0 0 60 100Itchgrass 0 100 100 0 0 60 100 100 80 20 0 0 0 0 70Johnsongrass 30 100 100 0 0 90 100 100 100 0 0 0 0 0 770Large Crabgrass 100 100 100 0 0 100 100 100 100 100 90 80 30 70 100Peanuts 0 100 40 0 0 10 30 100 0 10 0 0 0 20 50Pit Morninglory 50 100 80 0 0 70 100 100 60 0 0 0 0 20 60Purple Nutsedge 0 100 10 0 0 80 50 90 -- 0 0 0 -- 0 0S. Sandbur 0 100 100 0 0 70 100 100 100 90 0 0 0 0 100Smooth Crabgras 100 70 100 0 0 100 100 100 100 100 30 100 80 70 100Texas Panicum 90 100 100 0 0 90 -- -- -- -- -- -- -- -- --Yellow Nutsedge 0 90 20 0 0 70 80 90 -- 20 0 0 -- 0 60__________________________________________________________________________ COMPOUNDRate 125 g/ha 1 2 3 8 9 11 12 13 14 15 16__________________________________________________________________________POSTEMERGENCEAlfalfa Var. 50 70 100 0 100 100 0 0 0 0 10Ann Bluegrass -- -- 100 0 -- 0 0 -- -- -- 0Bermudagrass 0 -- 100 0 80 100 0 0 0 0 0Brdlf Sgnlgrass 0 0 100 0 100 100 0 0 0 0 0Cmn Purslane 100 100 100 60 100 100 0 100 70 60 20Cmn Ragweed 50 90 100 -- -- -- -- -- -- -- 0Dallisgrass 0 100 100 0 100 100 0 0 0 0 0Goosegrass 0 80 100 0 100 100 0 0 0 0 0Guineagrass 0 0 100 0 80 100 0 0 0 0 0Itchgrass 0 0 100 0 60 90 0 0 0 0 0Johnsongrass 20 0 100 0 100 100 0 0 0 0 0Large Crabgrass 0 0 100 0 990 100 0 0 0 0 0P J Legume 20 80 90 -- -- -- -- -- -- -- --Peanuts 10 0 100 20 80 80 0 0 0 0 0Pit Morninglory 0 40 100 30 100 100 0 0 0 0 0Purple Nutsedge 0 0 90 0 60 80 -- 0 0 0 --S. Sandbur 0 0 100 0 100 100 0 0 0 0 0Smooth Crabgras 0 -- 100 0 80 80 0 0 0 0 0Texas Panicum 0 0 100 0 -- -- -- -- -- -- --Yellow Nutsedge 0 0 100 0 100 100 -- 0 0 0 --PREEMERGENCEAlfalfa Var. 0 50 100 0 100 100 80 0 0 0 0Ann Bluegrass 0 0 100 10 100 100 0 60 0 0 0Bermudagrass 0 30 100 100 100 100 100 100 70 30 0Brdlf Sgnlgrass 0 0 100 10 100 100 0 0 0 0 0Cmn Purslane 50 100 100 90 100 100 30 20 0 0 0Cmn Ragweed 100 100 100 -- -- -- -- -- -- -- 0Dallisgrass 10 30 100 100 100 100 70 100 20 20 0Goosegrass 10 90 100 100 100 100 100 100 90 90 0Guineagrass 0 0 100 100 100 100 30 100 0 0 0Itchgrass 0 0 100 50 100 100 0 0 0 0 0Johnsongrass 0 0 100 50 100 100 0 30 0 0 0Large Crabgrass 90 0 100 100 100 100 100 100 90 80 0Peanuts 0 0 80 0 80 70 0 0 0 0 0Pit Morninglory 0 0 100 0 100 100 50 0 0 0 0Purple Nutsedge 0 70 90 10 10 80 -- 0 0 0 --S. Sandbur 0 90 100 0 100 100 0 0 0 0 0Smooth Crabgras 20 0 100 100 100 100 90 100 0 0 0Texas Panicum 20 0 100 0 -- -- -- -- -- -- --Yellow Nutsedge 0 0 80 0 30 90 -- 0 0 0 --__________________________________________________________________________ COMPOUNDRate 64 g/ha 3 11 12__________________________________________________________________________POSTEMERGENCEAlfalfa Var. 90 60 0Ann Bluegrass 60 0 0Bermudagrass 70 0 0Brdlf Sgnlgrass 100 30 0Cmn Purslane 100 100 40Cmn Ragweed -- -- --Dallisgrass 100 0 0Goosegrass 100 30 0Guineagrass 100 0 0Itchgrass 70 0 0Johnsongrass 100 40 0Large Crabgrass 100 0 0P J Legume -- -- --Peanuts 100 30 0Pit Morninglory 100 30 0Purple Nutsedge 80 -- --S. Sandbur 90 0 0Smooth Crabgras 80 0 0Texas Panicum 100 -- --Yellow Nutsedge 100 -- --PREEMERGENCEAlfalfa Var. 100 100 20Ann Bluegrass 100 60 0Bermudagrass 100 100 90Brdlf Sgnlgrass 100 100 0Cmn Purslane 100 100 80Cmn Ragweed -- -- --Dallisgrass 100 100 100Goosegrass 100 100 100Guineagrass 100 100 90Itchgrass 100 100 0Johnsongrass 100 100 50Large Crabgrass 100 100 100Peanuts 40 60 0Pit Morninglory 100 100 0Purple Nutsedge 80 -- --S. Sandbur 100 100 0Smooth Crabgras 100 100 70Texas Panicum 100 -- --Yellow Nutsedge 80 -- --__________________________________________________________________________ COMPOUNDRate 32 g/ha 3 11__________________________________________________________________________POSTEMERGENCEAlfalfa Var. 80 30Ann Bluegrass 50 0Bermudagrass 70 0Brdlf Sgnlgrass 90 0Cmn Purslane 100 100Cmn Ragweed -- --Dallisgrass 90 0Goosegrass 80 0Guineagrass 40 0Itchgrass 50 0Johnsongrass 100 20Large Crabgrass 20 0P J Legume -- --Peanuts 70 50Pit Morninglory 100 50Purple Nutsedge 20 --S. Sandbur 20 0Smooth Crabgras 40 0Texas Panicum 80 --Yellow Nutsedge 20 --PREEMERGENCEAlfalfa Var. 70 100Ann Bluegrass 90 30Bermudagrass 100 100Brdlf Sgnlgrass 90 30Cmn Purslane 100 100Cmn Ragweed -- --Dallisgrass 100 100Goosegrass 100 100Guineagrass 100 90Itchgrass 100 60Johnsongrass 90 70Large Crabgrass 100 100Peanuts 50 0Pit Morninglory 100 20Purple Nutsedge 60 --S. Sandbur 100 80Smooth Crabgras 100 100Texas Panicum 90 --Yellow Nutsedge 70 --__________________________________________________________________________
TEST E
Plastic windowsill flats were filled with planting medium and sprayed with the test compounds formulated in a non-phytotoxic spray solution. Treated soil was then placed in plastic bags and shaken thoroughly to incorporate the compounds in the soil. Seedings of cabbage (Early Copenhagen variety) and tomato (Rutgers Select and Ramapo VF FL hybrid varieties) were transplanted into the spiked soil. Untreated or antidote (naphthalic anyhdride) treated corn seeds were also planted into the spiked soil.
Plants were visually rated and compared with the appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table E.
TABLE E__________________________________________________________________________ Rate Tomato Tomato Corn CornCOMPOUND g/ha Cabbage Rutgers Ramapo Untreated Treated__________________________________________________________________________ (14 DAT) (10 DAT)3 4 10 15 15 0 0 8 45 85 75 0 0 16 70 100 100 40 0 32 100 100 100 70 10 64 100 100 100 80 30 (32 DAT) (28 DAT)3 4 0 0 0 0 0 8 10 100 45 0 0 16 60 100 100 25 0 32 100 100 100 65 40 64 100 100 100 90 70 (14 DAT) (10 DAT)8 32 0 0 0 0 0 64 0 0 0 0 0 125 10 0 0 0 0 250 65 15 5 0 0 500 60 55 55 0 0 (32 DAT) (28 DAT)8 32 0 0 0 0 0 64 0 0 0 0 0 125 0 0 0 0 0 250 50 0 0 10 0 500 55 30 20 10 0__________________________________________________________________________
TEST F
Sugarcane varieties CP70-321 and CP70-330 were planted in 15.2 cm plastic pots which were also seeded with large crabgrass (Digitaria sanguinalis) and Lalang (Imperata cylindrica) rhizomes were planted in 20.3 cm plastic pots which also had volunteer fern (Nephrolepis pectinata) plants growing in them. In another test, guineagrass (Panicum maximum), Paspalum conjugatum, Asystasia intrusa and Nephrolepis pectinata plants were grown in planting medium in plastic pots. The plants were treated postemergence with the test compounds formulated in a non-phytotoxic spray solution.
Treated plants were visually rated at the end of the test and compared with the appropriate controls. Injury ratings werebased on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shownin Table F.
TABLE F__________________________________________________________________________ Rate Sugarcane LargeCOMPOUND g/ha CP70-321 CP70-330 Crabgrass Lalang Fern__________________________________________________________________________ 3 32 0 0 50 30 0 64 0 0 60 30 0 125 0 0 85 30 0 8 500 0 0 0 0 0 1000 0 0 30 30 0 2000 0 0 60 60 20__________________________________________________________________________ Rate Paspalum Asystasia NephrolepisCOMPOUND g/ha Guineagrass Conjugalum intrusa pectinate__________________________________________________________________________11 64 40 0 45 0 125 50 0 40 0 250 75 30 50 0 500 80 45 60 012 64 0 0 0 0 125 0 0 0 0 250 30 0 0 0 500 30 0 0 0__________________________________________________________________________
TEST G
Sugarcane (Saccharum officinarum), purple nutsedge (Cyperus rotundus), Brachiaria decumbens and Brachiaria plantaginea were planted in fiberglass trays. Plants were treated postemergence with the test compounds formulated in a non-phytotoxic spray solution.
Treated plants were visually rated and compared with appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table G.
TABLE G______________________________________COM- Rate Purple Brachiaria BrachiariaPOUND g/ha Sugarcane nutsedge decumbens plantaginea______________________________________ 8 500 0 20 90 60 1000 0 30 100 100 2000 20 60 100 10011 32 0 0 0 0 64 10 0 70 60 125 30 0 90 9012 64 0 0 0 0 125 0 0 0 0______________________________________
TEST H
Pineapple (Ananas comosus), guineagrass (Panicum maximum) and swollen fingergrass (Chloris inflata) were planted in potting medium. Plants were treated postemergence with the test compound formulated in a non-phytotoxic spray solution.
Treatments were visually rated and compared with the appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table H.
TABLE H______________________________________ Rate SwollenCOMPOUND g/ha Pineapple Guineagrass fingergrass______________________________________8 250 0 0 0 500 0 0 0 1000 0 30 0 2000 0 40 80______________________________________
TEST I
Cuttings of turf species Zoysia spp., and St. Augustine (Stenotaphrum secundatum) were planted in 11.4 cm plastic pots filled with planting medium. Smooth crabgrass (Digitaria ischaemum) and large crabgrass (Digitaria sanguinalis) seeds were also planted and grown in 11.4 cm plastic pots. Plants were treated postemergence with the test compounds.
Treatments were visually rated at the end of the test and compared with the appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table I.
TABLE I______________________________________COM- Rate St. Smooth LargePOUND g/ha Zoysia Augustine Crabgrass Crabgrass______________________________________3 4 0 0 0 0 8 0 0 0 0 16 0 0 10 40 32 0 0 10 50 64 0 0 30 708 64 0 0 0 0 125 30 0 0 50 250 50 20 20 90 500 50 20 40 90______________________________________
TEST J
Fifteen different soybean varieties including Williams, W-20 and the Asgrow varieties A3242, A3935, A4715, A5979, A3322, A4009, A4906, A6297, A3205, A3733, A4595, A5403 and A6961 were planted separately in plastic pots filled with planting medium. The pots were tested preemergence with the test chemicals formulated in a non-phytotoxic spray solution.
Plants were visually rated at the end of the test and compared with the appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table J.
TABLE J__________________________________________________________________________ RateCOMPOUND g/ha Williams W20 A3205 A3242 A3322 A3733 A3935 A4009__________________________________________________________________________11 16 20 20 20 20 20 30 20 40 32 60 50 50 60 50 50 70 70 64 90 90 80 90 90 90 90 90 125 100 100 100 100 100 100 100 100__________________________________________________________________________ RateCOMPOUND g/ha A4595 A4715 A4906 A5403 A5979 A6297 A6961__________________________________________________________________________11 16 20 30 60 50 40 60 20 32 60 70 60 60 70 100 100 64 90 90 90 90 90 90 90 125 100 100 100 100 100 100 10012 16 0 0 0 0 0 0 0 32 0 0 0 0 0 0 0 64 0 0 0 0 0 0 0 125 20 20 20 20 20 20 20__________________________________________________________________________
TEST K
Corn, soybean, tomato, morningglory, different nightshade varieties [Solanum nigrum (entire and serrated leaf), S. nigrum subsp. nigrum, S. interius, S. ptycanthus (green berries and black berries), S. nigrum subsp. schultesii and triazine-tolerant nightshade] seeds and potato eye cuttings were planted in separate 11.4 cm plastic pots filled with planting medium. The pots were sprayed preemergence with the test chemicals formulated in a non-phytotoxic spray solvent.
Plants were visually rated at the end of the test and compared with appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table K.
TABLE K__________________________________________________________________________ Triazine Rate TolerantCOMPOUND g/ha Corn Soybean Tomato Morningglory Nightshade Potato__________________________________________________________________________11 2 0 0 0 0 0 0 4 30 20 20 40 0 2012 16 0 0 0 0 0 0 32 0 0 0 20 -- 0 64 0 0 20 40 70 20 125 0 0 60 50 100 60__________________________________________________________________________ S. Nigrum S. Nigrum S. Nigrum S. Ptyanthus Rate Entire Serrated Subs. GreenCOMPOUND g/ha Leaf Leaf Nigrum S. Interius Berries__________________________________________________________________________11 2 0 0 0 0 0 4 0 0 0 0 012 16 0 0 0 0 0 32 0 30 20 70 40 64 0 70 60 100 100 125 60 100 80 100 100__________________________________________________________________________ RateCOMPOUND g/ha S. Ptyanthus Black Berries S. Nigrum Sub. Schultesii__________________________________________________________________________11 2 0 0 4 0 012 16 0 0 32 0 0 64 50 20 125 70 60__________________________________________________________________________
TEST L
Rooted cuttings of rough lemon (Citrus sp.) were planted in 30 liter plastic pots. These pots were also seeded with guineagrass (Panicum maximum), sandbur (Cenchrus enchinatus) and pigweed (Amaranthus viridis). The weeds were cutback many times to simulate mowing and the citrus plant also trimmed.
The citrus was sprayed to simulate field type post-directed herbicide application while the weeds were treated postemergence over the top with the test compounds formulated in a non-phytotoxic spray solvent. In a separate test, loblolly pine seedlings were also sprayed over-the-top with the test compounds formulated in a non-phytotoxic spray solvent. Treated plants were visually rated and compared with appropriate controls. The injury ratings are based on the scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. The results are shown in Tables L1 and L2. The differences in results may be due to the fact that the tests were conducted using plants at different stages of growth.
TABLE L1______________________________________ COMPOUNDRate (500 g/ha) 1 2 3______________________________________POST-DIRECTEDRough Lemon 0 0 0______________________________________ COMPOUNDRate (50 g/ha) 1 2 3______________________________________OVER-THE-TOPGuineagrass 0 0 70Pigweed 0 0 70Sandbur 0 0 0______________________________________ COMPOUNDRate (250 g/ha) 1 2 3______________________________________POST-DIRECTEDRough Lemon 0 0 0OVER-THE-TOPGuineagrass 0 0 30Pigweed 0 0 40Sandbur 0 0 0______________________________________ COMPOUNDRate (125 g/ha) 1 2 3______________________________________POST-DIRECTEDRough Lemon 0 0 0OVER-THE-TOPGuineagrass 0 0 30Pigweed 0 0 0Sandbur 0 0 0______________________________________
TABLE L2______________________________________ COMPOUNDRate (250 g/ha) 3 5 6 8______________________________________POST-DIRECTEDRough Lemon 30* 0 0 0OVER-THE-TOPLoblolly pine 70 0 0 0Guineagrass 70 0 0 20Pigweed 20 0 0 40Sandbur 60 0 0 30______________________________________ COMPOUNDRate (125 g/ha) 8______________________________________POST-DIRECTEDRough Lemon 0OVER-THE-TOPLoblolly pine 0Guineagrass 10Pigweed 30Sandbur 10______________________________________ *Compound contacted leaves after treatment.

Number	Name	Date	Kind
4056527	Schlee et al.	Nov 1977
4859229	Wenger et al.	Aug 1989

Number	Date	Country
0255047	Feb 1988	EPX
0260621	Mar 1988	EPX
0438209	Jul 1991	EPX
0408382	Nov 1991	EPX
0476697	Mar 1992	EPX
3712782	Nov 1988	DEX
3-77874	Apr 1991	JPX
WO9107392	May 1991	WOX
WO9107393	May 1991	WOX

Pyrimidine compounds as herbicides

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