HERBICIDAL ACYLATED AMINO-(PHENYL- OR PYRIDINYL- OR THIENYL-)-PHENYL DERIVATIVES

Abstract: The invention comprises certain substituted phenylamine compounds, agriculturally suitable compositions thereof and a method for controlling undesired vegetation by applying compounds or compositions comprising certain substituted phenylamine compounds.

Description: TITLE Herbicidal Acylated amino-(phenyl- or pyridinyl- or th1enyl-)-phenylderivat1ves This invention relates to certain substituted 5 phenylamine compounds which are useful as herbicides and their agriculturally suitable compositions as well as V methods for their use as general or selective preemergent its or postemergent herbicides or as plant growth regulants. New compounds effective for controlling the growth of 10 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 cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause 15 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 20 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 25 The invention comprises a method for controlling the growth of undesired vegetation by the preemergent and/or postemergent application to the locus to be protected of an effective amount of compounds of Formula I: 30 wherein Q is Q-3 Q-4 R is H, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy, c i _c 2 haloalkoxy, C^C^ haloalkylthio, halogen, CN or N0 2 ; Y is NR 7 C(0)XR 3 ; X is a single bond, O, S or NR 4 ; R 1 is H, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, c l _< ~3 alkylthio, C 2 -C 3 alkynyl, C 2 -C 3 alkoxyalkyl, C 2 -C 3 alkylthioalkyl, halogen, N0 2 , CN, NHR 5 or NR 5 R 6 ; R 3 is C -Cs alkyl optionally substituted with C 1 -C alkoxy, OH, 1-3 halogens, OC (0) (C 1 -C alkyl) or c ι~ c 2 alkylthio; CH 2 (C 3 -C 4 cycloalkyl) ; C 3 -C 4 cycloalkyl optionally substituted with 1-3 CH 3 's, 1-2 F*s or 1-2 Cl's; C 2 -C 4 alkenyl; C 2 -C 4 haloalkenyl; C 3 -C 4 alkynyl; C(0) (C 1 -C 2 alkyl); benzyl; or a 5- or 6-membered heterocyclic ring containing one heteroatom selected from 0, N and S, each ring optionally substituted with halogen or CH 3 ; R 4 is H, Cτ-C-2 alkyl or 0CH 3 ; R 5 and R 6 are independently C 1 -C 2 alkyl; R 7 is H, C 1 -C 2 alkyl or C(0)R 8 ; R 8 is Ci-Cs alkyl optionally substituted with C 1 -C 2 alkoxy, OH, 1-3 halogens, OC(0) (C 1 -C 2 alkyl) or C x -C 2 alkylthio; CH 2 (C 3 -C 4 cycloalkyl); C 3 -C 4 cycloalkyl optionally substituted with 1-3 CH 3 's, 1-2 F's or 1-2 Cl's; C 2 -C 4 alkenyl; C 2 -C 4 haloalkenyl; C 3 -C 4 alkynyl; C(0) (C 1 -C 2 alkyl); benzyl; or a 5- or β-membered heterocyclic ring containing one heteroatom selected from O, N and S, each ring optionally substituted with halogen or CH 3 ; and n is 0 or 1; provided that when R 3 is C 2 alkenyl, C haloalkenyl or a heterocyclic ring then X is a single bond. In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl", includes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers. Alkoxy includes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy isomers. Alkenyl includes straight chain or branched alkenes, e.g., 1-propenyl, 2-propenyl, 3-propenyl and the different buten'yl isomers. Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. 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 2 CH 2 F, CF 2 CF 3 and CH 2 CHFC1. Representative exemplification of heterocyclic rings includes but is not limited to pyrrole, furan, thiophene and pyridine. The preferred methods of use of the invention for reasons including ease of synthesis and/or greater herbicidal efficacy involve: 1. Compounds of Formula I wherein R is C x -C 2 haloalkyl, C 1 -C 2 haloalkoxy, Cτ . -C 2 haloalkylthio, halogen or CN; 2. Compounds of Preferred 1 wherein R 1 is C 1 -C 2 alkyl, Cι~C 2 alkoxy, C 1 -C 2 alkylthio, C 2 -C 3 alkoxyalkyl, C 2 -C 3 alkylthioalkyl, Cl, Br, CN, NHR 5 or NR 5 R 6 ; and R 7 is H; 3. Compounds of Preferred 2 wherein Q is Q-l or Q-2; and R 3 is C 1 -C 4 alkyl optionally substituted with C 1 -C 2 alkoxy; CH 2 (C 3 -C 4 cycloalkyl); C 3 -C 4 cycloalkyl optionally substituted with 1-3 CH 3 's; or C 2 -C 4 alkenyl; 4. Compounds of Preferred 3 wherein R is ^-C^ fluoroalkyl, C 1 -C fluoroalkoxy, C -C 2 fluoroalkylthio, Cl, Br or CN; Specifically preferred methods for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy are the method of Preferred 4 involving 1-methylethyl [5-methyl-3'-(trifluoromethyl) [1,1'- biphenyl]-2-yl]carbamate and 3-methyl-N-[5-methyl-3'- (trifluoromethyl) [1,1'-biphenyl]-2-yl]butanamide. The invention also comprises novel compounds of Formula I and agriculturally suitable compositions containing them. wherein Q is R is H, C 2 -C 2 alkyl, ^__-C 2 haloalkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, C ] .-C2 haloalkylthio, halogen, CN or N0 2 ; Y is NR 7 C(C R 3 ; X is a single bond, 0, S or NR 4 ; R 1 is H, C 1 -C 3 alkyl, C-^^ alkoxy, ^^3 haloalkoxy, C ! -C 3 alkylthio, C 2 -C 3 alkoxyalkyl, C 2 -C 3 alkylthioalkyl, halogen, N0 2 , CN, NHR 5 or NR 5 R 6 ; R 3 is C 2 -C 5 alkyl optionally substituted with C 1 -C 2 alkoxy, OH, 1-3 halogens, OC (O) (C 1 -C 2 alkyl) or C 1 -C 2 alkylthio; CH 2 (C 3 -C cycloalkyl); C 3 -C 4 cycloalkyl optionally substituted with 1-3 CH 3 's, 1-2 F's or 1-2 Cl's; C 2 -C 4 alkenyl; C 2 -C 4 haloalkenyl; C 3 -C 4 alkynyl; C(0) (C 1 -C 2 alkyl); benzyl; or a 5- or 6-membered heterocyclic ring containing one heteroatom selected from 0, N and S, each ring optionally substituted with halogen or CH 3 ; R 4 is H, C 1 -C 2 alkyl or 0CH 3 ; R 5 and R 6 are independently 1 -C 2 alkyl; and R 7 is H, C 1 -C 2 alkyl or C(0)R 8 ; R 8 is C x -C5 alkyl optionally substituted with Ci-C 2 alkoxy, OH, 1-3 halogens, OC (0) (C 1 -C 2 alkyl) or C -C 2 alkylthio; CH 2 (C 3 -C 4 cycloalkyl); ^-C^ cycloalkyl optionally substituted with 1-3 CH 3 's, 1-2 F's or 1-2 Cl's; C 2 -C 4 alkenyl; C 2 -C 4 haloalkenyl; C 3 -C 4 alkynyl; C(0) (C 1 -C 2 alkyl); benzyl; or a 5- or 6-membered heterocyclic ring containing one heteroatom selected from 0, N and S, each ring optionally substituted with halogen or CH 3 ; n is 0 or 1; provided that (a) when R 3 is C 2 alkenyl, C 2 haloalkenyl or a heterocyclic ring then X is a single bond and (b) when Q is Q-l, R 1 is H and Y is NHC(0)CH 3 then R is other than Br or F. The preferred compounds and compositions of the invention are the compounds and compositions involving the compounds set forth above in the preferred methods of use. PETAILEP DESCRIPTION OF THE INVENTION Compounds of General Formula I can be readily prepared by one skilled in the art by using the reactions and techniques described in Schemes 1-10 of this section as well as by following the specific procedures given in Examples 1-22. Scheme 1 illustrates the preparation of compounds of General Formula I (where R, R 1 and Y are defined as above) whereby aromatic compounds of General Formula IV where X 1 is bromine, iodine or trifluoromethylsulfonyloxy (OTf) can be coupled with substituted aryl compounds of Formula III 1 _ 5 where X 2 is a trialkyltin (e.g., Me3S ) , trialkylsilyl (e.g., Me 3 Si) , or boronic acid (e.g., B(OH) 2 ) moiety. The coupling is carried out by methods known in the art: for example, see Tsuji, J., Organi c Synthesis with Palladium Compounds, Springer-Verlag, Berlin 1980; Negishi, E., Ace. Chem . Res . 1982, 15, 340; Stille, J. K., Angew. Chem . 1986, 98, 504; Yamamoto, A. and Yamagi, A., Chem . Phar . Bull . 1982, 30, 1731 and 2003; Dondoni et al. , Synthesis 1987, 185; Dondoni et al., Synthesis 1987, 693; Hoshino et al . , Bull . Chem . Soc. Jpn . 1988, 61, 3008; Sato, M. et al . , Chem . Lett . 1989, 1405; Miyaura et al . , Syntheti c Commun . 1981, 11, 513; Siddiqui and Sniekus, Tetrahedron Lett . 1988, 29, 5463; Sharp at al . , T rahedron Lett . 1987, 28, 5093; Hatanaka et al . , Chem. Lett. 1989, 1711; Bailey, T. R., Tetrahedron Lett . 1986, 27, 4407 and Echavarren, A. M. and Stille, J. K., J. Am . Chem . Soc . 1987, 109, 5478. The coupling of IV and III 1 _ 5 is carried out by heating in the presence of a transition metal catalyst such as tetrakis (triphenylphosphine) palladium(O) or bis (triphenylphosphine) palladium (II) dichloride in a solvent such as toluene, acetonitrile, glyme, or tetrahydrofuran. As shown in Scheme 1, compounds of General Formula I can also be prepared by coupling aromatic compounds of General Formula IV where X 1 is a trialkyltin (e.g., Me 3 Sn) , trialkylsilyl (e.g., Me 3 Si) or boronic acid (e.g., B(OH) 2 ) moiety with substituted aryl compounds of Formula III 1 _ 5 where X 2 is bromine, iodine, or OTf using the same conditions as described above. Scheme 1 Ill, III: Substituted aryl compounds of General Formula IV and III -. 5 where X 1 and X 2 are bromine, iodine or OTf are either known or readily prepared by procedures and techniques well known in the art, for example: Houbeit- eil, Methoden der Organische Chemie, IV Edition, Eugen Muller, ed., Georg Thieme Verlag. By methods also reported in the above cited literature, treatment of compounds of General Formula IV and III^ where X 1 is bromine or iodine with a base such as n-butyllithium followed by quench with a trialk ltin halide, trialkylsilyl halide, boron trichloride, or trialkyl borate gives compounds of General Formula IV and III^s where X 1 and X 2 respectively are a trialkyltin (e.g., Me 3 Sn) , trialkylsilyl (e.g., Me 3 Si) , or boronic acid (e.g., B(OH) ) moiety-. Compounds of General Formula III^s where X 2 is a trialkyltin (e.g., Me 3 Sn) , trialkylsilyl (e.g., Me 3 Si) , or boronic acid (e.g., B(OH) 2 ) moiety can also be prepared from compounds of General Formula where X 2 is hydrogen by treatment with a base such as n-butyllithium followed by quench with a trialkyltin halide, trialkylsilyl halide, or trialkyl borate as reported in the same literature references, providing that Y is an ortho-directing group known in the art (e.g., tri ethylacetylamido) : for example, Fuhrer, W., J. Org. Chem . , 1979, 44, 1133. The remaining schemes and examples illustrate the preparation of compounds of General Formula I wherein Q is Q-l, but can also be applied to Q-2 through Q-5. Compounds of General Formula I can be readily prepared by one skilled in the art from intermediate compounds of General Formula I where Y is NH 2 or NHR 7 by reaction with appropriate acyl chlorides, acid anhydrides, chloroformates, carbamyl chlorides, or isocyanates under conditions well known in the literature, for example: Sandier, R. S. and Karo, W., Organic Functional Group Preparations, 2nd Edition, Vol . I, 2 ; Vol . II, 152, 260, Academic Press. Schemes 2 and 3 and Examples 5-7 and 13 of this section illustrate examples of the preparation and reactions of intermediates of Formula II . Such intermediates are readily prepared by coupling of aromatic compounds of Formula IV where X 1 is bromine or iodine with substituted aryl compounds of Formula III-^ where Y is NHR 7 and X 2 is a trialkyltin (e.g., Me 3 Sn) , trialkylsilyl (e.g., Me 3 Si) , or boronic acid (e.g., B(OH) 2 ) moiety, or of aromatic compounds of Formula IV where X 1 is a trialkyltin (e.g., Me 3 Sn) , trialkylsilyl (e.g., Me 3 Si) , or boronic acid (e.g., B(OH) 2 ) moiety with substituted aryl compounds of Formula Illi-.s where Y is NHR 4 and X 2 is bromine or iodine under the same conditions as described above. Scheme 2 Intermediate compounds of General Formula II can also be prepared, as illustrated in Scheme 2 and Examples 16 and 17 of this section, by palladium catalyzed coupling of aromatic compounds of General Formula IV where X 1 is a trialkyltin (e.g., Me 3 Sn) , trialkylsilyl (e.g., Me 3 Si) , or boronic acid (e.g., B(OH) 2 ) moiety with substituted aryl compounds of Formula III^s where X 2 is bromine, iodine or OTf and Y is nitro, using the same conditions as described above, and then catalytically or chemically reducing the nitro group in the intermediate compounds of General Formula XII. Such reduction of nitro to amino groups is well documented in the chemical literature. See for example, Ohme, R. and Zubek, A. R. and Zubek, A. in Preparative Organic Chemistry, 557, Hilgetag, G. and Martini, A., Eds., John Wiley £ Sons, New York, 1972. Scheme 3 II, Z=NH 2 or NHR 7 I, 0=0. Alternatively, intermediate compounds of General Formula II where Z is NHR 7 can be prepared from compounds of General Formula V, which contain an appropriately protected primary or secondary amino group, by hydrolysis, hydrogenolysis, or other adequate deprotection procedures, as shown in Scheme 4. Appropriate conditions for such reactions are extensively described in the literature, for example: Theodora W. Green, Protective Groups in Organic Synthesis, Chap. 7, John Wiley & Sons, New York, 1981. Scheme 4 V, R 8 =H or C _ 2 alkyl II, Z=NH 2 or NHR' A=protective group Compounds of General Formula VII containing a urethane or urea moiety can be prepared by one skilled in the art from intermediate compounds of General Formula VI containing an isocyanate moiety by reaction with appropriate alcohols or amines, respectively, as shown in Scheme 5 and well documented in the literature: for example, Sandier, R. S. and Karo, W., Organic Functional Group Preparations, 2nd Edition, Vol. II, 152, 260, Academic Press. Scheme 5 VI VII, X=0 or NR S Such isocyano intermediates of Formula VI can be prepared from intermediate compounds of General Formula VIII by reaction with phosgene or a safer phosgene replacement (e.g., diphosgene or triphosgene) as illustrated in Scheme 6 and Example 4 of this section, using procedures and techniques known in the literature: for example, Lehman, G. and Teichman, H. in Preparative Organic Chemistry, 472, Hilgetag, G. and Martini, A., Eds., John Wiley & Sons, New York, 1972; Eckert, H. and Forster, B., Angew. Chem. Int . Ed. , 1987, 26, 894; Babad, H. and Zeiler, A. G., C eiπ.-Rev., 1973, 73, 75. Scheme 6 VIII VI Compounds of General Formula X can be prepared from compounds of General Formula XI by reaction with the appropriate C 1 to C 2 alkyl halide, sulfate, or other adequate equivalent as described and illustrated in Scheme 7 and Example 15, using published procedures and techniques: for example, Lehman, G. and Teichman, H. in Preparative Organic Chemistry, 455-6, Hilgetag, G. and Martini, A., Eds., John Wiley & Sons, New York, 1972; Pachter, I. J. and Kloetzel, M. C, J. A er. Chem . Soc , 1952, 74, 1321. Scheme XI X Compounds of General Formula XIII can be prepared from compounds of General Formula XII, where Z is a primary or secondary amine, amide, urethane, or urea by reaction with a halogen, nitric acid or nitric oxide under the appropriate conditions, as illustrated in Scheme 8 and Example 20 and thoroughly described in the chemical literature; for example see, Dorn, H. in Preparative Organic Chemistry, Hilgetag, G. and Martini, A., Eds., John Wiley & Sons: New York, 1972, p. 150. Scheme 8 XII, R 1 =H XIII, R^Halogen, N0 2 Compounds of General Formula XIII where R 1 is bromine or iodine, can be further elaborated into Compounds of General Formula XIV, as illustrated in Scheme 9 and Examples 20 and 21, under reaction conditions.described in the chemical literature; for example see, Gross, H., Bischoff, Ch., Hδft, E., and Grϋndemann, E. in Preparative Organic Chemistry, Hilgetag, G. and Martini, A., Eds., John Wiley & Sons: New York, 1972, p. 923; Takahashi, S., Kuroyama, Y., Sonogashira, K., and Hagihara, N., Synthesis, 1980, 627; De la Rosa, Martha A., Velarde, Esperanza, and Guzman, A.: Synthetic Communications, 1990, 20, 2059. Scheme 9 XIII, R x =Br, I XIV, R X =CN, alkynyl Compounds of General Formula XIII where R 1 is nitro can be also used to prepare Compounds of General Formula XV and Compounds of General Formula XVI, as illustrated in Scheme 10 using procedures and techniques known in the literature, for example, Lehmann, G. and Teichmann, H. in Preparative Organic Chemistry, Hilgetag, G. and Martini, A., Eds., John Wiley & Sons: New York, 1972, p. 419. Scheme 10 EXAMPLE 1 Preparation of 3-(trifluoromethyl.phenylboronic acid A solution of 50 g (0.222 mol) Λieta-bromobenzotri- fluoride in 175 ml dry ether was cooled at -10°C under nitrogen and 155 ml (0.24 mol) 1.6N n-butyllithium solution in hexanes was added dropwise during 1.5 hrs while maintaining the temperature below 0°C. After complete addition, the lithium salt solution was slowly transferred through a cannula during 30 min, under slight nitrogen pressure, into a solution of 170 g (0.888 mol) triisopropylborate in 150 ml anhydrous tetrahydrofuran at -70 to -60°C. Stirring was continued overnight while allowing the cold bath to melt. The reaction mixture was poured over 200 ml ice-cold 10% hydrochloric acid and stirred for 20 min. Phases were separated, organic phase washed twice with brine, dried and evaporated. The crude product was purified by triturating with hot hexane, to yield 35 g of pure product as white crystals, m.p. 155-6°C. EXAMPLE 2 Preparation of 2.2-dimethyl-N-T5-methyl-3'- f ri luoromethyl) n.1'-biphenyl1-2-yl1-propanamide 22.8 g (0.1 mol) 2-bromo-4-methyl-N-acetylaniline was dissolved under nitrogen in 30 ml glyme, 0.3 g palladium bis (triphenylphosphine) dichloride was added, and the mixture was stirred at the room temperature for 10 min., after which 20.9 g (0.11 mol) jπeta-trifluoromethyl- phenylboronic acid was added, followed by a solution of 25.2 g (0.3 mol) sodium bicarbonate in 300 ml water. The mixture was refluxed under nitrogen with good stirring for 2 hrs. After cooling to about 60°C, the reaction mixture was poured over 300 ml IN sodium hydroxide solution and stirred at the room temperature for 20 min, then extracted with 250 ml ethyl acetate. Organic extracts were washed with brine, dried, and evaporated to dryness. The crude product was purified by chromatography on silica using 20:1 chlorobutane/ethyl acetate mixture as eluent to yield 26.5 g pure product as a white powder, m.p. 110-3°C. X H NMR (CDC1 3 ) : δ 1.98 (s, 3: COCH 3 ) , 2.40 (s, 3: CH 3 ) , 7.02-7.8 (7 aromatic protons, NH) . EXAMPLE 3 Preparation of 5-methyl- '- (trifluoromethyl . fl .1 ' - biphenyl]-2-yll-amine 8 g 2,2-Dimethyl-N- [5-methyl-3 '- (trifluoro- methyl) [1, 1 '-biphenyl] -2-yl] -propanamide was dissolved in 30 ml glacial acetic acid and the mixture warmed up to about 70°C and then 20 ml 15% hydrochloric acid solution was gradually added. After complete addition the reaction mixture was kept at reflux for 4 hrs . After cooling, volatiles were removed in vacuo, the residue was taken in 50 ml water, ice was added, the mixture was neutralized to pH 10 with 5% sodium hydroxide solution and extracted with ether. Organic extracts were washed with brine, dried, and evaporated to dryness. The crude product was purified by chromatography on silica using chlorobutane as eluent to yield 6.2 g pure product as a tan oil. - ■ R NMR (CDC1 3 ) : δ 2.24 (s, 3: Me) 3.58 (s, 2: NH 2 ) 6.6-7.8 (7 aromatic protons) . EXAMPLE 4 Preparation of 5-methyl- '- (tri luoromethyl . π .1 ' - biphenyll-2-yll -isocyanate To a solution of 0.8 g triphosgene in 25 ml dry chloroform 2 g of 5-methyl-3 '- (trifluoromethyl) [1, 1 ' - biphenyl] -2-yl] -amine was added under nitrogen, followed by dropwise addition of 0.7 ml triethylamine. A mildly exothermal reaction occurred. After stirring overnight at the room temperature, aliquots of this reaction mixture were used for further reactions. EXAMPLE 5 Preparation of 3-methyl-N- r5-methyl-3 '- (tri luoromethyl) n.1 '-biphenyl1-2-yl1butana ide To a solution of 2.51 g (0.01 mol) 5-methyl-3'- (trifluoromethyl) [1, 1 '-biphenyl] -2-yl] -amine in 20 ml dry chloroform 1.2 g (0.012 mol) triethylamine was added under nitrogen, followed by dropwise addition of 1.33 g (0.011 mol) 3-methylbutyryl chloride dissoluted in 5 ml dry chloroform. After stirring for 5 hrs at the room temperature, 5 ml water was added and stirring was continued for 20 min. The reaction mixture was diluted with 50 ml methylene chloride, washed with water, then saturated sodium bicarbonate solution and brine, dried, and evaporated to dryness. The crude product was purified by chromatography on silica using 20:1 chlorobutane/ethyl acetate mixture as eluent to yield 3.1 g pure product as a light tan powder, m.p. 89-91°C. --E NMR (CDC1 3 ) : δ 0.95 (d, 6: 2xCH 3 ) , 2.00 (m, 3: CH 2 , CH) , 2.40 (s, 3: CH 3 ) , 6.8 (s, 1: NH) , 7.05-7.65 (7 aromatic protons) . EXAMPLE 6 Preparation of 1-methylethyl-N-r5-methyl- '- (trifluoromethyl) ϊl .1'-biphenyl!-2-yll carbamate To a solution of 2.51 g (0.01 mol) S-methyl-3 1 - (tri luoromethyl) [1,1'-biphenyl]-2-yl]-amine in 20 ml dry chloroform 1.2 g (0.012 mol) triethylamine was added under nitrogen, followed by dropwise addition of 1.35 g (0.011 mol) isopropyl chloroformate dissoluted in 5 ml dry chloroform. After stirring for 2 hrs at the room temperature the reaction mixture was refluxed for 5 min, allowed to cool at the room temperature, 5 ml water was added and stirring continued for 20 min. The reaction mixture was diluted with 50 ml methylene chloride, washed with water, then saturated sodium bicarbonate solution and brine, dried, and evaporated to dryness. The crude product was purified by chromatography on silica using 20:1 chlorobutane/ethyl acetate mixture as eluent to yield 3.1 g pure product as white crystals, m.p. 83-85°C. A H NMR (CDC1 3 ) : δ 1.22 (d, 6: 2xCH 3 ) , 2.38 (s, 3: CH 3 ) , 4.96 (m, 1: CH), 6.2 (s, 1: NH) , 7.02-7.90 (7 aromatic protons) . EXAMPLE 7 Preparation of N. -diethyl-N' - r5-methyl- '- (tri luoromethyl) .l.1 '. biphenyl1-2-yl1 urea To a solution of 2.51 g (0.01 mol) 5-methyl-3'- (trifluoromethyl) [1,1 '-biphenyl]-2-yl] -amine in 20 ml dry chloroform 2 g (0.015 mol) diethylcarbamyl chloride was added under nitrogen and the reaction mixture was refluxed for 5 hrs. After cooling to room temperature, 5 ml water was added and stirring continued for 20 min. The reaction mixture was diluted with 50 ml methylene chloride, washed with saturated sodium bicarbonate solution and brine, dried, and evaporated to dryness. The crude product was purified by chromatography on silica using 10:1 chlorobutane/ethyl acetate mixture as eluent to yield 2.1 g pure product as white crystals, m.p. 87-87°C. A H NMR (CDC1 3 ) : δ 1.00 (t, 6: 2xCH 3 ) , 2.35 (s, 3: CH 3 ), 3.15 (q, 4: 2xNCH 2 ) , 6.1 (s, 1: NH) , 7.02-8.00 (7 aromatic protons) . EXAMPLE 8 Preparation of N-(2-methylpropyl)-N'-r5-methyl-3'- (trifluoromethyl) \ l ,1'-biphenyl]-2-yll urea To 5 ml solution of 5-methyl-3'-(trifluoromethyl)- [1,1'-biphenyl]-2-yl]-isocyanate prepared as described under Example 4 was added under nitrogen 0.17 g (1.2 equiv) isobutylamine and the reaction mixture stirred overnight at the room temperature, then diluted with 25 ml methylene chloride, washed with saturated sodium bicarbonate solution and brine, dried, and evaporated to dryness. The crude product was purified by chromatography ~n silica using 5:1 chlorobutane/ethyl acetate mixture as eluent to yield 0.52 g pure product as white crystals, m.p. 165-7°C. X H NMR (CDCI 3 ) : δ 0.91 (d, 6: 2xCH 3 ) , 1.63 (m, 1: CH) , 2.40 (s, 3: CH 3 ) , 2.96 (t, 2: NCH 2 ) , 4 . 6 (t, 1: NH) , 5.8 (s, 1: NH) , 7.05-7.65 (7 aromatic protons) . EXAMPLE 9 Preparation of cyclopentyl-r5-methyl-3'- (trifluoromethyl) d,1'-biphenyl!-2-yll carbamate To 5 ml solution of 5-methyl-3'-(trifluoromethyl)- [1,1'-biphenyl]-2-yl]-isocyanate prepared as described under Example 4 was added under nitrogen 0.21 g (1.5 equiv) cyclopentyl alcohol and the reaction mixture stirred overnight at the room temperature, then diluted with 25 ml methylene chloride, washed with saturated sodium bicarbonate solution and brine, dried, and evaporated to dryness. The crude product was purified by chromatography on silica using 5:1 chlorobutane/ethyl acetate mixture as eluent to yield 0.21 g pure product. EXAMPLE 10 Preparation of -methyl -2- (trimethyltin)trimethylacetylanilide- 19.1 g (0.1 mol) 4-methyl-N-(trimethylacetyl) niline was dissolved under nitrogen in 250 ml anhydrous tetrahydrofuran and the solution was cooled to -10°C, after which 156 ml (0.25 mol) 1.6N solution of n-butyllithium in hexanes was added dropwise during 1.5 hrs, while maintaining the temperature below 0°C. After complete addition stirring was continued for 0.5 hrs on the cold bath, then overnight at the room temperature. The reaction mixture was cooled to -5°C and a solution of 40 g (0.2 mol) trimethyltin chloride in 100 ml anhydrous tetrahydrofuran was added dropwise during 20 min., while maintaining the temperature below 0°C. After complete addition stirring was continued at 0°C for 4 hrs, then the reaction mixture was poured under nitrogen blanket over 300 ml saturated solution of sodium bicarbonate and stirred for 1 hr. 300 ml Ethyl acetate was added, phases separated, the organic phase washed with brine, dried and evaporated to dryness. The residue was chromatographed on silica using chlorobutane as eluent. 21.3 g of trimethyltin derivative and 6.1 g of starting material were obtained. - ■ H NMR (CDC1 3 ) : δ 0.38 ( s , 9: SnMe 3 ) , 1.30 (s, 9: C(CH 3 ) 3 ), 2.32 (s, 3: CH 3 ) , 7.10-7.7 (3 aromatic protons, NH) . EXAMPLE 11 Preparation of 2,2-dimethyl-N-r5-methyl-3'-cyanofl.1 '- biphenyl]-2-yll-propanamide 7.1 g (0.02 mol) 4-methyl-2- (triir -myltin)trimethyl- acetylanilide was dissolved under nitrogen in 30 ml anhydrous tetrahydrofuran, 0.05 g palladium tetrakis- (triphenylphosphine) was added, and the mixture was stirred at the room temperature for 10 min., after which 4 g (0.022 mol) meta-bromobenzonitrile was added. The mixture was refluxed under nitrogen with good stirring for 7 hrs. After cooling, the reaction mixture was poured over 100 ml saturated sodium bicarbonate solution and stirred at the room temperature for 20 min, then extracted with 100 ml ethyl acetate. Organic extracts were washed with brine, dried, and evaporated to dryness. The crude product was purified by chromatography on silica using chlorobutane as eluent to yield 4.55 g pure product as white crystals, m.p. 78-80°C. X H NMR (CDCI 3 ) : d 1.16 (s,9: C(CH 3 ) 3 ), 2.38 (s,3: CH 3 ) , 7.04-7.9 (7S aromatic protons, NH) . EXAMPLE 12 Preparation of 5-methyl-3- ϊ (trifluoromethyl)- phenyll-2-pyridinamine 4.7 g (0.025 mol) 2-amino-3-bromo-5-methylpyridine was dissolved under nitrogen in 50 ml anhydrous tetrahydrofuran, 0.05 g palladium bis (triphenylphosphine) dichloride was added, and the mixture was stirred at the room temperature for 10 min., after which 5.5 g (0.029 mol) ;neta-trifluoromethylphenylboronic acid was added, followed by a solution of 7.2 g (0.075 mol) sodium carbonate in 70 ml water. The mixture was refluxed under nitrogen with good stirring for 2 hrs. After cooling , the reaction mixture was poured over 100 ml IN sodium hydroxide solution and stirred at the room temperature for 20 min, then extracted with 150 ml ethyl acetate. Organic extracts were washed with brine, dried, and evaporated to dryness. The crude product was purified by chromatography on silica using 20:1 chlorobutane/ethyl acetate mixture as eluent to yield 5.35 g pure product as a light tan solid, m.p. 73-5°C. X H NMR (CDC1 3 ) : δ 2.12 (s, 3: CH 3 ) , 4.40 (s, 2: NH 2 ) , 7.10-8.0 (6 aromatic protons). EXAMPLE 13 Preparation of N-r5-methyl-3-r3-(trifluoromethyl) phenyl1-2-pyridinyl1 cyclopropaneamide To a solution of 0.50 g (0.002 mol) 5-methyl-3- [ (trifluoromethyl)phenyl]-2-pyridinamine in 10 ml dry chloroform 026 g (0.0026 mol) triethylamine was added under nitrogen, followed by dropwise addition of 0.23 g (0.0022 mol) cyclopropancarbonyl chloride dissolved in 2 ml dry chloroform. After stirring for 5 hrs at the room temperature, 5 ml water was added and stirring continued for 20 min. The reaction mixture was diluted with 20 ml methylene chloride, washed with water, then saturated sodium bicarbonate solution and brine, dried, and evaporated to dryness. The crude product was purified by chromatography on silica using 3:1 chlorobutane/ethyl acetate mixture as eluent to yield 0.54 g pure product as a white solid, m.p. 129-31°C. X H NMR (CDCI 3 ) : δ 0.65-0.90 (m, 4: 2xCH 2 ) , 1.85 (m, 1: CH) , 2.40 (s, 3: CH 3 ) , 7.44-8.50: (6 aromatic protons) . EXAMPLE 14 Preparation of N-r5-methyl-3-T3- (trifluoromethyl) phenyl!-2-pyridinyl! cyclopropaneamide N-oxide 0.3 g (1 mmol) N-[5-methyl-3-[3- (trifluoromethyl) phenyl]-2-pyridinyl] cyclopropaneamide was dissolved in 5 ml methylene chloride and 0.42 g (cca. 1.2 mmol) 50-60% /neta-chloroperbenzoic acid was added in two portions at 1 hr interval. The mixture was stirred overnight, diluted with 25 ml methylene chloride and washed with IN sodium thiosulfate, then saturated sodium bicarbonate solution until no meta-chlorobenzoic acid was present. The solution was dried over magnesium sulfate and evaporated to dryness. The crude product was purified by chromatography on silica using 1:1 chlorobutane/ethyl acetate mixture as eluent to yield 0.22 g pure product as white crystals, m.p. 125-7°C. H NMR (CDC1 3 ) : δ 0.60-0.85 (m, 4: 2xCH 2 ) , 1.83 (m, 1: CH) , 2.40 (s, 3: CH 3 ) , 7.20-8.20: (6 aromatic protons), 9.45 (s, 1: NH) . EXAMPLE 15 Preparation of N.2.2-trimethyl-N-r5-methyl-3'- (tri luoromethyl) ri.1 ' -biphenyl!-2-yl1 -propanamide 0.8 g 2,2-dimethyl-N-[5-methyl-3'-(trifluoromethyl)- [1,1'-biphenyl]-2-yl]-propanamide was dissolved in 15 ml acetone, 0.8 g powdered potassium hydroxide added, and the mixture was energetically stirred wile adding 1 g iodomethane after which it was kept at reflux for 5 min. After cooling, the mixture was filtered, the filtrate concentrated in vacuo, 30 ml water added and the mixture extracted with ethyl acetate. The organic extracts were washed three times with brine, dried over magnesium sulfate and evaporated to dryness. The crude product was purified by chromatography on silica using 1:1 chlorobutane/ethyl acetate mixture as eluent to yield 0.6 g pure product as a light tan oil. X H NMR (CDCI 3 ) : δ 1.06 (s, 9: C(CH 3 ) 3 ), 2.40 (s, 3: CH 3 ) , 3.00 (s, 3: NCH 3 ) , 7.05-7.65 (7 aromatic protons) . EXAMPLE 16 Preparation of 2-nitro- '-(trifluoromethyl)-1.1 '-biphenyl A solution of 5 g (0.02 mol) meta-iodonitrobenzene, 6.8 g (0.022 mol) trimethyl [3-(trifluoromethyl)phenyl]- stannane, and 0.2 g palladium bis (triphenylphosphine) dichloride in 50 ml dry tetrahydrofuran was refluxed under nitrogen for 6 hrs. After cooling to room temperature, the reaction mixture was poured over 200 ml saturated sodium bicarbonate solution, stirred for 20 min, then extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulfate, filtered, and evaporated to dryness. The residue was chromatographed on silica using 1:3 chlorobutane/hexane mixture as eluent to yield 5.6 g pure product as a light tan oil. EXAMPLE 17 Preparation of '-(trifluoromethyl)- ' r1r '-biphenyl1-2-amine 5.4 g (0.02 mol) of 2-nitro-3'-(trifluoromethyl)- 1,1'-biphenyl was dissolved in 80 ml ethyl acetate, 5 ml acetic acid and 0.2 g 10% palladium on charcoal were added, and the mixture was hydrogenated at balloon pressure overnight. The catalyst was removed by filtration and the solution evaporated to dryness. The residue was dissolved in hexane, washed with 0.5 M sodium hydroxide solution, then brine, dried over magnesium sulfate, filtered, treated with charcoal, filtered, and evaporated to dryness. The residue was dried in a vacuum oven under nitrogen at 40°C to afford 4.5 g pure product as a light tan oil. EXAMPLE 16 Preparation of N- (2-boronophenyl)- 2.2-dimethylpropanamide A solution of 25.5 (0.1 mol) N- (2-bromophenyl)-2, 2- dimethylpropanamide in 300 ml dry ether and 60 ml dry tetrahydrofuran was cooled at -10°C under nitrogen and 137 ml (0.22 mol) 1.6M butyllithium in hexanes was added dropwise during 1 hr while maintaining the temperature below 0°C. After complete addition stirring was continued for 3 hrs on the cold bath after which the reaction mixture was transferred via cannula, under light nitrogen pressure, into a solution of 40 g (0.4 mol) trimethyl borate in 100 ml dry tetrahydrofuran, cooled at -10°C. The rate of addition was adjusted in such a way as to maintain the temperature below 0°C. After complete addition stirring was continued over night, allowing the cold bath to melt. The reaction mixture was evaporated to dryness, 300 ml 10% hydrochloric acid and 100 ml tetrahydrofuran added, and the mixture stirred at the room temperature for 3 hrs. Solvents were removed in vacuo and the residue was recrystallized from hot water. After drying in a vacuum oven overnight, 17.7 g (80%) of N-(2-boronophenyl)-2,2-dimethylpropanamide was obtained. EXAMPLE 19 Preparation of N- (3'-cyanofl.1 '-biphenyl!- 2-yl) -2.2-dimethylpropanamide A mixture of 9.1 g (0.05 mol) Λ-eta-bromobenzonitrile, 0.300 g palladium bis (triphenylphosphine) dichloride, and 15 ml gly e was stirred under nitrogen for 15 min., after which 13.3 g (0.06 mol) N- (2-boronophenyl)-2,2-dimethyl¬ propanamide was added, followed by a solution of 12.7 g (0.12 mol) sodium carbonate in 150 ml water. The reaction mixture was kept at reflux under nitrogen for 6 hrs. After cooling, 150 ml IN sodium hydroxide solution was added and the mixture was extracted with ethyl acetate. The organic extracts were washed twice with brine, dried over magneziu sulfate, and evaporated to dryness. The crude product was purified by chromatography on silica using chlorobutane/ethyl acetate 40:1 as eluent, to yield 10.6 g (76%) N-(3'-cyano[1,1'- biphenyl]-2-yl)-2,2-dimethylproρanamide, m.p. 178-181°C. EXAMPLE 20 Preparation of N-(5-bromo- '-cyanofl.1 '-biphenyl!- 2-yl)-2.2-dimethylpropanamide A solution of 6.7 g (0.042 mol) bromine in 15 ml glacial acetic acid was added dropwise, during 1 hr, to a solution of 8.4 g (0.3 mol) N-(3'-cyano[1,1'-biphenyl]-2- yl)-2,2-dimethylpropanamide and and 10.6 g (0.1 mol) sodium acetate in 50 ml glacial acetic acid. After complete addition stirring was continued for 6 hrs. The acetic acid was removed in vacuo, ice was added and the suspension was made basic with 10% sodium hydroxide and was extracted with ethyl acetate. The organic extracts were washed twice with brine, dried, and evaporated to dryness. The crude product was purified by chromatography on silica using chlorobutane/ethyl acetate 20:1 as eluent, to afford 9.85 g (92%) N-(5-bromo-3'- cyano[1,1'-biphenyl]-2-yl)-2,2-dimethylpropanamide as a viscous oil. -~S NMR (CDC1 3 ) : δ 1.05 (s,9: C(CH 3 ) 3 ), 7.15 (s,l: NH) , 7.4-8.1 (7H aromatic) . EXAMPLE 21 Preparation of N-(3'.5-diπyanofl.1'-biphenyl!- 2-yl)-2.2-dimethylpropanamide A mixture containing 3.6 g (0.01 mol) N-(5-bromo-3'- cyano[1,1'-biphenyl]-2-yl)-2,2-dimethylpropanamide, 1.1 g (0.012 mol) copper cyanide, 0.04 g copper sulfate, and 30 ml dry pyridine was kept at reflux, under nitrogen, for 72 hrs. After cooling, the reaction mixture was treated with 100 ml 10% ammonium hydroxide and extracted with ethyl acetate. The organic extracts were washed twice with 100 ml 10% ammonium hydroxide, then with 10% hydrochloric acid and brine, dried over magnezium sulfate, and evaporated to dryness. The residue was purified by chromatography on silica using chloro¬ butane/ethyl acetate 20:1 as eluent to afford 1.97 g (656%) N-(3',5-dicyano[1,1'-biphenyl]-2-yl)-2,2-dimethyl¬ propanamide, m.p. 54-59°C. EXAMPLE 22 Preparation of N-r5-ethynyl-3'- (trifluoromethyl)- r1, 1 '-biphenyl1-2-yl!-2-methylpropanamide 0.385 g (0.001 mol) N-[5-bromo-3'- (trifluoromethyl) - [1,1'-biphenyl]-2-yl]-2-methylpropanamide was added under nitrogen to a mixture of 15 ml triethylamine and 5 ml anhydrous acetonitrile, after which 0.2 g trimethyl- silylacetylene, 0.4 g triphenylphosphine, 0.2 g 10% palladium on charcoal, and 0.02 g copper iodide were added and the reaction mixture was refluxed for 18 hrs. After cooling, the catalyst was removed by filtration and the filtrates were diluted to 50 ml with ethyl acetate, washed with 50 ml 10% hydrochloric acid, then brine, dried over magnezium sulfate, and evaporated to dryness. The residue was purified by chromatography on silica using chlorobutane/ethyl acetate 40:1 as eluent. 0.350 g (90%) 2-methyl-N-[3'-(trifluoromethyl) -5-[trimethyl- silyl)ethynyl] [1,1'-biphenyl]-2-yl]-propanamide was obtained, m.p. = 145-149°C. 0.300 g 2-methyl-N-[3'-(trifluoromethyl)-5-[tri- methylsilyl)ethynyl] [1,1'-biphenyl]-2-yl]-propanamide was disolved in 5 ml absolute methanol, a solution of 0.04 g KOH in 2 ml water was added, and the mixture stirred at the room temperature for 4 hrs. The solvent was removed in vacuo, the residue taken in ethyl acetate and washed twice with brine, then dried over magnezium sulfate and evaporated to dryness. The residue was disolved in ether, treated with activated carbon, filtered, and evaporated, to afford 0.285 g (92%) N-[5-ethynyl-3'- (trifluoromethyl) [1,1'-biphenyl]-2-yl]-2-methyl¬ propanamide, m.p. = 108-111°C. Using the procedures outlined in Schemes 1-10 and Examples 1-22 of this section, the compounds of this invention including those listed in Tables 1-11 can be readily prepared by one skilled in the art. TABLE 1 -B ' Me Me H H H H H H H H H H Me H H H • H H H H H H H H H H H H H H Me H £' H H H H H H H H H H H H H H H H H H H H H H H H H H H Α H H H H £ H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H " Me H H H H H H H H H H H H H H H H H H £ £ α £- £' CF 3 H CF 3 H CF 3 H CF 3 H CF 3 H Cl H Cl H Cl H Cl H Cl H Cl H Cl H Cl H Cl H Cl H Cl H Br H Br H Br H Br H Br H Br H Br H Br H Br H Br H Br H Br H CN H CN H CN H CN H £ £ J £- £ CN H CN H CN H CN H CN H CN H NO2 H N0 2 H N0 2 H N0 2 H N0 2 H N0 2 H N0 2 H N0 2 H N0 2 H N0 2 H N02 H N0 2 H OCF3 H OCF 3 H OCF 3 H OCF 3 H OCF 3 H OCF3 H OCF 3 H OCF 3 H OCF 3 H OCF3 H OCF 3 H OCF3 H OCF3 H SCF3 H £' H H H H H H H H H H H H £ £ x £ J £' CF 3 Me CH 2 CH(C 2 H5)OCH3 H CF 3 Me CH(C 2 H 5 )CH 2 OCH 3 H CF3 Me CH 2 CH 2 SCH CH3 H CF3 Me CH CH 2 F H CF3 Me CH(CH 2 F) 2 H CF3 Me cyclobutyl H CF3 Me 2-Cl-σyclopentyl H £' H Me H H H H H H H H H H H H H H H Me H H H H H H H H H H H H H £ £' OCF 3 Me CH2CH 2 CH SCH 3 H OCF3 Me CH 2 CF 3 H OCF3 Me cyclopropyl H OCF3 Me CH 2 -cyclobutyl H OCF3 Me CH(CH3)-cyclopropyl H OCF3 Me C(CH 3 ) 2 -cyclopropyl H OCF3 Me CH 2 CH=CH 2 H OCF3 Me CH 2 C3r=CH 2 H OCF3 Me CH 2 C 6 H 5 H OCF3 Me 2-thiophenyl H OCF3 Et CH 3 H OCF3 Et CH(CH 3 ) 2 H OCF3 Et CH 2 CH 2 CH2θCH 3 H OCF3 Et CH2CH 2 C1 H OCF3 Et CH(CH 3 )CF 3 H OCF3 Et cyclopropyl H OCF3 Et CH -cyclobutyl H OCF3 Et CH 2 (2-Me-cyclopropyl) H OCF3 Et CH 2 CH=CH 2 H OCF3 Et CH 2 C(C1)=CH 2 H OCF3 Et CH 2 C 6 H 5 H OCF3 Et 2-thiophenyl H OCF 3 Pr CH(CH 3 ) 2 H OCF3 Pr CH 2 CH 2 SCH 3 H OCF3 Pr CH 2 CH 2 Br H OCF.- Pr CH(CH 3 )CF3 H OCF3 Pr cyclobutyl H OCF3 Pr CH(CH3)-cyclobutyl H OCF 3 Pr 2-pyrrolyl H OCHF2 Et CH(CH 3 )2 H OCHF2 Et CH 2 CH SCH3 H £' H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H £' H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H E* E' Me Me Me H H H H H H . H Me Me H H H H Me H H H H Me Me Me Me H H H H Me Me H £ E« £' CF 3 Me H CF 3 H Me CF3 H Me CF 3 Me Me CF 3 H Me CF 3 Me H CF 3 Me Me E E- 1 E- £' CF 3 Me H CF3 Et H Cl Me H Br Me Me CF3 Me H Cl Me H CF 3 Me H CF 3 Me H CF 3 Me Me 1&BI-E_≥ E E CF 3 Me CF3 Et Cl Me Br Me CF 3 Me O Cl Me O CF 3 Me NH CF3 Et NCH3 TABES g Σ E J E' CH(CH 3 ) 2 H C(CH 3 ) 3 Me C(CH 3 ) 2 Br H 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 Wettable Powders Typical solid diluents are described in atkins, et al.., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey, Typical liquid diluents and solvents are described in arsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual , Allured Publ. Corp., Ridgewood, New Jersey, 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. , Pesti cide Formulations, Washington, D.C., 1988, pp 251-259. Suspensions are prepared by wet-milling; see, for example, U.S. 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, December 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. 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. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. 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. 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 7. Example h High Strength Concentrate Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0% Example B Wettable Powder Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate . 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0% Example C Granule Compound 1 10.0% attapulgite granules (low volative matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0% Example D Extruded Pellet Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0% UTILITY Test results indicate compounds of this invention are active postemergence and preemergence herbicides. Many compounds in this invention are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops such as barley (Hordeum VUlgare) , corn (Zea mays) - cotton (Gossypium hirsutum. , rice (Oryza sat-jva) , sorghum (Sorghum bicolor) , soybean (Glycine max) and wheat (Triticum aestivum) . Grass and broadleaf weed species controlled include, but are not limited to, barnyardgrass (Echinochloa crusσalli. , bedstraw (Ga-L υm aparine) , blackgrass CAlopecurus yosuroides) , c-iickweed (Stel-Laria maci-ia.) , crabgrass (Pigitaria spp.), foxtail (Setaria spp.), lambsquarters (Chenopodi m spp.), velvetleaf (Abutilon theophrasti, . wild buckwheat (Polyσonum convolvulus) and wild oats (Avena fatua) . These compounds also have utility for weed control of selected vegetation in specified areas such as around storage tanks, parking lots, highways, and railways; in fallow crop areas; and in citrus and plantation crops such as banana, coffee, oil palm, and rubber. Alternatively, these compounds are useful to modify plant growt . Effective amounts of the compounds of this invention are 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, effective amounts of compounds are applied at rates from 0.01 to 20 kg/ha with a preferred rate range of 0.02 to 4 kg/ha. Although a small number of compounds show slight herbicidal activity at the rates tested, it is anticipated these compounds are herbicidally active at higher application rates. One skilled in the art can easily determine effective application rates necessary for desired level of weed control. 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-di-2-propenylacetamide, 2- chloroallyl diethyldithiocarbamate, chloramben, chlor romuron, chloridazon, chlorimuron ethyl, chlormethox nil, 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-l,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, dy ron, endothall, S-ethyl dipropylcarbamothioate, esprocarb, ethalfluralin, ethametsulfuron methyl, ethofumesate, fenac, fenoxaprop, fenuron, salt of fenuron and trichloroacetic acid, flamprop, fluazifop, fluazi op-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, methabenz- thiazuron, 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, piclora , 5-[2-chloro-4- (trifluoromethyl)phenoxy]-2-nitroacetophenone oxime-0- 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, trichloro¬ acetic acid, tebuthiuron, terbacil, terbuchlor, terbuthylazine, terbutol, terbutryn, thifensulfuron methyl, thiobencarb, tri-allate, trialkoxydim, triasulfuron, tribenuron methyl, triclopyr, tridiphane, trifluralin, trimeturon, (2, 4-dichlorophenoxy)acetic acid, 4- (2,4-dichloroρhenoxy)butanoic acid, vernolate, and xylachlor. Herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. Test procedures and results follow. Selective herbicidal properties of the subject compounds were discovered in greenhouse tests as described below. TABLE 7 £' m.p. f°C) H 97-100 H 110-113 H 72-77 H 142-145 H 151-154 H 108-110 H 71-76 H 103-106 H X H NMR (CDCI3) : 6 1.05 (s,9: C(CH3) 3 ), 2.40 (s,3: CH3), 7.05- 7.65 (7H aromatic) 112-114 95-97 78-80 145-147 81-84 111-114 106-108 139-141 89-91 85-87 128-130 ,): δ 1.06(s,9: C(CH 3 )3) A 2.40 (s,3: CH3), 3.00 (s,3: NCH3), 7.05-7.65 (7 aromatic H) £' m.p. ( °C ) H 115-117 H 79-81 H 101-103 H 132-134 H 106-108 H 115-117 H 99-101 CH 3 71-73 CH 3 X H NMR (CDCI3) : δ 0.6 (m,2: CH 2 ), 0.75 (m, 1: CH) , 1.0 (m, 1 : CH) , 1.3 (t,3: CH3), 1.45 ( , 1: CH), 2.75 (q, 2: CH2), 2.95 (s,3: CH3), 7.25- 7.6 (7H aromatic) 75-77 136-138 162-163 76-78 122-124 119-121 76-78 100-102 112-114 74-76 114-116 98-100 95-97 m.p. (°C) 78-80 X H NMR (CDCI3) : δ 1.3 (t,3: CH3), 1.6 (s,3: CH3), 1.8 (s,3: CH3), 2.75 (q,2: CH 2 ), 3.1 (s,3: CH3), 7.2-7.6 (7H aromatic) 102 Br Et CH 3 H 84-86 103 CF3 Me CHF 2 H X H NMR (CDCI3) : δ 2.4 (s,3: CH3), 5.9 (t,l: CHF ), 2.75 (q,2: CH 2 ), 3.1 (s,3: CH3)., 7.1-8.1 (7H aromatic & NH) 1.1 (s Λ 8: t-Bu), 2.4(s,3: CH3), 6.9 (t,l: CHF2), 3.1 (s,3: CH3), 7.0-8.1 (7H aromatic & NH) 130 Cl Me 1-Me-cyclopropyl H 75-77 m.p. CO 138-140 153-155 X H NMR (CDCI3) : δ 0.6 (t,2: CH 2 ), 1.1 (s,3: CH 3 ), 1.2 (t,2: CH ), 2.4 (s,3: CH3), 7.0-8.1 (7H aromatic & NH) 145-147 74-76 115-117 116-118 74-76 122-124 104-106 111-112 112-113 115-116 152-153 107-108 83-85 102-104 148-150 102-104 155-157 107-109 128-130 89-90 123-124 130-132 130-131 116-117 163-165 m-p. ( °C) 114-115 113-114 89-90 91-93 100-102 127-128 126-127 137-138 234-239 226-228 157-158 145-147 136-138 152-153 " 132-134 124-125 105-109 X H NMR (CDCI3) : δ 0.6(t,2: CH2), 1.1 (s,3: CH 3 ),1.2(t,2: CH2), 2.35(s,3: CH 3 ), 2.4 (s,3: CH 3 ), 7.05-8.2(7H aromatic & NH) 1-Me-cyclopropyl CH(CH 3 ) 2 cyclopropyl CH(CH 3 ) 2 cyclopropyl 2-Me-cyclopropyl 2-Me-cyclopropyl 2-Me-cyclopropyl 2-Me-cyclopropyl No . E £ J £ J £' m.p. (°C. 204 SCHF2 Me 2-Me-cyclopropyl H 98-100 205 CF3 Br 1-Me-cyclopropyl H 85-87 208 CN Et cyclopropyl H 167-168 209 CF3 Br 1-Me-cyclopropyl H 138-140 210 CF3 Br CH=C (CH3) 2 H 110-112 211 OCF2 Me CH (CH 3 ) 2 H 97-98 212 OCF2 Me CH (CH 3 ) 2 COCH(CH 3 ) 2 X H NMR (CDCI3) : δ 0.8 (m, 4: 2xCH 2 . , 0.9(m, 4: 2xCH 2 ), 2.0 (m,2: 2xCH) , 2.4(s,3: CH3), 6.7 (t,l: CHF 2 ),7.1- 7.4 (7H aromatic) 214 OCF2 Me 1-Me-cyclopropyl X H NMR (CDCI3) : δ 0.6(t,2: CH 2 ), 1.1 (s,3: CH 3 ),1.2(t,2: CH 2 ), 2.4(s,3: CH3), 6.8(t,l: CHF 2 ),7.05-8.2(7H aromatic & NH) 163-164 158-159 178-181 X H NMR (CDCI3) : δ 1.05 (s,9: C(CH 3 )3), 7.15 (S,l: NH) , 7.4-8.1 (7H aromatic) 221 CF3 Br C(CH3)2θCOCH 3 H H NMR (CDCI3) : δ 1.6 (s,6: 2XCH3), 1.7 (s,3: COCH 3 ), 7.2-8.2 (7H aromatic & NH) 222 OCF3 Br C(CH 3 )3 X H NMR (CDCI3) : δ 1.05 (s,9: C(CH 3 ) 3 ), 7.4-8.25 (7H aromatic δ NH) £ £' m.p. CC) 223 SCF 3 H C(CH 3 )3 H 69-75 224 CN Br CH(CH 3 )2 H 165-168 225 SCF 3 Br C(CH 3 )3 H H NMR (CDCI3) : δ 1.05 (s,9: C(CH 3 )3), 7.2 (s,l: NH), 7.25-8.2 (7H aromatic) 108-111 54-59 133-135 165-170 124-127 137-138 115-116 91-92 99-100 142-143 168-169 2-~ E E J E y m-p. CO 25 CF3 Me CH3 H X H NMR (CDCI3) : < 2.38 (s,3: CH 3 ) , 3.65 (s,3: CH 3 ), 6.28 (s, 1: NH), 7.02-7.90 (7H aromatic) m.p. CO 83-85 H NMR (CDCI3) : δ 2.4 (s,3),4.8 (s,2: CH 2 ), 6.5 (s,l: NH), 7.05-7.80 (7H aromatic) CF3 Me CH 2 CH3 H NMR (CDCI3) : δ 1.22 (t,3: CH 3 ), 2.32 (5,3: CH3), 4.2 (q,2: CH 32 ) , 6.28(s, 1: NH), 7.02-7.90 (7H aromatic) 38-40 51-53 92-94 96-98 86-88 X H NMR (CDCI3) : δ 0.9 (t,3: CH3), 1.25 (t,3: CH3), 1.6 (m, 2: CH 2 ), 2.6 (m,2: CH ), 4.1 (t,2: CH 2 ), 6.3 (S,l: NH), 7.0-7.9 (7H aromatic) 85-87 X H NMR (CDCI3) : δ 0.9 (d, 6: 2XCH3), 1.25 (t,3: CH3), 1.9 (m,1: CH) , 2.6 (m,2: CH 2 ), 3.9 (d,2: CH 2 ), 6.4 (s,l: NH), 7.0-7.9 (7H aromatic) N0 2 Et H X H NMR (CDCI3) : δ 0.9 (d, 6: 2XCH3), 1.25 (t,3: CH3), 1.9 (m,l: CH) , 2.6 (m,2: CH 2 ), 3.9 (d,2: CH 2 ), 6.3 (s,l: NH), 7.0-8.3 (7H aromatic) -N- -, £ E £ J m.p. CO 87 Cl Me CH 2 CH 3 H H NMR (CDCI3) : δ 1.25 (t,3: CH 3 ), 2.3 (s,3: CH3), 4.2 (q,2: CH 2 ), 6.3 (s,l: NH), 7.0-8.0 (7H aromatic) 88 CF 3 Et CH 2 CH 3 H 46-48 95 Cl Et CH 2 -cyclopropyl H X H NMR (CDCI3) : δ 0.3 (m,2: CH2), 0.6 (m,2: CH 2 ), 1.1 (m,l: CH), 1.25 (t,3: CH3), 2.6 (q,2: CH 2 ), 3.9 (d,2: CH 2 ), 6.3 (s,l: NH), 7.0-8.0 (7H aromatic) 62-64 X H NMR (CDCI3) : δ 0.95 (t,2: CH 3 ), 1.6 (m,2: CH 2 ) , 2.6 (t,2: CH 2 ), 3.7 (s,3: OCH3), 6.35 (s,l: NH), 7.0-7.9 (7H aromatic) 76-78 46-48 X H NMR (CDCI3) : δ 0.3 (m,2: CH 2 ), 0.6 (m,2: CH 2 ), 1.1 (m,l: CH), 2.4 (t,3: CH3), 3.95 (d,2: OCH ), 6.3 (S r l : NH), 7.0-7.9 (7H aromatic) 105 CF 3 Me benzyl H 56-58 106 Cl Me benzyl H X H NMR {CDCI3) : δ 2.35 (s,3: CH3) , 5.2 (s,2: CH 2 ), 6.45 (s,l: NH), 7.0-8.0 (7H aromatic) 106-108 77-79 H 84-86 H 51-53 H 111-113 H 65-66 H 92-94 H 141-143 H 56-58 H 50-52 H 61-63 H 66-68 H 104-105 H 100-102 H 84-85 H 73-74 H X H NMR (CDCI3) : δ 0.9 (d, 6: 2xCH 3 ), 1.2 (t,3: CH3), 1.9 ( , 1 : CH) , 2.6 (t,2: CH 2 ), 3.9 (d, 2: OCH 2 ), 6.3 (S,l: NH), 7.0-7.9 (7H aromatic) 177 CH3 Me CH(CH3) 2 H X H NMR (CDCI3) : δ 1.2 (d, 6: 2XCH3), 2.35 (s,3: CH3) , 2.4 (s,3: CH3) , 5.0 (m, 1: OCH), 6.3 (s,l: NH) , 7.0-8.0 (7H aromatic) 178 CH3 Me CH 2 CH(CH3) H X H NMR (CDCI3) : δ 0.9 (d, 6: 2XCH3), 1.95 (m, 1: CH) , 2.35 (s,3: CH3) , 2.4 (s,3: CH3), 3.9(d,2: OCH 2 ), 6.55 (s,l: NH), 7.0-8.0 (7H aromatic) 199 CH3 CN CH(CH 3 )2 H 68-69 200 CF3 Br CH(CH 3 ) 2 H 97-98 230 OCF 3 Br CH(CH 3 ) 2 H 81-88 2 LSL-2. TABLE 10 m.p. CO 35 185-187 36 129-131 37 125-127 38 147-148 TABLE 11 240 m.p . =65-70 °C R=iPr 241 m.p.=88-94°C 243 m.p.=102-106°C Et 242 m.p.=55-60°C 244 m.p.=106-114°C 245 m.p.=110-113°C TEST A Seeds of barnyardgrass (Echinochloa crus-galli ) , cheatgrass (Bromus secalinus) , cocklebur (Xanthium pensylvanicum) , crabgrass (Digi taria spp.), giant foxtail (Setaria faberii ) , morningglory ( Ipomoea spp.), sorghum (Sorghum bicolor) , velvetleaf (Abutilon theophrasti ) , and wild oat (Avena fatua) were planted into a sandy loam soil and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated postemergence with test chemicals. Plants ranged in height from two to eighteen cm and were in the two to three leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately eleven days, after which all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized ~ι Table A, are based on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test results. TABLE A COMPOUND TABLE A COMPOUND Rate 2000 g/ha 242 Rate 2000 g/ha 242 POSTEMERGENCE PREEMERGENCE Barnyardgrass 8 Barnyardgrass 10 Cheatgrass 5 Cheatgrass 9 Cocklebur 0 Cocklebur 0 Crabgrass 9 Crabgrass 10 Giant foxtail 7 Giant foxtail 10 Morningglory 0 Morningglory 1 Sorghum 6 Sorghum 10 Velvetleaf 0 Velvetleaf 6 Wild oats 4 Wild oats 10 TEST B 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) , lambscjuarters ( Chenopodium album) , morningglory (Jpojπoea hederacea) , rape (Brassica napus) r 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 (C pe-rus 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 f om 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 means no test result. Table B COMPOUND Rate 2000 g/ha 50 80 84 107 108 110 118 128 144 145 PREEMERGENCE Barley 1 0 2 0 3 2 0 0 5 1 Barnyardgrass 10 0 5 7 8 9 0 6 10 7 Bedstraw 7 2 4 8 9 5 0 8 10 Blackgrass 8 2 4 7 10 7 0 6 10 3 Cheatgrass 3 0 5 3 6 1 1 6 10 4 Chickweed 9 2 8 10 9 10 9 10 Cocklebur 0 0 0 4 0 2 Corn 4 0 0 Cotton 0 0 0 3 1 3 0 0 10 Crabgrass 9 7 7 8 10 10 3 8 10 Giant foxtail 10 0 9 4 10 10 0 10 10 Lambsquarter 10 2 9 9 9 99 7 0 9 10 Morningglory 6 0 1 5 10 3 0 2 10 Nutsedge 0 0 0 0 3 Rape 8 0 10 10 10 Rice Sorghum 10 0 3 Soybean 0 0 0 0 0 9 Sugar beet 10 0 10 10 Velvetleaf 1 0 2 10 10 0 5 10 Wheat 0 0 2 0 3 Wild buckwheat 3 0 0 1 7 Wild oat 6 1 6 3 8 Table B COMPOUND Rate 1000 g/ha 51 52 53 54 56 57 58 59 60 61 62 63 64 65 66 67 69 70 71 72 73 74 75 76 77 78 79 81 POSTEMERGENCE Barley 1 2 2 2 2 2 0 2 0 1 0 0 1 0 1 0 0 1 0 1 0 2 0 1 1 0 1 2 Barnyardgrass 7 5 2 7 9 2 2 9 2 2 3 2 1 1 2 2 0 4 0 3 2 6 3 5 3 0 2 4 Bedstraw 5 8 6 7 9 3 4 7 4 5 3 2 4 3 5 5 0 5 5 6 2 5 7 6 6 4 7 9 Blackgrass 2 3 3 2 5 2 2 4 1 2 1 1 1 1 3 2 0 1 1 2 1 5 2 3 3 0 3 5 Cheatgrass 1 2 2 2 5 2 1 2 1 1 1 0 1 2 4 4 0 1 0 1 0 1 0 1 3 0 3 4 Chickweed 7 4 7 5 7 2 3 5 3 4 2 1 3 1 6 3 0 4 3 6 1 3 2 2 4 3 4 5 Cocklebur 3 5 5 6 7 5 3 7 3 5 0 2 3 0 3 1 0 5 1 4 0 2 3 2 2 1 3 1 . Corn 2 5 3 2 3 3 2 3 2 3 2 1 2 0 1 1 0 1 1 1 1 4 2 3 2 0 2 1 Cotton 9 10 9 9 9 8 9 9 8 10 4 1 3 1 5 1 0 7 2 3 0 6 1 1 2 1 2 4 Crabgrass 7 7 6 - 9 3 6 ' 8 6 4 5 2 3 2 5 1 0 2 3 3 4 5 2 3 5 1 4 8 Giant foxtail 3 4 4 7 5 3 4 9 3 4 3 2 4 2 3 1 0 2 0 2 4 4 2 2 6 1 3 2 Lambsquarter 9 9 8 8 9 9 0 9 - 9 1 3 2 2 6 2 0 7 - 10 1 2 3 7 9 - - 4 Morningglory 7 5 6 5 9 7 1 9 4 2 1 1 1 2 3 2 2 5 4 5 3 7 7 4 4 2 5 5 Nutsedge 0 0 0 1 2 0 0 0 0 0 - 0 - 0 - 0 0 0 0 0 0 0 0 0 1 0 0 0 Rape 4 4 7 8 8 8 0 8 3 6 1 3 6 1 5 2 0 7 1 8 1 1 8 1 7 0 9 1 Rice 2 2 1 1 3 3 1 4 3 4 1 0 2 0 1 1 0 1 0 1 0 4 2 1 2 0 2 0 Sorghum 1 1 1 1 3 2 1 2 2 3 2 0 1 2 1 1 0 0 1 2 0 2 1 0 2 0 1 0 Soybean 3 7 1 2 6 3 2 6 4 4 1 1 2 0 2 1 1 4 2 3 1 6 5 3 5 1 5 5 Sugar beet 9 8 9 9 9 9 2 9 7 5 1 6 6 3 5 5 0 9 6 7 1 8 6 7 9 1 8 8 Velvetleaf 7 7 6 7 7 0 0 7 3 3 3 2 3 2 3 1 2 3 2 3 0 3 1 2 4 0 7 3 Wheat 1 2 2 2 2 0 0 1 1 1 1 0 1 0 2 2 0 1 0 1 1 0 0 0 1 0 1 2 Wild buckwheat 3 7 6 8 8 2 7 3 1 5 2 1 3 1 5 1 2 - 5 5 0 2 7 2 4 2 2 5 Wild oat 1 2 1 3 4 0 1 2 1 3 2 0 1 1 3 1 0 2 2 3 1 5 1 1 3 0 1 2 Table B COMPOUND Rate 1000 g/ha 82 83 85 86 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 109 111 112 POSTEMERGENCE Cotton Cocklebur 7 3 5 1 5 5 5 2 7 2 7 4 5 5 5 9 5 7 2 4 1 Corn 8 6 2 2 2 2 7 9 9 3 8 2 8 7 2 8 3 6 4 1 0 Cotton 5 3 3 4 3 4 2 5 2 - 9 7 8 9 9 8 9 10 9 8 5 Crabgrass 8 7 5 5 3 3 7 8 9 2 8 3 7 9 3 9 2 6 4 1 1 Giant foxtail 9 6 5 3 3 3 9 9 9 3 9 3 8 8 3 9 2 6 4 1 1 Lambsquarter 6 3 5 4 8 6 7 7 8 6 9 7 8 8 8 7 6 8 7 3 2 Morningglory 9 5 6 4 6 5 7 7 9 1 7 3 5 6 5 4 4 7 3 5 3 Nutsedge 7 0 1 0 0 0 5 - 7 0 - 0 - 3 3 0 0 0 0 0 0 Rape 6 8 7 0 6 4 6 9 9 8 9 7 6 7 9 8 5 9 5 4 0 Rice 7 1 2 2 4 3 6 7 8 2 9 1 6 5 3 3 2 2 2 1 0 Sorghum 5 2 0 3 2 0 5 9 8 2 7 1 8 7 2 8 2 3 1 1 0 Soybean 4 1 3 2 6 4 6 7 9 9 10 7 7 5 7 4 5 7 2 2 1 Sugar beet 8 9 8 6 9 9 9 9 10 8 10 8 9 10 10 10 9 10 6 7 1 Velvetleaf 6 4 3 7 7 7 9 2 5 2 5 4 4 7 6 4 5 5 2 1 1 Wheat 3 '2 0 0 1 1 4 8 9 1 7 1 3 4 2 3 1 3 0 1 0 Wild buckwheat 9 3 3 3 4 7 4 9 9 8 9 6 8 7 6 6 4 5 5 5 3 Wild oat 6 4 0 0 1 1 4 8 9 4 7 3 6 7 3 5 2 4 2 2 0 w oo oo co co σi r- rt σ to -n σ oo rt cn rt w .— σi to w oo w t rt β) n 01 0 01 0 βl O. Ol 01 0 01 01 ^ > (7I C0 01 01 0 C 91 01 0 to w σi σi oo σi co σ to σ σi σi σi σ cJi co co σ σi oo o co co σi cri to rt oo σ vo co co m r- o crι σι cn σι o r- «a , «3' t^ o oo cs oo r- to r. r. o w σ σι - co m -n .^ o co oo r- ι-!. w co -n *)' oo o oo co r- '<a « to rt r- -i rt r- I w u. (θ cn . cθ («) c s | iΛ N >j n fo <f Λ θ. H co « rt co cM r~ O f CO H H H I rt t~- CO W C W O CNl rt rt rt C W O W rt ιn r-i vo rt O W rt ^' CO rt m W W CO tO O 'a' O rt r- CJl CO CVl M' rt m rt rt *3 , t-- oi co cv j -n to ιo W O rt H ?l C0 -. l»i m i-i (M 0S P. N 00 t- O -l N N <J O V N 1 N rt w co o w rt r~ m w cn w w ι^ -n o vo o o -n co w w co co m τ-i p- - , co w σ co 01 o 01 01 I co σ o σ σ o σι *tf σ σ. σι co o cr. r~- oι σι τ-i " rt rt r. 03 is oi o oi oo I oo σi o σi σi σi σi m r- co σi r- o σi σi σi σi rt rt rt r- rt W I rt rt -n W W σ lΛ rt in O O rt O rt ^' CO m rt CVl rt rt to W tO CO CO W I O VO OO lθ r- W CO W W O tO rt W rt C '3' CO τ-i W o o r^ ^r o r o tn o co i- βi oo m σi ^ to σt o o αo ^ 1 rt rt rt O rt 'W O O 'fl' rt rt CO rt O CO rt rt W O O t-. W O O CO O rt O rt I W rt I W rt OO W W in ^ O O O rt CO rt rt O CO O co A a O H \ U O •rl M ι Cn 2 cfl cfl φ 14 ω 14 CO O 4-1 4-1 O 4-1 14 o U tn co co O U CO M U H φ cd o α. τl S cθ cθ Φ 3 CO O O tn φ φ Φ 4J to O H M CO M Φ -Q π) "w 3 tn C Λ H 3 CO rt S t CO 14 Oi O S Φ C &• C -0 CO 4-1 Λ O <D g 111 , il ϋ 4J M H O Ol -U CO -H Λ .. Φ . M . φ . 4.-1 rt φ £H H C W O cO O -i-! C 4 Λ α Λ fi co φ Φ σι Δ tO > cθ , O O -Q 4- ) C M I4 , σ cO Φ -H O 4J CO Cθ B >4 4J C-. O l4 01 H Φ H H co cq o co cfl Φ H -C -C o o o -H ra o s cq -H O O S Φ -α -H -H EH α α4 CQ ca ca m u u u u u u c-5 j ∑ z α β . co w co > s: s: S Chickweed 9 9 7 8 4 3 4 3 3 3 4 5 3 2 8 8 8 3 6 6 8 7 Cocklebur 3 6 2 2 3 3 4 3 2 2 3 3 4 1 4 4 7 1 7 7 7 . 8 Corn 7 6 1 7 5 7 5 3 1 1 6 7 2 2 7 7 6 1 6 5 2 8 Cotton 8 10 8 7 9 9 9 - 7 9 10 9 9 10 10 10 10 8 10 10 10 9 Crabgrass 6 4 2 1 3 3 4 2 2 2 9 9 5 6 9 9 6 3 7 8 6 9 Giant foxtail 6 2 1 1 2 5 5 1 1 1 9 9 2 2 7 9 6 3 9 8 6 9 Lambsquarter 9 9 7 3 5 6 6 2 6 8 8 8 9 7 9 7 9 6 6 8 9 10 Morningglory 8 9 3 3 8 9 8 2 3 6 6 7 6 2 8 8 8 5 10 7 6 9 Nutsedge 2 2 0 0 2 2 2 0 0 0 5 3 1 0 2 4 2 2 3 3 0 - Rape 9 9 4 3 8 0 0 8 7 4 7 7 5 3 6 5 5 2 9 8 9 10 Rice 3 0 0 1 2 4 6 1 1 0 3 4 1 0 3 3 4 0 4 2 2 8 Sorghum 6 2 0 1 3 4 2 1 0 1 3 6 2 1 7 6 6 1 6 3 2 6 Soybean 8 8 4 7 7 7 6 4 5 4 7 7 6 4 8 6 8 2 9 5 7 9 Sugar beet 10 9 8 9 8 8 9 7 6 5 9 10 7 3 10 9 9 3 10 9 9 9 Velvetleaf 3 6 2 2 7 4 3 2 1 1 3 5 2 4 7 6 9 5 8 7 8 7 Wheat 5 2 0 0 1 0 1 3 0 1 1 0 0 0 2 1 2 1 3 2 2 4 Wild buckwheat 8 10 2 5 6 6 3 4 7 6 6 2 2 2 6 5 9 3 6 7 6 9 Wild oat 7 4 0 3 1 2 7 1 0 2 3 2 0 0 5 9 4 2 6 3 3 8 co r~ oo to co to r- ιn t~- w co r~ co rt σ w w -n o co w r- -n to w w t~ in co to m w r- W '<a* r- '<a' rt w w rt co co w w ro co 01 ιn c! θi c^ m σι r- t~ σι σι σι σ. σi rt co co -n σ! σ! r- -a' σι co Ol co «a , σ o m ^i' σ «a , to o σι σ σι r- en r- >-i' "si' r- o oo co oo vo O rt rt rt W rt C0 *l' V0 C0 C0 C0 W r- W C0 l- -3 , O *J , rt rt -n f-- W W .- W O τ-i w w co cvj w co w w -n w w vo to o vo rt rt co oo w w w co O O U o co -n vo «3 , co r~ w co σ! W "β , w vθ rt w w w to -3< co c r~ co O τ-\ Ol © O CO O O CO rt O W rt O W 'tf O O O O W O W O W O 00 00 W W W W rt «3' rt rt tO W O CO CO O W rt rt W «3' W W m rt 00 to oo oo ^ , co t-- vo oo vo cn r~ oo '3' rt oo ^i< co -^ cJ r- «3< to to 03 cfl 4-1 A a co rt CO "--. U co -. M t φ tn 2 tβ cfl φ M A a M O CO 4-> 4-1 O 5 o CD Oi co co ~~ U CO 14 M rt Φ CO X o o- •σ s co co φ s n o ca O Φ φ φ O 4-1 a M Cfl M M φ A CO Η 3 3 OOli OOli 6 C A H 3 CO 3 cfl 4-1 a O φ .. Φ >, -U -4 4 4J ΛS rt O & - rl 4.-l W - c Ό r. φ Λ Φ Φ -1 r-i Φ E4 rt C t0 O c0 O -i-! C 4J Λ C -g C C0 Φ Φ en Λ c0 > c0 O , α A 4J C M M τ) cfl φ -H O M 4J cfl cfl g M 4J Q < O M ι en rt φ rt H cfl cq θ cfl c0 Φ rt -C Λ O O O M -r ffl θ 3 cfl -rj θ O 3 Φ -C -H -r. £H c-. c-4 CQ ffl m eQ U θ U U U θ H4 S 2 « ά! co co co > ~~ ~z ~ s Table B COMPOUND Rate 1000 g/ha 4 5 6 7 9 10 11 14 17 18 19 21 22 23 24 26 28 29 30 31 32 33 39 40 41 45 46 47 49 PREEMERGENCE Barley 0 9 0 0 0 0 1 0 1 3 1 8 1 3 0 7 0 0 6 0 3 0 6 0 0 7 0 0 0 Barnyardgrass 5 10 0 9 1 0 3 10 9 10 10 10 7 10 1 10 3 3 10 8 10 8 10 0 0 10 0 3 9 Bedstraw 8 10 0 9 0 0 9 8 8 9 2 10 2 9 0 9 9 0 10 1 9 5 9 0 0 10 1 3 8 Blackgrass 2 10 0 5 1 0 8 9 10 10 10 10 6 9 0 10 5 3 10 4 9 5 10 0 0 10 3 6 9 Cheatgrass 0 10 3 5 0 0 3 2 5 10 4 10 3 7 0 10 1 2 10 1 6 2 10 0 0 10 1 2 3 Chickweed 7 10 2 9 0 - 5 8 1 9 9 9 7 - 0 10 5 2 10 1 10 4 9 0 3 9 1 8 9 Cocklebur 0 1 0 0 0 0 - 2 - 2 1 1 1 0 0 9 0 0 3 - 2 2 2 2 0 - 0 0 0 Corn 3 7 0 1 0 0 0 6 0 8 4 7 4 1 0 7 0 0 5 0 5 0 4 0 0 5 2 0 3 Cotton 0 8 0 0 0 0 0 0 2 9 2 10 0 1 0 1 0 2 3 0 1 0 0 0 0 1 0 1 0 Crabgrass 10 10 0 10 3 6 10 10 10 10 10 10 9 10 7 10 9 8 10 10 10 10 10 2 2 10 8 9 10 Giant foxtail 10 10 0 10 5 3 10 10 10 10 10 10 10 9 1 10 9 9 10 10 10 10 10 1 2 10 3 10 10 Lambsquarter - 10 0 9 0 0 9 10 2 10 - 10 - - - 10 - 2 10 - - 9 10 0 0 9 - - - Mo ningglory 2 10 0 4 0 0 1 8 0 9 8 10 2 0 1 10 0 2 10 0 7 2 2 0 0 9 0 1 2 Nutsedge . - 3 0 0 - 0 0 6 0 5 2 8 0 1 - 10 0 0 2 0 0 0 0 3 0 4 0 0 0 Rape 5 10 0 10 0 0 3 9 3 9 9 10 0 0 0 10 0 1 10 1 7 4 10 0 0 10 1 3 10 Rice 1 8 0 0 0 0 0 7 0 8 3 6 0 0 0 4 0 0 4 0 3 0 1 0 0 1 0 1 1 Sorghum 1 8 0 1 0 0 0 8 Soybean 6 8 0 0 0 0 0 5 Sugar beet 9 10 2 10 0 0 9 10 Velvetleaf 4 10 0 8 0 0 0 6 Wheat 0 9 0 1 0 0 2 1 Wild buckwheat 9 10 - - 0 0 - 7 0 10 2 10 3 4 0 10 0 0 10 1 8 2 9 0 0 10 1 3 Wild oat 2 10 1 2 0 0 7 8 7 10 8 10 5 6 0 10 2 2 10 1 9 5 10 0 0 10 0 2 Table B COMPOUND Rate 1000 g/ha 51 52 53 54 56 57 58 59 60 61 62 63 64 65 66 67 69 70 71 72 73 74 75 76 77 78 79 81 PREEMERGENCE Barley 0 2 0 2 5 0 0 2 0 0 0 0 0 0 0 0 0 2 1 1 0 1 0 0 0 0 3 2 Barnyardgrass 9 7 2 9 10 4 2 10 2 2 0 1 0 0 0 0 0 8 6 9 1 9 6 9 8 1 10 9 Bedstraw 2 3 2 6 9 1 2 8 0 6 0 0 0 0 1 0 0 9 0 6 0 7 5 9 9 0 6 6 Blackgrass 8 10 0 8 10 6 2 9 1 6 0 2 2 0 1 0 1 7 1 6 1 8 9 6 6 0 9 9 Cheatgrass 3 7 0 2 10 2 3 8 1 2 0 1 2 0 0 0 0 6 3 4 1 4 3 6 5 0 8 7 Chickweed 5 6 0 6 9 1 9 9 1 6 0 0 5 0 3 0 0 9 9 7 3 9 8 9 10 0 10 9 Cocklebur - 0 0 0 0 2 3 2 0 0 0 0 0 0 0 0 - 0 0 - 0 0 0 1 1 0 0 0 Corn 1 2 0 3 4 0 0 3 .0 0 3 0 0 0 0 0 0 0 3 1 2 5 4 4 3 0 4 2 Cotton 0 0 0 0 1 0 - 2 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 Crabgrass 10 10 6 10 10 9 8 8 7 10 7 2 5 3 0 0 3 9 8 9 7 10 9 9 10 0 10 9 Giant foxtail 10 10 6 10 10 9 8 10 8 9 7 7 5 1 0 0 0 9 1 10 8 10 9 10 9 3 10 8 Lambsquarter 9 9 0 9 10 8 0 9 0 9 - 0 - 0 - 0 0 8 3 9 0 9 9 9 9 0 10 9 Morningglory 1 2 1 0 5 0 1 6 0 0 1 0 0 0 0 0 0 0 2 0 1 6 4 8 8 0 0 1 Nutsedge 0 0 0 0 0 9 0 4 0 0 0 - 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 Rape 2 2 0 2 9 2 0 2 1 4 0 0 4 0 3 0 0 3 0 5 0 5 4 0 7 0 5 0 Rice 0 0 0 0 1 0 0 1 1 0 0 0 0 0 0 0 0 0 3 0 0 2 0 0 3 0 2 0 Sorghum 3 2 0 1 6 0 0 6 0 0 0 0 1 0 0 0 0 2 0 1 1 5 0 5 6 0 3 2 Soybean 0 0 0 0 1 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 3 1 0 3 0 0 0 Sugar beet 9 8 3 8 9 7 0 10 0 9 - 2 5 0 3 0 0 9 2 8 2 10 9 9 9 0 9 9 Velvetleaf 0 0 1 2 8 0 0 10 0 3 1 0 0 0 0 0 0 2 1 2 0 10 8 9 9 0 3 6 Wheat 0 1 0 0 4 0 0 3 0 0 0 0 0 0 0 0 0 1 0 0 0 1 2 1 1 0 2 1 Wild buckwheat 2 6 2 8 9 0 0 0 0 2 0 0 3 0 2 0 0 2 2 5 0 7 4 1 10 0 8 5 Wild oat 7 9 1 5 10 2 2 9 2 1 0 1 0 0 0 0 3 5 8 1 1 7 3 3 5 0 5 8 Table B COMPOUND Rate 1000 g/ha 82 83 85 86 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 109 111 112 PREEMERGENCE Barley 2 2 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 2 0 0 3 2 4 Barnyardgrass 3 5 0 1 9 0 1 0 2 0 0 0 0 0 4 0 0 3 0 1 9 2 0 , 9 10 9 Bedstraw 5 9 0 2 9 0 2 0 2 1 3 0 0 - 0 0 0 5 0 0 9 0 0 10 9 6 Blackgrass 7 9 0 2 10 1 5 0 3 0 0 0 0 0 2 0 0 7 0 0 9 0 0 10 9 8 Cheatgrass 6 8 2 0 10 0 2 0 2 0 0 - 0 0 3 0 0 7 0 1 8 0 0 8 7 4 Chickweed 7 10 0 0 9 0 2 0 2 0 0 0 0 0 - 0 0 3 0 - 6 0 0 10 10 9 Cocklebur 0 5 0 0 - 0 0 0 0 0 - 0 0 0 0 0 0 - 0 0 1 0 4 6 4 . 7 Corn 0 3 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 3 0 0 9 8 6 Cotton 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 1 0 - - 2 4 Crabgrass 9 8 1 6 10 1 6 0 8 2 1 0 0 0 8 - 0 8 0 4 10 3 0 10 9 9 Giant foxtail 9 10 2 6 10 2 3 1 5 2 2 0 0 0 1 0 0 9 0 1 10 2 0 10 10 10 Lambsquarter 4 10 3 0 9 7 10 0 2 0 - 0 0 - 3 0 0 0 0 0 9 0 0 9 9 9 Morningglory 0 4 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 5 0 Nutsedge 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 1 3 0 0 4 0 1 0 0 0 0 0 0 0 0 0 0 0 0 2 4 0 Rice 1 0 0 0 1 1 1 0 0 0 0 0 0 0 1 0 0 0 0 0 2 0 Sorghum 2 6 0 0 2 0 2 0 0 0 0 0 0 0 0 0 0 1 0 0 3 0 Soybean 1 0 0 0 2 0 0 0 0 0 0 - 0 0 0 4 0 2 0 0 1 0 Sugar beet 7 8 2 0 10 1 6 0 4 0 1 0 0 0 2 0 0 2 0 2 9 0 Velvetleaf 0 8 0 0 7 1 3 0 0 0 0 0 0 0 0 0 0 1 0 1 5 0 Wheat 1 2 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 3 Wild buckwheat 5 10 0 0 8 0 10 0 0 - - 0 0 0 0 0 0 1 0 0 3 0 0 3 Wild oat 6 6 0 0 9 0 1 0 2 0 0 0 0 0 3 0 0 4 0 0 7 0 0 10 Velvetleaf 10 2 3 0 2 0 10 10 10 1 10 0 9 10 Wheat 2 1 1 0 1 0 2 4 3 0 3 1 5 3 Wild buckwheat 3 1 1 0 2 0 5 10 6 9 8 4 7 4 Wild oat 3 3 0 2 3 2 2 6 4 4 6 4 9 9 Chickweed 6 0 9 6 0 9 9 9 5 8 0 9 9 8 0 9 4 9 9 9 10 8 Cocklebur 0 0 4 0 0 2 5 3 0 0 0 0 2 0 0 0 0 0 3 4 3 . 0 Corn 0 0 9 7 0 7 7 6 1 2 0 4 7 0 0 4 0 6 7 9 8 1 Cotton 0 0 9 0 0 3 6 5 0 0 0 0 0 0 0 0 0 2 1 10 9 1 Crabgrass 5 0 10 9 1 ,10 10 10 5 2 2 9 9 5 3 6 8 10 10 10 10 10 Giant foxtail 7 0 10 8 2 10 10 10 6 8 2 10 10 5 5 9 8 10 10 10 10 9 Lambsquarter - 0 10 6 0 10 10 9 7 7 0 9 9 5 0 9 6 9 10 10 10 10 Morningglory 0 0 9 2 0 10 10 10 5 3 0 8 10 1 1 10 2 8 10 10 10 10 Nutsedge 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 3 7 5 0 Rape 0 0 10 4 0 10 10 10 0 1 0 8 10 1 0 9 1 9 10 10 10 10 Rice 0 0 4 0 0 5 4 4 0 0 0 0 0 0 0 0 2 1 4 3 7 1 Sorghum 0 0 7 6 1 8 8 7 0 3 - 1 8 0 0 3 2 3 3 6 9 1 Soybean 0 0 4 0 0 5 3 5 0 1 0 1 8 0 0 5 0 6 4 8 9 1 Sugar beet 8 0 10 9 0 10 10 10 1 4 0 10 10 9 0 9 4 10 9 10 10 9 Velvetleaf 0 0 10 1 0 10 10 10 4 2 0 9 10 1 0 5 1 10 10 10 10 5 Wheat 0 0 6 4 0 6 6 5 1 2 0 8 7 0 0 2 0 1 1 10 10 1 Wild buckwheat 10 0 10 3 0 10 9 9 1 3 0 8 7 1 0 1 0 10 10 10 9 8 Wild oat 3 0 10 4 0 10 9 10 4 6 0 9 9 1 0 2 1 4 5 10 10 7 to rt o oι m σι σ c r- '3 , o o o o rt θ '-" σ o θ "!- , ^3' ~ 00 rt rt rt rt rt rt rt rt m w r^ σi σi to σi rt rt rt o σ σi co o oo rt rt w oo o 'j' rt vo rt «a « m σι ιn r~ -n o rt rt θ o o σι σι o o rt rt co σι o co m vo 00 rt rt rt rt rt rt t- o o o o o rt co ιn o o o o oo o w co ^ f o o -n «j' o rt rt rt rt rt rt rt rt rt r. rt rt w o w o v "* I o o p- oo r- o o o o rt o w w o o ro 00 rt rt ^• o oi o oo oi co m oo o o o o o oo rt in in o o po o o. 03 o oi o oi n- o o vo o o o o w o co o w o o vo o o co rt rt rt rt rt rt Ol w o o σ σι σi rt '3< -n o o o o »3' o w ιn co o o rt o co r- rt rt rt tr rt rt rt rt rt rt rt O rt O W O rt O O O f- W W O O O O O O O O O O O o oi oi vo w w o rt o o o co rt o ^ o rt o r- m o ^j' w f- rt rt rt o oo oo ro oi o co o o o u. 's' «3' ^ > o w o oi vo rt w co r » τ-i rt rt τ-i in rt oi m r^ co oi o oo o o o σi r^ o co o ^' ro σi rt o vo co O r- u rt O rt Ol CO W ^C O O O W -n O rt O O O O O ' rt O O O r- co o co oo "3 , w ^t , o o o σ σι σι co o o o o ro o o o to o r- τ-i w o « * vo rt co co o rt o oo oi o o o co o rt o oo o rt ^i< co r. τ-i o σι oo -n co σ rt in r- o oo o ιn o co ιn o -n o o o "* -n r- rt rt rt rt rt O o co σi co w σ o co o o σi σi o r- o rt O rt σ oo o co w r- rt σ o eo oo '0' w σι o o o o o σι co o -n w o o σι co o -n co co rt co τ3 , to σι co vo σ o ^' rt o σι σι ρ- w co w w co o co co r~ ιn co rt rt -i r- o w I rt c^ o o o c^ ^o m o o o o o σl rt o o "3 , vo rt to co σi ci o o o p co m o o o o o o rt w co o r- to o o o rt rt rt rt rt rt rt rt rt rt rt τ-i in co o o o eo σi in to co o o o o co o w w vo o o vo vo σ to rt rt rt rt rt rt rt rt rt rt fl 4J -C CO r-i cfl ^ H CO •H M >n φ 01 U Cfl Cfl φ M A 2 M CO O 4J 4J O a o ω en w co Ό M O M M rt Φ fl X O CD • σ s co o 3 co O cfl O Φ Φ φ O 4-1 a CD C~ M .. C.O- M. M.. φ- Λ— cfl <w en Oi C Λ rt 3 CO rt t-| ι Cβ M θ Oι -* Φ C M σ C O Λ O φ , 4 ,!-. 4J M rt O O14J C0 -H Φ A Φ M φ 4-> Φ H rt C C0 O Cβ O ---. G 4-> Λ C -Q C C0 Φ Φ tJi -Q cfl > .fl "d O £1 4 ω M M O cO Φ -H O M 4 CO Cθ E M 4-l p U M ι en rt Φ rt rt CO C0 (--l cfl c0 Φ rt -C Λ O O O M -H cfl O 3 C0 -H O O 3 Φ -C -H -H H o-; c-. cQ c-ι m ca u u u u u u c. h-i S 2 a- α co co co > -2 S ≥ Rape 10 2 10 9 10 Rice 1 0 0 1 2 Sorghum 2 Soybean 7 0 5 4 9 3 1 Sugar beet 10 8 10 10 10 9 10 Velvetleaf 10 1 2 10 10 1 10 Wheat 9 0 0 0 0 Wild buckwheat 10 0 10 - 10 Wild oat 9 3 10 10 3 10 Velvetleaf 0 0 0 0 0 0 10 8 10 Wheat 0 0 0 0 0 0 0 Wild buckwheat 10 Wild oat 0 2 0 1 Table B COMPOUND Rate 200 g/ha 46 47 49 51 52 53 54 56 57 58 59 60 61 62 63 64 65 66 67 69 70 71 72 73 74 75 76 77 POSTEMERGENCE Barley 0 1 0 0 2 0 2 2 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass 0 0 0 4 2 1 3 5 1 1 7 1 2 2 1 2 1 2 1 0 4 0 1 0 1 1 1 4 Bedstraw 3 2 4 4 5 5 5 7 2 2 4 2 2 2 2 2 2 3 3 0 7 2 4 1 5 7 5 7 Blackgrass 0 2 2 1 3 0 1 3 1 0 2 0 1 0 0 1 0 2 0 0 1 0 0 1 2 1 1 1 Cheatgrass 0 1 0 1 2 1 2 3 0 0 1 0 0 0 0 1 1 1 1 0 2 0 1 0 2 0 1 2 Chickweed 2 2 2 4 4 3 4 6 0 2 3 1 4 2 1 3 1 3 1 0 2 1 3 0 4 2 2 3 Cocklebur 0 0 3 1 2 2 1 6 2 0 5 0 3 0 1 1 0 1 0 0 3 0 2 0 1 1 1 1 . Corn 0 2 0 1 2 0 2 2 0 1 2 1 3 1 1 1 0 1 0 0 1 0 1 0 1 1 0 1 Cotton 2 7 7 9 10 5 8 9 5 6 5 4 9 2 1 1 0 1 0 0 3 0 1 0 2 0 1 1 Crabgrass 0 0 0 3 6 2 8 7 1 2 4 4 3 2 1 3 1 2 1 0 2 1 2 3 1 0 1 2 Giant foxtail 0 1 0 2 2 1 3 3 2 2 6 2 2 2 1 2 1 2 1 0 2 0 1 0 2 0 1 2 Lambsquarter 2 2 - 3 7 3 5 8 3 0 9 - 3 1 1 2 0 1 1 - - 1 - 0 3 2 7 2 Morningglory 3 4 6 1 2 1 0 7 0 2 8 3 1 1 0 1 1 1 1 0 3 1 2 0 4 5 - 2 Nutsedge 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 Rape 1 0 2 3 2 5 5 8 6 0 4 0 4 1 1 2 0 2 0 0 5 0 5 0 1 5 1 1 Rice 0 0 0 1 1 0 1 2 1 0 2 1 2 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 Sorghum Soybean Sugar beet Velvetleaf Wheat Wild buckwheat 2 3 2 3 4 5 7 8 1 2 1 1 0 1 1 1 1 2 0 0 1 1 1 1 3 2 2 Wild oat 0 1 0 0 0 0 1 3 0 0 1 0 0 0 0 0 1 0 0 0 2 1 0 0 1 1 0 Giant foxtail 8 8 5 8 3 3 2 3 2 6 8 8 1 7 2 5 4 2 7 2 3 Lambsquarter 7 4 7 6 2 5 2 8 1 6 3 6 2 8 4 5 5 5 5 7 6 Morningglory 8 5 7 6 4 3 - 6 3 5 3 6 2 8 2 7 4 4 2 3 5 Nutsedge 3 2 0 4 1 0 0 2 0 1 2 1 - 2 0 2 1 2 1 4 0 Rape 9 9 3 4 4 4 0 5 2 3 9 9 4 5 3 5 5 7 2 6 7 Rice 4 3 4 6 2 0 2 3 0 2 1 2 0 6 1 3 2 3 1 2 2 Sorghum 4 2 2 3 0 0 2 2 0 0 2 1 1 2 0 4 3 3 3 0 3 Soybean 5 1 5 4 2 3 3 5 3 6 5 7 6 8 6 5 5 6 2 7 3 Sugar beet 9 8 10 8 5 8 3 8 6 9 9 8 7 8 7 9 10 8 8 7 8 Velvetleaf 5 2 4 3 3 2 4 3 6 8 1 2 3 3 1 4 5 2 1 3 2 Wheat 6 6 1 2 1 0 0 1 1 1 2 3 0 1 1 1 2 1 1 1 1 Wild buckwheat 6 6 5 7 2 1 2 5 1 1 7 7 1 5 4 5 6 4 3 2 3 Wild oat 7 4 2 3 1 0 1 1 1 1 1 8 1 2 1 3 5 2 4 1 2 Velvetleaf Wheat Wild buckwheat Wild oat Chickweed 9 10 4 7 9 5 3 4 - 3 - 3 3 3 4 3 0 6 4 Cocklebur 6 8 6 3 3 1 1 3 4 4 1 1 0 2 2 2 1 3 2 Corn 8 7 1 6 3 1 1 2 2 4 1 1 1 1 3 2 1 5 4 Cotton 9 9 8 7 8 8 6 8 8 8 5 2 4 7 9 9 4 9 10 Crabgrass 8 7 3 2 3 1 0 3 2 3 1 1 1 6 8 2 2 6 6 Giant foxtail 8 6 2 2 2 1 0 3 2 2 1 1 1 4 1 1 0 6 6 Lambsquarter 9 9 7 9 8 3 5 4 6 3 2 6 5 7 7 8 5 9 2 Morningglory 8 9 5 4 6 2 3 5 5 4 2 3 3 5 2 6 2 7 6 Nutsedge 3 2 0 0 0 0 0 1 2 1 0 0 0 1 1 0 0 2 2 Rape 4 9 7 9 9 4 2 7 0 1 2 2 3 2 3 3 0 6 1 Rice 5 2 0 1 0 0 0 2 2 2 0 0 0 0 1 0 0 2 0 Sorghum 6 6 1 2 2 0 0 2 1 1 1 0 0 1 1 1 1 3 1 Soybean 8 8 6 8 6 3 4 7 7 6 3 5 4 6 6 5 1 6 6 5 1 8 Sugar beet 8 10 9 9 9 6 5 9 7 8 2 2 3 5 3 6 0 10 1 9 0 - Velvetleaf 6 3 6 2 2 1 1 1 3 2 1 1 1 2 2 2 3 6 3 8 2 6 Wheat 2 6 2 3 2 0 0 1 0 0 0 0 0 0 0 0 0 2 1 1 0 2 Wild buckwheat 8 9 5 6 7 2 5 6 3 2 3 2 2 5 0 2 0 5 2 9 3 5 Wild oat 5 8 2 3 2 0 0 1 0 1 1 0 0 0 0 0 0 5 2 4 0 7 Table B COMPOUND Rate 200 g/ha 1 3 4 5 6 7 9 10 11 12 14 17 18 19 21 22 23 24 26 28 29 30 31 32 33 39 40 41 45 PREEMERGENCE Barley 0 0 0 2 0 0 0 0 0 0 0 0 1 0 10 0 0 0 3 0 0 3 0 1 0 0 0 0 5 Barnyardgrass 5 0 0 9 0 7 0 0 0 1 8 5 10 5 10 3 1 0 10 0 0 10 2 9 2 8 0 0 10 Bedstraw 3 0 1 10 0 5 0 0 - 1 0 1 10 0 10 - - 0 10 5 0 7 0 4 1 2 0 0 7 Blackgrass 3 0 1 8 0 2 0 0 0 1 5 10 10 4 10 0 1 0 10 0 0 10 0 7 2 7 0 0 8 Cheatgrass 1 0 0 5 0 2 0 0 0 0 0 2 6 2 6 0 1 0 8 0 0 9 0 4 0 2 0 0 5 Chickweed 0 0 0 6 0 0 0 0 0 3 5 0 9 8 9 7 4 0 9 0 0 9 0 8 1 8 0 0 10 Cocklebur 0 0 0 1 0 - 0 0 0 0 1 0 1 0 1 0 0 0 0 0 0 1 0 0 0 0 0 0 0 Corn 0 0 0 2 0 0 0 0 0 0 3 0 4 0 4 2 0 0 3 0 0 3 0 3 0 0 0 0 2 Cotton 0 0 1 1 0 0 0 0 0 0 0 0 2 0 1 0 0 0 0 0 0 3 0 0 0 0 0 0 0 Crabgrass 10 0 8 10 0 8 0 0 6 8 9 8 10 10 10 9 7 0 10 5 4 10 6 10 4 8 0 0 10 Giant foxtail 10 0 7 10 0 9 0 0 3 2 9 9 10 9 10 4 10 0 10 3 4 10 7 10 7 10 0 0 10 Lambsquarter 6 0 - 10 0 8 0 0 0 10 10 - 10 - 10 - - 0 - 0 0 - - - 0 9 0 0 9 Morningglory 0 0 0 7 0 2 0 0 0 0 2 1 8 3 10 1 0 0 3 0 0 7 0 2 1 1 0 0 2 Nutsedge 0 0 0 0 0 - 0 0 0 10 2 0 0 0 1 0 0 0 0 - - 2 0 0 0 0 0 0 0 Rape 5 0 0 5 0 7 0 0 0 2 4 1 2 1 7 0 0 0 8 0 0 3 0 2 1 2 0 0 8 Rice 0 0 0 2 0 0 0 0 0 0 4 0 3 0 3 0 0 0 0 0 0 1 0 1 0 1 0 0 0 Sorghum 0 0 0 1 0 0 0 0 0 0 3 0 3 1 2 0 0 0 1 0 0 0 0 0 0 0 0 0 1 Soybean 0 0 0 2 0 0 0 0 0 1 3 0 3 0 9 1 0 0 1 0 0 4 0 0 0 0 0 0 1 Sugar beet 9 0 6 10 0 8 0 0 0 10 8 0 4 7 2 0 0 0 10 0 0 9 0 9 2 9 0 0 10 Velvetleaf 4 0 2 5 0 0 0 0 0 0 5 1 6 0 8 4 6 0 7 0 0 2 0 4 0 1 0 0 3 Wheat 0 0 0 2 0 0 0 0 0 0 0 1 1 0 1 0 0 0 3 0 0 2 0 1 0 0 0 0 2 Wild buckwheat 0 0 6 - 0 5 0 - - 2 2 0 1 0 10 1 0 0 7 0 0 5 0 - 0 6 0 0 2 Wild oat 1 0 0 8 0 0 0 0 0 0 0 2 9 4 10 0 1 0 9 0 0 8 0 4 1 6 0 0 9 Table B COMPOUND Rate 200 g/ha 78 79 81 82 83 85 86 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 PREEMERGENCE Barley 0 0 0 0 1 0 0 2 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass 0 6 3 1 2 0 0 5 0 0 0 0 0 0 0 0 0 0 0 Bedstraw 0 1 2 0 7 - 0 4 0 0 0 0 0 - 0 0 - 0 0 Blackgrass 0 6 7 0 3 0 0 7 0 0 0 0 0 0 0 0 0 0 0 Cheatgrass 0 2 5 0 1 0 0 7 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 4 0 0 Chickweed 0 1 5 0 7 0 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 Cocklebur 0 - 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 10 8 2 7 0 1 -10 0 1 0 0 1 0 0 0 0 4 0 0 6 0 0 9 0 0 Giant foxtail 0 10 5 2 7 0 2 10 0 0 0 1 1 0 0 0 0 0 0 0 2 0 0 9 0 0 Lambsquarter 0 6 1 0 9 0 0 8 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 5 0 0 Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 1 0 0 0 0 0 1 0 0 0 0 0 - 0 0 0 0 0 0 0 0 1 1 0 0 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sorghum 0 2 0 0 3 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sugar beet 0 5 8 1 0 0 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 0 Velvetleaf 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 Wheat 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild buckwheat 0 1 5 0 1 0 0 3 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 1 0 0 Wild oat 0 2 3 0 2 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 4 0 0 Lambsquarter 9 9 9 7 3 3 0 2 2 9 10 10 8 Morningglory 10 7 2 9 2 0 0 0 0 5 10 10 1 Nutsedge 3 2 1 6 0 0 - 0 0 0 2 3 0 Rape 7 8 3 1 2 2 0 2 0 2 10 10 2 Rice 5 4 2 2 1 0 0 0 0 0 2 5 0 Sorghum 4 2 3 5 0 0 0 0 0 0 3 4 2 Soybean 5 4 3 3 0 0 0 0 0 3 2 4 2 Sugar beet 10 10 8 9 6 3 0 2 0 9 10 10 10 Velvetleaf 7 4 2 5 1 0 0 0 0 10 4 10 0 Wheat 2 0 1 0 0 0 0 0 0 0 2 1 0 Wild buckwheat 2 7 1 1 0 0 0 0 0 0 6 5 2 Wild oat 4 2 2 0 2 0 0 1 0 1 4 4 1 Velvetleaf 0 0 0 0 0 5 0 0 10 10 5 0 0 0 1 5 0 0 0 0 2 6 Wheat 0 0 0 0 0 4 0 0 4 4 2 0 0 0 2 - 0 0 0 0 0 0 Wild buckwheat 0 0 0 9 - 10 3 0 10 8 8 0 0 0 2 5 0 0 0 0 10 10 Wild oat 8 0 0 0 0 8 0 0 8 8 9 2 2 0 1 3 0 0 1 0 -. ? Chickweed 9 10 4 9 8 0 8 2 3 7 6 1 2 8 1 - 0 9 7 9 - 9 Cocklebur 1 1 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 . 0 Corn 5 6 0 4 1 0 0 0 0 0 0 0 0 0 0 0 0 2 3 1 0 0 Cotton 0 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 2 0 0 Crabgrass 10 10 9 10 9 0 4 3 4 9 1 1 0 7 9 3 1 10 10 10 0 9 Giant foxtail 10 10 7 8 6 2 4 5 5 6 2 0 0 3 9 3 0 9 9 10 0 9 Lambsquarter 9 9 8 9 9 0 9 9 9 9 4 8 10 6 2 1 0 9 5 10 0 10 Morningglory 10 10 5 10 6 1 2 3 2 2 0 0 0 1 1 0 1 10 0 10 0 9 Nutsedge 6 0 0 1 0 0 0 0 0 0 0 0 0 10 0 0 0 - 0 0 0 0 Rape 8 10 5 10 10 0 0 2 0 0 2 0 0 2 2 0 0 4 1 9 0 10 Rice 2 4 0 0 0 0 0 0 1 1 0 0 0 0 0 0 0 1 0 1 0 1 Sorghum 2 7 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 2 Soybean 3 7 0 3 0 0 0 0 0 1 0 0 0 0 0 0 0 2 0 0 0 3 Sugar beet 10 10 7 10 9 3 5 5 4 10 1 8 0 9 2 2 0 9 3 9 0 5 Velvetleaf 9 7 1 6 1 0 0 2 1 1 0 0 0 0 2 0 1 7 5 10 1 10 Wheat 4 3 0 1 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 Wild buckwheat 10 9 0 4 4 0 - 2 1 2 0 2 0 1 0 1 0 10 0 10 0 - Wild oat 10 7 0 3 4 0 2 1 1 0 0 0 0 2 2 0 0 5 3 8 0 8 TABLE B COMPOUND Rate 2000 g/ha 240 241 242 243 245 POSTEMERGENCE TEST C 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 (paddy 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 paddy test. Water depth was approximately 2.5 cm for the paddy test and was maintained at this level for the duration of the test. Plant spec.es in the preemergence and postemergence tests consisted of barley (Hordeu vulgare) , bedstraw ( Galium aparine) , blackgrass (Alopecurus myosuroides) , chickweed (Stellaria media) , corn ( Zea mays) , cotton ( Gossypium hirsutum) , crabgrass (Digitaria sanguinalis) , downy brome (Bromus tectorum) , duck salad (Heteranthera limosa) , giant foxtail (Setaria faberii) , lambs.quarters (Chenopodium album) , morningglory (Ipomoea hederacea) , pigweed ( lmaranthusretroflexus) , rape (Brassica napus) , ryegrass (Lolium multiflorum) , sorghum (Sorghum bicolor) , soybean ( Glycine max) , speedwell ( Veronica persica) , sugar beet (Beta vulcjari-s) , 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 postemergence portion of the test. Plant species in the paddy test consisted of barnyardgrass (Echinochloa crus-galli ) , rice ( Oryza sativa) , and umbrella sedge ( Cyperus difformis) . 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 C, were recorded on a 0 to 10 scale where 0 is no injury and 10 is complete control. A dash (-) response means no test result. Table C COMPOUND Rate 500 g/ha 23 39 42 56 74 77 79 88 109 111 113 114 124 134 155 160 161 POSTEMERGENCE Barley Igri _ _ _ _ _ _ _ _ _ _ _ _ _ _ 50 20 20 Barnyard 2 leaf - - - - - - - - - - - - - - 95 - - Barnyardgrass 100 90 75 85 65 70 85 100 100 95 95 90 100 95 - 100 100 Bedstraw - - - - - - - - - - - - - - 90 70 70 Blackgrass - - - - - - - - - - - - - - 85 80 80 Chickweed - - - - - - - - - - - - - - 90 70 60 Corn - - - - - - - - - - - - - - 40 30 50 Cotton ' 40 50 40 Crabgrass - - - - - - - - - - - - - - 70 80 50 Downy Brome - - - - - - - - - - - - - - 40 40 30 Duck salad 40 90 90 70 85 90 70 30 90 95 90 85 95 85 70 70 65 Giant foxtail - - - - - - - - - - - - - - 95 85 70 Lambsquarters - - - - - - - - - - - - - - 95 90 70 Morningglory - - - - - - - - - - - - - - 90 50 80 Pigweed - - 90 70 70 Rape - - - - - - - - - - - - - - 90 60 40 Rice Japonica 65 85 70 45 40 75 50 40 55 45 75 0 90 70 75 55 55 Ryegrass - - - - - - - - - - - - - - 70 40 50 Sorghum - - - - - - - - - - - - - - 20 30 20 Soybean - - - - - - - - - - - - - - 50 60 50 Speedwell _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ Sugar beet _ _ _ _ _ _ _ _ _ _ _ _ _ _ 1( )0 90 90 Umbrella sedge 80 90 90 70 80 90 80 60 90 90 90 90 90 85 95 90 90 Velvetleaf _ _ _ _ _ _ _ _ _ _ _ - - - 50 50 50 Wheat - - - - - - - - - - - - - - 20 10 20 Wild buckwheat - - - - - - - - - - - - - - 60 70 70 Wild oat - - - - - - - - - _ _ _ - - 60 50 50 *~ *> tV > »' Table C COMPOUND Rate 250 g/ha 14 18 21 23 26 30 32 39 42 45 55 56 59 74 77 79 88 109 111 113 114 124 POSTEMERGENCE Barley Igri - - - - - - - 30 - - - - - - - - - - - - - - Barnyard 2 leaf - - - - - - - - - - - - - - - _ _ _ _ _ _ _ Barnyardgrass 95 100 100 100 100 100 95 100 70 85 90 75 85 65 65 80 100 100 95 95 70 100 Bedstraw - - - - - - - 60 - - - - - - - - - - - - - - Blackgrass - - - - - - - 50 - - - - - - - - - - - - - - Chickweed - - - - - - - 70 - - - - - - - - - - - - - - Corn - - - - - - - 30 - - - - - - - - - - - - - - Cotton - - - - - - - 70 - - - - - - - - - - - - - - Crabgrass - - - - - - - - 70 _ _ _ _ _ _ _ _ _ _ _ _ _ _ Downy Brome - - - - - - - 30 - - - - - _ - - _ _ - - - _ Duck salad 30 85 90 30 85 90 90 80 90 90 85 65 70 80 80 20 10 90 90 90 80 90 Giant foxtail - - - - - - - 90 - - - - - - - - - - - - - - Lambsquarters - - - - - - - 90 - - - - - - - - - - - - - - Morningglory - - - - - - - 20 - - - - - - - - - - - - - - Pigweed - - - - - - - 80 - - - - - - - - - - - - - - Rape - - - - - - - 70 - - - - - - - - - - - - - - Rice Japonica 75 90 90 55 85 90 70 75 65 70 80 40 65 35 70 40 35 50 35 45 0 80 Ryegrass - - - - - - - 10 - - - - - - - - - - - - - - Sorghum - - - - - - - 40 - - - - - - - - - - - - - - Soybean - - - - - - - 70 - - - - - - - - - - - - - - Speedwell - - - - - - - 90 - - - - - - - - - - - - - - Sugar beet - - - - - - - 80 - - - - - - - - - - - - - - Umbrella sedge 95 90 90 75 90 90 90 90 90 90 90 65 85 55 85 60 30 90 80 90 80 90 Velvetleaf - - - - - - - 70 - - - - - - - - - - - - - - Wheat - - - - - - - 10 - - - - - - - - - - - - - - Wild buckwheat - - - - - - - 60 - - - - - - - - - - - - - - Wild oat - - - - - - - 40 - - - - - - - - - - - - - - Table C COMPOUND Rate 250 g/ha 125 127 132 134 142 144 149 150 155 160 161 162 163 POSTEMERGENCE Barley Igri - - - - - 0 - • Barnyard 2 leaf - 90 - - 85 85 Barnyardgrass 100 100 95 90 95 100 100 95 Bedstraw - 90 Blackgrass - 70 Chickweed - 90 Corn - 60 Cotton - 90 Crabgrass - 90 Downy Brome - 60 Duck salad 95 90 90 80 0 80 95 75 90 90 Giant foxtail - 90 Lambsquarters - 90 Morningglory - 90 Pigweed - 90 Rape - 100 Rice Japonica 90 85 65 65 50 85 75 70 55 65 Ryegrass - 60 Sorghum - 70 Soybean - 80 Speedwell - 100 Sugar beet - 100 Umbrella sedge 90 95 90 75 45 90 90 80 90 90 Velvetleaf - 90 Wheat - 20 Wild buckwheat - 40 Wild oat - 60 Table C COMPOUND Rate 125 g/ha 5 14 18 21 23 26 30 32 39 42 45 56 59 74 76 77 79 88 109 111 113 POSTEMERGENCE Barley Igri χo - - - - - - - 20 - - - - - - - - - - - - Barnyard 2 leaf - - _ - - - - _ _ - - - _ - _ _ _ _ _ _ _ Barnyardgrass 100 90 100 100 85 100 100 95 100 65 85 70 80 45 25 60 65 100 100 90 90 Bedstraw 100 - - - - - - - 40 - - - - - - - - - - - - Blackgrass 60 - - - - - - - 30 - - - - - - - - - - - - Chickweed 55 _ _ _ _ _ _ _ 50 - - - - - - - - - - - - Corn _ _ _ _ _ _ _ _ 20 - - - - - - - - - - - - Cotton 60 - - - - - - - 50 - - - - - - - - - - - - Crabgrass 60 - - - - - - - 50 - - - - - - - - - - - - Downy Brome Q - - - - - - - - 20 - - - - - - - - - - - - Duck salad 95 0 85 90 0 80 65 85 75 90 80 40 30 65 75 70 10 0 90 50 80 Giant foxtail 60 - - - - - - - 70 - - - - - - - - - - - - Lambsquarters 50 - - - - - - - 90 - _ _ _ _ _ _ _ _ _ Morningglory 60 - - - - - - - 10 - - . _ - _ _ _ _ _ _ _ Pigweed 50 - - - - - - - 80 - - - - - - - - - - - - Rape 10 - - - - - - - 70 - - - - - - - - - - - - Rice Japonica 85 55 80 85 55 70 80 65 60 55 65 30 50 20 30 70 35 25 20 10 35 Ryegrass 20 - - - - - - - 0 - - - - - - - - - - - - Sorghum 60 _ _ _ _ _ _ _ 30 _ _ _ _ _ _ _ _ _ _ _ _ Soybean 60 - - - - - - - 60 - - - - - - - - - - - - Speedwell 100 - - - - - - - 90 - - - - - - - - - - - - Sugar beet 100 - - - - - - - 80 - - - - - - - - - - - - Umbrella sedge 95 90 90 90 65 90 90 90 90 90 90 45 85 40 80 70 30 20 90 80 80 Velvetleaf 60 - - - - - - - 60 - - - - - - - - - - - - Wheat 10 - - - - - - - 10 - - - - - - - - - - - - Wild buckwheat 40 - - - - - - - 30 - - - - - - - - - - - - Wild oat 10 - - - - - - - 30 - - - - - - - - - - - - Table C COMPOUND Rate 125 g/ha 114 124 125 127 132 134 142 144 149 150 155 160 161 162 163 POSTEMERGENCE Barley Igri - - - - - - - - - - Barnyard 2 leaf - - - - - - - - 60 80 Barnyardgrass 60 90 100 100 95 85 95 95 Bedstraw _ _ _ - - , Blackgrass - _ _ _ - , Chickweed - Corn - Cotton - _ _ _ _ Crabgrass - Downy Brome - Duck salad 70 80 90 80 85 65 90 60 70 90 Giant foxtail _ _ _ _ _ Lambsquarters _ _ _ _ _ Morningglory - Pigweed - - Rape - Rice Japonica 0 65 80 75 65 45 65 65 50 60 Ryegrass - - - - - - - - - - Sorghum - Soybean _ _ _ _ _ Speedwell - Sugar beet _ _ _ _ _ Umbrella sedge 70 80 90 90 80 35 85 65 80 85 Velvetleaf - Wheat - _ _ _ _ Wild buckwheat - - _ _ - Wild oat _ _ _ _ _ _ _ 3o Table C COMPOUND Rate 125 g/ha 5 14 18 21 26 30 32 39 42 45 56 59 74 76 77 79 88 109 111 113 114 PREEMERGENCE Barley Igri 0 30 40 100 40 40 0 10 0 10 0 0 0 0 0 0 0 50 10 20 0 Bedstraw 100 40 80 100 80 80 70 40 80 50 60 100 30 50 80 20 40 100 80 90 0 Blackgrass 90 50 98 100 100 100 100 100 40 90 70 70 50 20 0 50 20 80 90 70 20 Chickweed 100 50 90 80 100 90 100 90 50 70 50 20 80 40 0 20 50 100 90 50 50 Corn 60 50 50 70 40 50 20 30 40 10 0 40 50 0 0 10 0 50 50 50 0 Cotton 0 30 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 100 100 100 100 100 100 100 100 98 100 100 100 100 100 60 100 90 100 100 100 100 Downy Bro e 35 20 80 30 60 30 20 20 0 20 0 0 0 0 0 0 0 50 20 30 0 Giant foxtail 100 70 100 100 100 100 100 100 90 100 100 100 90 80 60 90 100 100 100 100 90 Lambsquarters 100 100 100 100 100 100 100 100 100 100 70 100 100 80 50 100 50 100 90 100 50 Morningglory 30 c 80 80 80 60 20 50 60 10 20 40 0 0 20 10 0 100 80 100 20 Pigweed 100 70 70 100 100 80 90 90 50 100 100 70 90 80 70 60 20 100 90 80 80 Rape 60 60 50 100 70 20 50 20 0 20 20 0 50 0 0 10 0 100 95 10 20 Ryegrass 60 20 70 60 60 40 60 20 0 20 0 0 40 0 0 0 0 60 50 40 20 Sorghum 90 20 50 90 40 25 60 20 30 20 20 30 10 0 20 10 30 60 50 30 20 Soybean 40 0 40 50 40 30 0 0 20 0 0 0 0 0 0 0 0 30 0 10 0 Speedwell 100 - - 100 100 - 50 80 100 100 100 100 10 0 80 100 100 100 - 100 80 Sugar beet 100 90 100 100 100 100 100 95 50 70 50 60 50 30 50 50 50 100 100 100 30 Velve. eaf 100 60 100 100 80 80 80 50 0 25 20 80 70 0 20 50 20 100 90 100 30 Wheat 0 30 30 70 40 30 0 0 0 0 0 0 0 0 0 0 0 40 10 20 0 Wild buckwheat 20 30 20 80 80 70 80 50 20 0 20 0 0 0 30 0 0 30 100 40 0 Wild oat 30 20 60 100 60 60 25 20 0 20 20 0 0 0 0 0 0 50 10 40 0 Table C COMPOUND Rate 62 g/ha 5 14 18 21 23 26 30 32 39 42 45 56 59 74 76 77 79 88 109 111 113 POSTEMERGENCE Barley Igri - - - - - - - - χo - - - - - - - - - - - - Barnyard 2 leaf - - - - - - - - - - - _ _ _ _ _ _ _ _ _ _ Barnyardgrass 100 80 100 100 75 100 100 90 85 50 80 50 75 25 25 55 45 70 90 65 75 Bedstraw - - - - - - - - 30 - - - - - - - - - - - - Blackgrass - - - - - - - - 20 - - - - - - - - - - - - Chickweed - - - - - - - - 30 - - - - - - - - - - - - Corn - - - - - - - - 10 - - - - - - - - _ _ _ _ Cotton - - - - - - - - 30 - - - - - - - - - - - - Crabgrass - - - - - - - - 20 - - - - - - - - - - - - Downy Brome - - - - - - - - 10 - - - - - - - - - - - - Duck salad 90 0 75 80 0 80 55 0 50 40 60 10 10 0 40 40 0 0 80 10 70 Giant foxtail - - - - - - - - 30 - - - - - - - - - - - - Lambsquarters - - - - - - - - 85 - - - - - - - - - - - - Morningglory - - - - - - - - 10 - - - - - - - - - - - - Pigweed - - - - - - - - 60 - - - - - - - - - - - - Rape - - - - - - - - 60 - - - - - - - - - - - - Rice Japonica 80 35 75 75 40 65 75 45 40 35 50 25 40 0 0 65 10 10 0 0 30 Ryegrass - - - - - - - - 0 - - - - - - - - - - - - Sorghum - - - - - - - - 20 - - - - - - - - - - - - Soybean - - - - - - - - 50 - - - - - - - - - - - - Speedwell - - - - - - - - 85 - - - - - - - - - - - - Sugar beet - - - - - - - - 80 - - - - - - - - - - - - Umbrella sedge 90 70 90 85 50 85 90 85 90 80 85 10 75 20 80 0 10 0 80 60 75 Velvetleaf - - - - - - - - 30 - - - - - - - - - - - - Wheat - - - - - - - - 10 - - - - - - - - - - - - Wild buckwheat - - - - - - - - 10 - - - - - - - - - - - _ Wild oat - - - - - - - - 20 - - - - - - - - - - - - Table C COMPOUND Rate 62 g/ha 114 124 125 127 132 134 142 144 149 150 155 160 161 162 163 POSTEMERGENCE Barley Igri _ _ _ _ _ _ Barnyard 2 leaf - - - - - - - - 55 65 . Barnyardgrass 40 85 95 70 75 75 95 95 Bedstraw _ _ _ _ _ _ Blackgrass _ _ _ _ „ . Chickweed - _ - _ - , Corn _ - _ _ _ , Cotton - _ _ _ - Crabgrass - Downy Brome - Duck salad 65 70 80 75 70 10 85 0 65 70 Giant foxtail - Lambsquarters _ _ _ _ _ Morningglory - Pigweed - Rape - Rice Japonica 0 0 50 35 65 35 60 55 30 50 Ryegrass - - - - - - - - - - Sorghum _ _ _ _ _ Soybean _ _ _ _ _ Speedwell - _ _ _ _ Sugar beet _ _ _ _ _ _ Umbrella sedge 50 70 80 80 20 15 25 80 85 Velvetleaf _ _ _ _ _ _ Wheat _ _ _ _ _ _ Wild,buckwheat _ _ _ _ _ _ Wild oat _ _ _ _ _ _ Ά COMPOUND 14 18 21 26 30 32 39 45 59 76 125 127 132 142 144 149 150 162 163 - - - - - - 10 - - - - - - - 10 - - - - - - - - - - - - - - - - - - 75 - - 35 35 50 100 100 100 100 90 60 70 40 20 80 45 65 75 95 85 95 - - - - - - 20 - - - - - - - 70 - - - - - - - - - - 10 - - - - - - - 20 - - - - - - - - - - 30 - - - - - - - 70 - - - - - - - - - - 10 - - - - - - - 20 - - - - - - - - - - 10 - - - - - - - 60 - - - - - - - - - - 10 - - - - - - - 50 - - - - - - - - - - 10 - - - - - - - 10 - - - - 0 50 80 70 40 0 0 40 0 10 70 70 10 0 0 65 0 0 60 - - - - - - 10 - - - - - - - 40 - - - - - - - - - - 70 - - - - - - - 90 - - - - - - - - - - 10 - - - - - - - 60 - - - - - - - - - - 50 - - - - - - - 80 - - - - - - - - - - 50 - - - - - - - 80 - - - - 25 70 70 25 50 30 0 10 10 0 20 0 40 35 55 55 45 0 35 - 0 - - - - - - - 0 - - - - - - - - - - 10 - - - - - - - 10 - - - - - - - - - - 30 - - - - - - - 60 - - - - - - - - - - 60 - - - - - - - 90 - - - - - - 70 - - - - - - - 100 - - - - 45 90 80 25 80 80 0 75 10 20 80 80 10 0 80 15 30 60 85 - - - - - - 10 - - - - - - - 55 - _ _ _ - - - - - - 0 - - - - - - - 10 - - - - - - - - - - - - - - - - - - 20 - - - - - - - - - - 10 - - - - - - - 10 - - - - Table C COMPOUND Rate 31 g/ha 5 14 18 21 26 30 32 39 45 59 76 125 127 132 142 144 149 150 162 163 PREEMERGENCE Barley Igri 0 0 0 100 0 0 0 0 0 0 0 30 0 0 0 0 0 0 0 0 Bedstraw 0 0 80 80 40 20 0 0 0 0 0 100 70 30 50 90 60 10 70 50 Blackgrass 70 0 50 80 60 60 60 10 40 0 0 60 20 80 60 30 75 10 50 50 Chickweed 80 20 50 60 80 70 80 0 50 0 0 80 30 80 10 80 50 10 50 60 Corn 50 0 20 50 0 0 0 0 0 0 0 20 20 10 0 20 20 0 20 20 Cotton 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 - 0 0 Crabgrass 100 70 100 100 100 100 100 80 100 95 30 80 60 100 100 100 100 85 95 100 Downy Brome 0 0 20 20 50 20 0 0 0 0 0 30 0 10 0 10 0 0 10 20 Giant foxtail 100 30 100 100 100 100 98 70 100 60 0 0 60 100 100 100 100 70 95 100 Lambsquarters 100 90 100 100 100 80 100 60 80 50 0 100 80 90 70 95 90 40 20 70 Morningglory 20 50 40 50 30 30 10 0 0 0 0 50 20 10 0 50 20 0 20 20 Pigweed 100 70 70 50 98 80 80 70 50 50 0 100 60 50 95 90 85 85 90 100 Rape 30 0 0 70 0 0 20 0 0 0 0 60 0 10 0 10 0 0 0 70 Ryegrass 20 0 20 40 30 0 20 0 0 0 0 40 0 20 0 20 10 0 30 50 Sorghum 70 0 0 50 30 0 10 0 0 0 0 0 0 0 0 10 10 0 20 40 Soybean 40 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Speedwell 100 - - 100 90 - 30 - 80 0 0 100 100 95 - - - - - - Sugar beet 90 50 80 100 90 70 90 20 30 0 0 100 100 70 40 80 70 10 70 100 Velvetleaf 60 50 70 80 30 0 50 - 0 30 0 100 50 50 30 90 90 - 0 50 Wheat 0 0 0 50 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild buckwheat 20 0 0 70 30 20 30 0 0 0 0 20 50 10 0 0 20 0 30 10 Wild oat 0 0 30 40 30 0 0 0 0 0 0 40 0 20 10 10 20 10 10 30 Table C COMPOUND Rate 16 g/ha 5 18 21 26 30 76 POSTEMERGENCE Barley Igri 0 - Barnyard 2 leaf - - - - - - Barnyardgrass 100 65 65 50 45 15 Bedstraw 0 Blackgrass _ _ _ _ _ _ Chickweed 30 Corn 20 Cotton 0 - - - - - Crabgrass 0 Downy Brome 0 Duck salad 10 - 30 - - 0 Giant foxtail 0 Lambsquarters 0 Morningglory 0 Pigweed 0 Rape 0 Rice Japonica 55 65 55 20 35 0 Ryegrass 0 Sorghum 0 - - - - - Soybean 10 Speedwell 0 Sugar beet 0 Umbrella sedge 80 - 15 - - 0 Velvetleaf 30 Wheat 0 Wild buckwheat 0 Wild oat o - - - - - Table C COMPOUND Rate 8 g/ha 18 21 26 30 POSTEMERGENCE Barley Igri _ _ _ _ Barnyard 2 leaf - Barnyardgrass 50 40 30 40 Bedstraw - Blackgrass - Chickweed - Corn - Cotton - Crabgrass - Downy Brome - Duck salad - Giant foxtail _ _ _ Lambsquarters - Morningglory - Pigweed - Rape _ _ _ _ Rice Japonica 50 35 10 25 Ryegrass - Sorghum - Soybean _ _ _ _ Speedwell - Sugar beet - Umbrella sedge - Velvetleaf - Wheat - Wild buckwheat - Wild oat - Table C . COMPOUND Rate 4 g/ha 18 21 26 30 POSTEMERGENCE Barley Igri _ _ _ _ Barnyard 2 leaf - Barnyardgrass 30 25 25 25 Bedstraw - - - - Blackgrass _ _ _ _ Chickweed - Corn - Cotton - - Crabgrass - - - - Downy Brome - - - - Duck salad - Giant foxtail - Lambsquarters - Morningglory - Pigweed - Rape - Rice Japonica 20 20 0 0 Ryegrass - Sorghum _ _ _ _ Soybean - - - - Speedwell - Sugar beet - - - - Umbrella sedge - Velvetleaf - - - - Wheat - Wild buckwheat - Wild oat - TEST D Seeds of barnyardgrass (Echinochloa crus-galli ) , cassia ( Cassia obtusifolia) , cocklebur (Xanthium pensylvanicum) , common ragweed (Ambrosia elatior) , corn ( Zea mays) , cotton ( Gossypium hirsutam) , crabgrass (Digitaria spp.), fall panicum (Pani cum dicholomiflorum) , giant foxtail (Setaria faberii ) , green foxtail (Setaria vividis) , ji son weed (Datura stramoni um) , Johnson grass (Sorghum halepense) , morningglory ( Ipomoea spp.), prickly sida (Sida spinose) , signalgrass (Brachiaria platyphylla) , soybean ( Glycine r~ ax) , velvetleaf (Abutilon theophrasti) and wild proso (Panci um miliaceum) were planted into a silt loam soil. Test chemicals, dissolved in a non-phytotoxic solvent, were then applied to the soil surface within one day after the seeds were planted. Pots receiving these preemergence treatments were placed in the greenhouse and maintained according to routine greenhouse procedures. Treated plants and untreated controls were • maintained in the greenhouse approximately 21 days after application of the test compound. Visual evaluations of plant injury responses were then recorded. Plant response ratings, summarized in Table D, are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test. Table D COMPOUND Rate 500 g/ha 32 39 45 56 59 88 109 125 132 PREEMERGENCE Barnyardgrass 100 100 100 100 100 75 100 100 100 Blk Nightshade 95 95 100 95 0 85 100 100 100 Corn G4689A 70 75 50 10 15 20 85 90 65 Cotton 0 0 60 0 0 0 80 60 15 Crabgrass 100 100 100 100 100 100 100 100 100 Fall Panicum 100 100 100 100 100 - Giant Foxtail 100 100 100 100 100 100 100 100 100 Green Foxtail 100 100 100 100 100 100 100 100 100 Johnson Grass 100 100 95 65 60 55 100 70 65 Lambsquarter 95 95 95 95 90 95 95 100 100 Pigweed 100 100 100 100 75 100 95 100 100 Ragweed 100 30 100 90 0 65 100 100 65 Signalgrass 100 100 100 100 100 100 100 100 10O Smartweed - - 100 100 0 55 95 100 90 Soybean 15 20 45 0 0 0 100 100 15 Wild Proso 100 100 100 90 80 95 100 100-100 Wooly Cup Grass 75 100 100 70 80 - 95 85 85 Table D COMPOUND Rate 250 g/ha 32 39 45 56 59 88 109 125 132 PREEMERGENCE Barnyardgrass 70 80 15 100 100 100 Blk Nightshade 90 0 65 95 100 100 Corn G4689A 10 10 0 70 65 40 Cotton 0 0 0 0 25 0 Crabgrass 100 100 75 100 100 100 Fall Panicum 65 100 - Giant Foxtail 100 95 75 100 100 100 Green Foxtail 95 100 100 100 100 100 Johnson Grass 55 60 15 75 70 55 Lambsquarter 90 90 25 95 100 100 Pigweed 90 60 75 80 95 90 Ragweed 45 0 0 100 100 65 Signalgrass 70 100 75 100 100 100 Smartweed 70 0 15 85 100 80 Soybean 0 0 0 60 55 10 Wild Proso 60 80 20 100 100 . 65 Wooly Cup Grass 40 65 - 80 75 75 Wooly Cup Grass - 65 60 60 15 60 - 70 70 60 TEST E Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Indica and Japonica rice ( Oryza sativa) seedlings at the 2.0 to 2.5 leaf stage, seeds selected from barnyardgrass (Echinochloa crus-galli ) , bulrush (Scirpus mucrona tus) , duck salad (Heteranthera limosa) , umbrella sedge ( Cyperus difformis) , and tubers selected from arrowhead (Sagittaria spp.), waterchestnut (Eleocharis spp.), were planted into this soil. After planting, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formu * ;ed in a non-phytotoxic solvent and applied directly t he paddy water. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table E, are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table E COMPOUND Rate 1000 g/ha 88 109 113 PADDY Arrowhead - 100 80 Barnyard 2 Leaf 100 98 100 Barnyardgrass _ _ _ Duck salad 30 100 100 Japonica rice 25 35 50 Umbrella sedge 95 98 90 Waterchestnut 30 40 50 Table E COMPOUND Rate 64 g/ha 14 18 26 88 109 113 PADDY Arrowhead Barnyard 2 Leaf Barnyardgrass Duck salad Japonica rice Umbrella sedge Waterchestnut Table E Rate 32 g/ha PADDY Arrowhead Barnyard 2 Leaf Barnyardgrass Duck salad Japonica rice Umbrella sedge Waterchestnut TEST F Plastic pots were partially filled with silt loam soil. The soil was then flooded with water, Japonica rice (Oryza sativa) sprouted seeds and 1.5 leaf transplants were planted in the soil. Seeds of barnyardgrass (Echinochloa crus-galli) were planted in saturated soil and plants grown to the 1 leaf, 2 leaf and 3 leaf stages for testing. At testing, the water level for all plantings was raised to 2 cm above the soil surface. Chemical treatments were formulated in a non- phytotoxic solvent and applied directly to the paddy water. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table F are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table F COMPOUND Table F COMPOUND Rate 1000 g/ha 88 109 113 Rate 250 g/ha 88 109 113 Flood Flood Jap Direct Seed 25 95 40 Jap Direct Seed 10 45 10 Jap Rice Eff 0 40 35 Jap Rice Eff 0 15 20 2-LF B.Y.Grass 90 95 95 2-LF B.Y.Grass 35 95 85 3-LF B.Y.Grass 45 90 85 3-LF B.Y.Grass 25 80 75 Rate 500 g/ha 88 109 113 Rate 125 g/ha 5 88 109 113 Flood Flood Jap Direct Seed 15 98 25 Jap Direct Seed 95 0 30 0 Jap Rice Eff 0 25 35 Jap Rice Eff 85 0 15 15 2-LF B.Y.Grass 75 98 80 2-LF B.Y.Grass 90 20 85 60 3-LF B.Y.Grass 40 90 90 3-LF B.Y.Grass 80 15 70 45 Table F COMPOUND Table F COMPOUND Rate 64 g/ha 5 88 109 113 Rate 16 g/ha 5 Flood Flood Jap Direct Seed 85 0 10 0 Jap Direct Seed 70 Jap Rice Eff 80 0 10 10 Jap Rice Eff 40 2-LF B.Y.Grass 85 0 45 45 2-LF B.Y.Grass 65 3-LF B.Y.Grass 80 10 30 3-LF B.Y.Grass 65 Rate 32 g/ha 5 Rate 8 g/ha 5 Flood Flood Jap Direct Seed 85 Jap Direct Seed 50 Jap Rice Eff 25 Jap Rice Eff 30 2-LF B.Y.Grass 80 2-LF B.Y.Grass 45 3-LF B.Y.Grass 75 3-LF B.Y.Grass 50 TEST G 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 adjus' ed to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed sp<" -.s include winter barley (Hordeum vulgare cv. 'I. ' ■ ) , bedstraw ( Galium aparine) , blackgrass (Al -jp- ecurus myosuroides) , chickweed (Stellaria media) , downy brome (Bromus tectorum) , field violet ( Viola arvensis) , green foxtail ( Setaria viridis) , kochia (Kochia scoparia) , lambsquarters ( Chenopodium album) , Persian speedwell ( Veronica persica) , rape (Brassica napus cv. 'Jet Neuf), ryegrass (Loliu multiflorum) , sugar beet (Beta vulgaris cv . 'US1'), sunflower (Helianthus annuus cv. 'Russian Giant'), spring wheat (-Triticujn aestivum cv. 'ERA'), winter wheat ( Tri ticum 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 postemergence 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 G, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) means no test result.

Claims: BA-8919-B What is claimed is: 1. A method for controlling the growth of undesired vegetation by applying to the locus to be protected an effective amount of a compound of Formula I: wherein Q is Q-i Q-2 Q-3 Q-4 R is H, C_-C 2 alkyl, C__-C 2 haloalkyl, C- L -C 2 alkoxy, C 2 -C 2 haloalkoxy, C ! -C 2 haloalkylthio, halogen, CN or N0 2 ; Y is NR 7 C(0)XR 3 ; X is a single bond, 0, S or NR 4 ; R 1 is H, C±-Cz alkyl, alkoxy, C_-C 3 haloalkoxy, C_-C 3 alkylthio, C 2 -C 3 alkynyl, C 2 -C 3 alkoxyalkyl, C 2 -C 3 alkylthioalkyl, halogen, N0 2 , CN, NHR 5 or NR 5 R 6 ; R 3 is C 2 -C 5 alkyl optionally substituted with C 1 -C 2 alkoxy, OH, 1-3 halogens, OC(O) (C 1 -C 2 alkyl) or c ι~ 2 alkylthio; CH 2 (C 3 -C 4 cycloalkyl); ^C^ cycloalkyl optionally substituted with 1-3 CH 3 's, 1-2 F's or 1-2 Cl's; C 2 -C 4 alkenyl; C 2 -C 4 haloalkenyl; C 3 -C 4 alkynyl; C(0) (C 1 -C 2 alkyl); benzyl; or a 5- or 6-membered heterocyclic ring containing one heteroatom selected from 0, N and S, each ring optionally substituted with halogen or CH 3 ; R 4 is H, C 1 -C 2 alkyl or 0CH 3 ; R 5 and R 6 are independently C 1 -C 2 alkyl; R 7 is H, C 1 -C 2 alkyl or C(0)R 8 ; R 8 is Cx-Cs alkyl optionally substituted with C_-C 2 alkoxy, OH, 1-3 halogens, OC(0) (C 1 -C 2 alkyl) or C x -C 2 alkylthio; CH 2 (C 3 -C 4 cycloalkyl); C 3 -C 4 cycloalkyl optionally substituted with 1-3 CH 3 's, 1-2 F's or 1-2 Cl's; C 2 -C 4 alkenyl; C 2 -C haloalkenyl; C 3 -C 4 alkynyl; C(0) (C 1 -C 2 alkyl); benzyl; or a 5- or 6-membered heterocyclic ring containing one heteroatom selected from 0, N and S, each .ring optionally substituted with halogen or CH 3 ; and n is 0 or 1; provided that when R 3 is C 2 alkenyl, C 2 haloalkenyl or a heterocyclic ring then X is a single bond. 2. The method of Claim 1 wherein R is C 1 -C 2 haloalkyl, C 1 -C 2 haloalkoxy, C 1 -C 2 haloalkylthio, halogen or CN. 3. The method of Claim 2 wherein R 1 is C x -C alkyl, ^-^ alkoxy, C 2 -C 2 alkylthio, C 2 -C 3 alkoxyalkyl, C 2 -C 3 alkylthioalkyl, Cl, Br, CN, NHR 5 or NR 5 R 6 ; and R 7 is H. 4. The method of Claim 3 wherein Q is Q-l or Q-2; and R 3 is C_-C 4 alkyl optionally substituted with c ι~ c 2 alkoxy; CH 2 (C 3 -C 4 cycloalkyl) ; C 3 -C 4 cycloalkyl optionally substituted with 1-3 CH 3 's; or C 2 -C 4 alkenyl. 5. The method of Claim 4 wherein R is C x -C 2 fluoroalkyl, C 1 -C fluoroalkoxy, C j^ -Ca fluoroalkylthio, Cl, Br or CN. 6. The method of Claim 4 wherein Formula I is 1- methylethyl [5-methyl-3'-(trifluoromethyl) [1,1'- biphenyl]-2-yl]carbamate. 7. The method of Claim 4 wherein Formula I is 3- methyl-N-[5-methyl-3'-(trifluoromethyl) [1,1'-biphenyl]-2- yl]butana ide. 8. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of any of Claims 1-7 with the further proviso that when Q is Q-l, R 1 - is H and Y is NHC(0)CH 3 , then R is other than Br or F, and at least one of the following: surfactant, solid or liquid diluent. 9. A compound of Formula I of any of Claims 1-7 with the further proviso that when Q is Q-l, R 1 is H and Y is NHC(0)CH 3 , then R is other than Br or F.

Inventors: DENES LUCIAN RADU, DENES, LUCIAN, RADU
Applicants: DU PONT, E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1992
Main classification: C07C271
IPC codes: A01N37, A01N43, A01N47, A01N53, C07C233, C07C235, C07C255, C07C271, C07C275, C07C323, C07D213, C07D307, C07D333