HERBICIDAL ARYL TRIAZOLINONES

Abstract: Herbicidal aryl triazolinones include the compounds of formula (I), where X is preferably halogen such as fluorine, Y is preferably halogen such as chlorine, R<1> is preferably methyl, R<2> is preferably CHF2, R<3> is preferably CH(CH3). Z is oxygen or sulfur. R<4> may be alkyl, substituted alkyl, alkenyl, alkynyl, monovalent cyclic having a ring of 5 or 6 atoms or ZR<4> may be a residue of an amine, a sulfonamide, or an oxime.

Description: HERBICIDAL ARYL TRIAZOLINONES The invention described in this application per- _ tains to weed control in agriculture, horticulture, and other fields where there is a desire to control unwanted plant growth. More specifically, the present application describes certain herbicidal aryl tria- zolinones, compositions of them, methods of preparing them, and methods for preventing or destroying unde- sired plant growth by preemergence or postemergence application of the herbicidal compositions to the locus where control is de j sired. The present compounds may be used to effectively control a variety of both grassy and broadleaf plant species. ' The present invention is particularly useful in agriculture; a number of the compounds described herein show a selec¬ tivity favorable to certain crops at application levels which inhibit the growth of or destroy a variety of weeds. One aspect of this invention relates to herbici¬ dal compounds of the general formula (Formula I) wherein R is CHF, or CH-F; X is bromine, chlorine, or fluorine or haloalkyl (e.g. CF-); R 1 may be halogen (e.g. chlorine), alkyl (e.g.. of 1 to 5 carbon atoms), haloalkyl (e.g. of 1 to 5 carbon atoms such as difluoromethyl) , alkoxyalkyl (e.g. of 2 to 6 carbon atoms such as methoxymethyl) , cyanoalkyl (e.g. of 2 to 6 carbon atoms such as cyano- methyl), arylalkyl such as benzyl, alkylthio (e.g. of 1 to 3 carbon atoms such as methylthio) or the corre¬ sponding alkylsulfinyl or alkylsul onyl, or alkylthio- alkyl (e.g., . of 1 to 3 carbon atoms independently with respect to each alkyl, such as methylthiomethyl) or the corresponding alkylsul inylalkyl or alkylsulfonyl- alkyl. Y is bromine, chlorine, fluorine, methyl, haloalkyl (e.g. FCH-), a radical of the formula R 8 OCH 2 -, R 8 SCH 2 -, R 8 S0CH-- or R 8 S0 2 CH 2 ~ where R 8 is C.-C j alkyl, C 2 -C 5 alkenyl, or C 3 - ( _ 5 alkynyl (e.g., CH 3 OCH 2 -, CH.-SCH--, CH 2 =CHCH 2 OCH 2 -, CH 2 =CHCH 2 SCH 2 -, CH≡CCH 2 OCH 2 -, or CH≡C-CH 2 SCH 2 -) ; R- may also be phenyl (or phenyl substituted with e.g., halogen, alkyl, haloalkyl; see, e.g. compound 50, below). R is an alkylene radical (e.g. a lower alkyl- ene such as "CH 2 - or -CH(CH_.)-) or a haloalkylene radical (e.g. -CHF-) and R is an alkyl radical (e.g. CH 3 , C 2 H 5 , C 3 H 7 , C^). It is preferred that R be methyl and R be CHF- and particularly that X be chlorine or (more preferably) fluorine and Y be chlorine. Some of the compounds described above differ from otherwise similar compounds disclosed in U.S. patent 2 4,318,731 in that R of that patent is hydrogen, an alkyl group, or an alkenyl group. It has been found now that the replacement of an alkyl group by a CHF- or CH-F group yields compounds of much greater herbicidal activity. . This is shown, for instance, in Table I below which gives the results of tests of the following two compounds, each applied at the rate of 0.125 kg. per hectare: 2 A. A compound in which R is CHF 9 (compound No. 5 described below). B. An otherwise identical compound in which 2 R is 2 H- (compound 62 of the aforesaid U.S. patent). Representative compounds according to this aspect of the invention are given in Table 2 below. The herbicidal esters of the aspect of the inven¬ tion described above may be hydrolyzed to produce the corresponding acids, i.e., to compounds of the fore¬ going formula in which the substituent para to "X" is -OR COOH (i.e. carboxyalkoxy) . I have found that these acids are also effective herbicides, somewhat less potent than the corresponding esters. The acids are also useful as intermediates for the preparation (as by esteri ication or amide formation) of other herbicidal compounds.* The acids may be converted to their salts, such as their sodium, potassium, ammo¬ nium, calcium, magnesium, or mono, di or trialkylammo- nium salts, which may be used as herbicides. Representative acids and salts are shown in Table 3 below. In another aspect of this invention it has now been found that compounds of the following formula are effective herbicidal compounds: (Formula II) wherein R is a substituted alkyl group, an alkenyl group (e.g. allyl or methallyl) or an alkynyl group (e.g., propargyl) or a monovalent cyclic group having a ring of 5 or 6 atoms (e.g. an aromatic or hetero- cyclic or alicyclic ring) whose valence is on a carbon atom of said ring, and Z is 0 or S. Corresponding 4 compounds in;which Z is sulfur and R is unsubsti- tuted alkyl (e.g. of 1-4 carbon atoms) have also been found to be effective herbicides. With respect to R , examples of suitable substituents on the alkyl group are: nitro; halo (Cl,F,Br); furyl or tetrahydrofuryl ; acetyl (CH.-C0); -C0-N(R π )(R πI ) where -N(R H )(R 111 ) is the residue (minus hydrogen) of ammonia or of a pri¬ mary or secondary amine (e.g. methylamine, di ethyl- amine or other lower alkylamine) ; cyano; -C00R IV where RIV is the residue of an alco¬ hol (such as the residue of a lower alkanol, e.g. a methyl or ethyl radical) ; phenyl or substituted phenyl; alkylamino, dialkylamino or a trialkylammonium salt (such as that shown in compound no. B20 below); alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl (in which radicals the alkyl is preferaby methyl or other lower alkyl) or phenoxy, phenylthio, phenylsul- finyl, or phenylsulfonyl (in which radicals the phenyl moiety may be substituted or unsubstituted) . 4 When R is alkenyl or alkynyl it may be substi¬ tuted with one of the foregoing substituents. For the substituted phenyls mentioned above the substituents may be, for instance, alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, halogen, cyano, nitro, hydroxy, amino or alkyl or dialkylamino or carboxyl. It is preferred that X, Y, R 1 and R2 be as defined above for Formula I, and particularly that X be chlorine or (more preferably) fluorine, Y be chlo- rine, R 1 be methyl and R2 be CHF_. However, within the broader scope of this aspect of the inven- tion R substituents may be alkyl (e.g. of 1 to 5 carbon atoms), haloalkyl (e.g. of 1 to 5 carbon atoms, such as CHF-), alkenyl of 2 to 5 carbon atoms (e.g. allyl), alkynyl of 3 to 5 carbon atoms (e.g. pro- pargyl), cyanoalkyl (e.g. CH 2 CN or CH 2 CH 2 CN) , thio- cyanoalkyl (e.g. CH-SCN) or a group of the formula -alkylene-Y 1-R5 in which said alkylene group (e.g. -CH,-) has 1 to 5 carbon atoms, Y being oxygen or S(0) in which r is 0 to- 2, and R 5 being alkyl (e.g. o 1 to 5 carbon atoms such as methyl), alkenyl of 2 to 5 carbon atoms (e.g. allyl) or alkynyl of 3 to 5 carbon atoms (such as propargyl). Representative compounds according to this aspect of the invention are shown in Table 4 below. In still another aspect of this invention i.t has now been found that compounds of the following formula are effective herbicidal compounds: (Formula III) in which R is an alkylene radical (e.g. -CH-- or -CH(CH j )-) or a haloalkylene radical (e.g. -CHF-), and -N y 7 is -NH., or the residue of a primary or secondary am.irie or of a sulfonamide. For instance, ή 7 R and R may be, each, independently, H, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, alkoxy, alkylsul- fonyl, haloalkylsulfonyl , cycloalkylsul onyl, arylsul- fonyl (including heteroarylsulfonyl such as thienyl- sulfonyl), aralkylsul onyl, a inosulfonyl, dialkyl- aminosul onyl, alkylaminosulfonyl, alkenylsulfonyl, phenylalkenylsulfonyl. R may be bicyclic or poly- cyclic such as benzofuranyl, dihydrobenzo uranyl benzo uransulfonyl, dihydrobenzo uransulfonyl, naphthalenesulfonyl, benzόdioxosul onyl, anthraquin- (s 7 onesulfonyl. Any of R , R may carry one or more substituents such as halogen, nitro, amino, alkoxy, alkyl, haloalkgxy, alkenyloxy, haloalkenyloxy, alkoxy- alkoxy, alkoxyalkylthio, cyano, aminocarbonylox , alkylaminocarbonyloxy or dialkylaminocarbonyloxy, acyla ino, alkoxycarbonyl, aminocarbonyl, alkylamino- carbonyl, dialkylaminocarbonyl or hydroxycarbonyl (but (s 7 when one of R , R is connected to the nitrogen of formula II an oxygen or sulfur atom, then the other of R is H or a group connected to that nitrogen by a carbon-nitrogen linkage or a salt-form- f 7 ing group, such as indicated below). R and R may together comprise a divalent group, such as an alkylene or haloalkylene or alkyloxyalkylene group or thioether, or its corresponding sulfine or sulfone, f*. 7 (e.g. such that NR R together comprise a pyrroli- dino, piperidino, morpholino, or thiazolidino ring), any of which may also carry a carboxylic ester or amide substituent. The salt-forming group (e.g. when R is alkylsul onyl, cycloalkylsulfonyl or aryl- sulfonyl) may be a metal (e.g. Na, K or Ca) or ammo- nium (e.g. NH. or lower alkyl-substituted ammo- (s 7 nium). R and R may comprise a divalent group such that NR together constitute, for instance, 0 a saccharin ring structure, e.g. -N JO) • which is an active herbicide (such as compound C62 below) and which upon hydrolysis, can lead to other active herbi¬ cides such as compounds C58 and C59. Compound C62 for example is obtainable by reac- 0 tion of saccharin HN Tθ_ with the appropriate acid chloride. In this (Formula III) aspect of the invention, X, Y and R may be as defined above for Formula I, and 2 R may be as defined above for Formula II. It is preferred that R 1 be methyl and R2 be CHF 2 and particularly that X be chlorine or (more preferably) fluorine and Y be chlorine. Representative compounds according to this aspect of the invention are shown in Table 5 below. Still another aspect of this invention relates to herbicidal compounds of the formula (Formula IV) where -OR is the residue of an oxime, such as a ketoxime of the formula each alkyl group preferably being lower alkyl such as 1 2 methyl. X, Y, R and R have the meanings given in connection with Formula I (for X, Y and R ) and Formula II (for R ). Preferably X is chlorine or (more preferably) fluorine, Y is chlorine, R is 2 methyl and R is CHF-; in some typical compounds CH. of this kind the radical OR 3 COOR 9 is -0CH(CH^)C00N=C ,SCH 3 ' ^CH. X is fluorine, Y is chlorine, R is methyl and R2 is CHF 2 ; other typical compounds are ide.ntical with those except that Y is Br or CF,. Compounds of Formula IV may be prepared by reacting the corresponding acid chloride (i.e. the compound in which the substituent at the 5-position of the benzene ring is -OR C0C1) with the corresponding oxime in the presence of an acceptor for HC1 such as triethylamine or sodium carbonate or sodium hydroxide. In each aspect of the invention, it is often pre¬ ferable that any alkyl, alkenyl, alkynyl or alkylene radical have less than 6 carbon atoms, The compounds of this invention may be prepared by methods generally described in the literature or by methods analogous or similar thereto and within the skill of the art. One type of method starts with an intermediate in which the substituent para to "X" is hydroxyl. For instance, one may use the intermediate described in "Synthetic Process Example 6" of UK patent application GB 2 090 250 published 7 July 1982, in which X and Y are Cl, R1 is CH, and R2 is CHF 2 (the corresponding compound in which R 2 is CH 2 F is made by substituting chlorofluoromethane for the chlorodi luoromethane used in "Synthetic Process Example 1" of ? that published patent application). The OH group of the intermediate may then be converted to the desired substituent, as by a conventional etheri- fication reaction, e.g., by reacting it with the appropriate bromide in the presence of a known accep¬ tor of HBr such as NaH or a mixture of K 2 C0 3 and Nal. As illustrated in Examples 2 and 3 below, the synthesis may employ a substituted phenylhydrazine, whose hydrazine portion is then modified to form a triazolinone ring. Such modification (which in Examples 2 and 3 is effected by reaction with pyruvic acid and then with a phosphoryl azide) may also be effected by other techniques, such as by treating the substituted phenylhydrazine with any of the following four types of reagents: (a) an inner salt of a 3-(l-iminoalkylmer- capto)-1-propanesulfonic acid (which may be prepared according to Reid and Schmidt, Ann. Chem. 676, 114 (1964) from 1,3-propanesultone and a thioamide), to form an amidrazone followed by reaction with a source of phosgene, as by the following reaction sequence (which is also illustrated in Example 15 below), amidrazone in hich "Ar" is aromatic as described below. (b) .An imidate ester of the formula ΘNH 2 CIΘ R c c _ 0 R<i to form the corresponding amidrazone (as described, for instance, in the article by Neilson et al "The Chemistry of Amidrazones: Chem. Rev. _7_! > 151(1970) at page 156), followed by reaction with a source of phos- gene, as in (a) above, Rc. and Rd being alkyl or other suitable radical. (c) A compound of the formula (where Ra and Rb are lower alkyl) in the presence of a base according to the following sequence: in which R 1 (d) A haloalkylnitrile (e.g. a fluoroalkyl, fluorochloroalkyl or fluorobromoalkyl nitrile such as CICF^CN, followed by reaction with a source of phos¬ gene, so that the reaction may proceed along the following lines, for instance (and as also illustrated in Example 16 below), to form the aryl 3-haloalkyl triazoline, thus: NH 2 ArNHNH 2 + C1CF 2 CN — ■ •—-> ArNH-N-C-CF 2 Cl > Ar-N XN-H CH3OH Cl 3 COCCl N « . ππ CF 2 C1 o O or C0C1 2 In Examples 2 and 3 below the "Ar" portion of the aryl hydrazine (whose hydrazine portion is then modi¬ fied to form the triazoline ring) has halo substi- , tuents at its 2 and 4 positions and an alkoxy group at its 5 position. Instead, in each of the processes illustrated above (and in the process of those Examples 2 and 3), the Ar ' group may be a phenyl radical or a fluorophenyl (e.g. 2-fluorophenyl) or a nitrophenyl (e.g. 3-nitrophenyl) alkoxyphenyl (e.g. 3-methoxyphenyl) or, most preferably, halonitrophenyl, particularly a .fluoronitrophenyl (such as 2-fluoro-5- nitrophenyl) or haloalkoxyphenyl (such as 2-fluoro-5- alkoxyphenyl) and the aryl triazoline may then be treated to (a) alkylate the nitrogen at the 4-position of the triazoline ring (in known manner, e.g. with an alkyl or fluoroalkyl halide, such as with C1CHF 2 to add the preferred - CHF 2 substituent) and (b) to introduce additional substituents onto the aromatic ring, as by halogenation with chlorine or bromine (e.g. by reacting with Cl 2 , Br 2 or S0 2 C1 2 ). For instance the alkylation of the nitrogen at the 4-position may be effected first, after which the nitro group (if present) may be reduced to an amino group in conventional manner, the amino group may be converted to a hydroxyl group (as by conventional diazotization) and then, preferably after etherifying the OH to form an alkoxy (e.g. methoxy) group, the compound may be halogenated as above to place the halogen substituent or substituents on its benzene ring. The resulting compound may then be modified at the 5-position of the benzene ring to form the herbi¬ cidal compounds of. this invention. ■ For instance,, for making the preferred compounds of the invention in which the benzene ring has a 2-fluoro substituent, the starting material may be 2-fluoro-5-nitrophenylhydra- zine, .which may be treated as described above to pro¬ duce successively a series of novel compounds such as l-(2-fluoro-5-nitrophenyl)-4, 5-dihydro-3-methyl-l, 2,4- triazol-5(lH)-one, then l-(2- luoro-5-nitrophenyl-4, 5- dihydro-4-difluoromethyl-3-methyl-l,2, 4-triazol-5(lH)- one. These may be converted to the corresponding novel compounds having, a-t the 5-position of the benzene ring, successively * - NH 2 , -OH and (prefer¬ ably) - 0CH_., followed by halogenation to place, for instance, a chloro or bromo substituent at the 4-posi- tion of the. benzene ring. Instead of alkylating at the 4-position of the ring triazoline at an early stage, e.g. prior to altering the nitro group, this alkylation step may be delayed until after the above- described halogenation of the benzene ring or even until after the conversion of the alkoxy (or other) group at the 5-position of the benzene ring to one of the groups described at that position in Formulas I, LI, III and IV (and Tables 2, 3, 4, and 5) above. Similarly, when the reagent(s) used to react with the aryl hydrazine are such as to produce a triazolin- one having a haloalkyl (e.g. CHF 2 ) group instead of an alkyl group on the carbon at the 3-position of the heterocyclic ring, the series of new compounds will include, successively, (from 2-fluoro-5-nitrophenyl hydrazine) such compounds as l-(2-fluoro-5-nitro- phenyl)-4, 5-dihydro-3-difluoromethyl-1,2,4-triazol-5- (lH)-one, then l-(2-fluoro-5-nitrophenyl)-4, 5-dihydro- 4-methyl (or difluoromethyl)-3-difluoromethyl-1, 2, 4- triazol-5(lH) -one. These may be converted to the corresponding novel compounds having, at the 5-posi- tion of the bepzene ring, successively - NH-, -OH and (preferably) -0CH 3 followed by halogenation to place, for instance, a chloro or bromo substituent at the 4-position of the benzene ring. When the aryl hydrazine is 3-nitrophenyl hydrazine (instead of 2-fluoro-5-nitrophenylhydrazine) the series of novel compounds will include, successively, such compounds as l-( 3-nitrophenyl) -4, 5-dihydro-3-difluoromethyl- 1 , 2, 4-triazol-5(lH) -one, then l-(3-nitrophenyl) -4, 5- dihydro-4-methyl (or difluoromethyl) -3-difluoro- methyl-1 , 2 , 4-triazol-5( 1H-) -one. These may be con¬ verted to the corresponding novel compounds having, at the 3-position of the benzene ring, successively - NH 2 , -OH and (preferably) -0CH 3 , followed by halo¬ genation to place, for instance, chloro or bromo sub¬ stituents on the benzene ring. Example 11 below illustrates a process for making a compound of this invention having a sulfonamide group at the 5-position of the benzene ring by react¬ ing (a) a compound having an oxypropionic acid substi¬ tuent at that 5-position with (b) an aryl sulfonyliso- cyanate. Another method for introducing the sulfonamide group is by reacting (a) a compound having a phenolic OH group at that 5-position with (b) an N-aryl (or alkyl etc.) sulfonylalkanoic acid amide having a reactive leaving substituent (e.g. Br, Cl, mesylate or tosylate) on the alkane portion of the molecule, e.g. 0 II CH 3 CHC-NHS0 2 Ar. Br Such a reaction can be carried out in the presence of a base (e.g. in acetone in the presence of sodium or potassium carb-onate). This method is illustrated in Example 14 below. The following Examples illustrate the preparation of the compounds of this invention. Example 1 Ethyl [2, 4-dichloro-5-(4-di luoromethy1- 4, 5-dihydro-3-methyl-5-oxo-lH-l,2,4-triazol- l-yl)phenoxy]acetate To a stirred mixture of 15.0 g (0.048 mole) of l-(2,4- dichloro-5-hydroxyphenyl)-4-difluoromethyl-4, 5-dihydro- 3-methyl-l,2, 4-triazol-5( ' lH)-one and 3.4 g (0.024 mole) of potassium carbonate in 100 L of acetone was added 8.1 g (0.048 mole) of ethyl bromoacetate. The resultant mixture was stirred at reflux for three hours. After cooling, the mixture was evaporated under reduced pressure leaving a residue. This residue was partitioned between diethyl ether and water. The organic phase was washed with an aqueous 10. sodium hydroxide solution, then was dried over anhydrous magnesium sulfate and filtered. Evaporation of the filtrate under reduced pressure produced 17.8 g of a solid. A small portion of this solid was recrys- tallized from methanol and water to yield ethyl [2,4- dichloro-5-( 4-difluoromethyl-4, 5-dihydro-3-methyl-5- oxo-lH-1,2, 4-triazol-l-yl)phenoxyjacetate (mp 118- 119°C), compound 17. The nmr spectrum was consistent with the proposed structure. The following compounds were also prepared by the process of Example 1 from l-(2, 4-dichloro-5-hydroxy- phenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-l,2,4- triazol-5(lH)-one; l-(4-chloro-2-fluoro-5-hydroxy- phenyl)-4-di luoromethyl-4, 5-dihydro-3-methyl-l,2,4- triazol-S(lH)-one ; 2-[2, 4-dichloro-5-(4-difluoromethy1 4,5-dihydro-3-methyl-5-oxo-lH-l,2, 4-triazol-l-yl)- phenoxyjpropionic acid, compound Al ; or 2-[4-chloro- 2-fluoro-5-(4-difluoromethyl-4, 5-dihydro-3-raethyl-5- oxo-.lH-l,2, 4-triazol-l-yl)phenoxyJpropionic acid, compound A2, and one of the following: Compound Reagent 14 methyl bromoacetate 17 ethyl bromoacetate 19 tert-butyl 2-bromopropionate 21 tert-butyl bromoacetate 22 tert-butyl bromoacetate B6 l-methyl-2-propynyl 2-bromopropionate B7 ϊ, l-dimethyl-2-propynyl 2-chloropropionate Bll bromoacetonitrile B16 -brorao-γ-butyrolactone B22 chloromethyl methylether B23 chloromethyl methylsulfide Cl iodoacetamide C7 iodoacetamide C9 N-(l-methylpropyl) 2-bromopropionamide Example 2 2-[2-Chloro-4-fluoro-5-(4-difluoromethy1- 4, 5-dihydro-3-methyl-5-oxo-lH-l,2, 4-triazol- l-yl)phenoxyJpropionic acid Step A 4-Chloro-2-fluoro-5-methoxyaniline from 2-chloro-4-fluorophenol The intermediate 4-chloro-2- luoro-5-methoxyaniline was prepared in a five step synthesis from commer¬ cially available 2-chloro-4-fluorophenol as detailed by E. Nagano, et al. in European Patent Application 69,855. Step B 4-Chloro-2-fluoro-5-methoxyphenylhydrazine A stirred solution of 48.0 g (0.27 mole) of 4-chloro- 2-f ' luoro-5-methoxyaniline in 500 mL of concentrated hydrochloric acid was cooled to -5°C and 23.5 g (0.34 mole) of sodium nitrite in 100 mL of water was added dropwise. After complete addition the reaction mix¬ ture was stirred at 0°C for one hour. A second solu¬ tion of 154.0 g (0.68 mole) of stannous chloride in 225 mL of concentrated hydrochloric acid was cooled to 0°C, and the cold diazonium solution prepared above was added to it slowly. After complete addition the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was filtered to collect a solid. This solid was dissolved in an aqueous 50% sodium hydroxide solution and the solution extracted with toluene. - The toluene extract was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 22.4 g of 4-chloro-2- luoro-5-methoxyphenylhydrazine as a solid. The nmr spectrum was consistent with the proposed structure. Step C Pyruvic acid, 4-chloro-2-fluoro-5-methoxy- phenylhydrazone A stirred solution of 21.0 g (0.11 mole) of 4-chloro- 2-fluoro-5-methoxyphenylhydrazine and 100 mL of aqueous 10% hydrochloric acid in 100 mL of ethanol was warmed to 40°C, and a solution of 10.0 g (0.114 mole) of pyruvic acid in 20 mL of water was added. Upon complete addition the reaction mixture was stirred for one hour. An additional 50 mL of -water was added and the reaction mixture filtered to collect a solid. The solid was air dried to yield 29.0 g of pyruvic acid, 4-chloro-2-fluoro-5-methoxyphenylhydrazone; mp 166- 169°C. The nmr- spectrum was consistent with the proposed structure. Step D l-(4-Chloro-2-fluoro-5-methoxyphenyl)-4, 5- dihydro-3-methyl-l, 2,'4-triazol-5(lH)-one A stirred solution of 27.0 g (0.104 mole) of pyruvic acid, 4-chloro-2-fluoro-5-methoxyphenylhydrazone, 29.0 g (0.105 mole) of diphenyl phosphoryl azide, and 11.0 g (0.108 mole) of triethylamine in 500 mL of toluene was heated under ' reflux for four hours. The reaction mixture was cooled to ambient temperature and extracted with an aqueous 10% sodium hydroxide solu¬ tion. The extract was neutralized with gaseous carbon dioxide, and a solid was collected by filtration. The solid was air dried to yield 11.0 g of l-(4-chloro- 2-fluoro-5-methoxyphenyl)-4, 5-dihydro-3-methyl-l,2,4- triazol-5(lH)-one; mp 193-195°C. The nmr spectrum was consistent with the proposed structure. Step E l-( 4-Chloro-2-fluoro-5-methoxyphenyl)-4, 5- dihydro-4-di luoromethyl-3-methyl-l,2,4- triazol-5(lH)-one A stirred mixture of 10.0 g (0.039 mole) of l-(4- chloro-2-fluoro-5-methoxyphenyl)-4, 5-dihydro-3-methy1- 1, 2, 4-triazol-5(lH)-one, 10.0 g (0.031 mole) of tetra- butylammonium bromide and 10.0 grams (0.25 mole) of sodium hydroxide in 250 L of cyclohexane was warmed to 60°C. Chlorodifluoromethane (10.0 g, 0.12 mole) was bubbled into the reaction mixture. After complete addition the reaction mixture was warmed to reflux where it stirred for one hour. The hot solution was decanted from a pot residue and cooled to ambient temperature.*; Methylene chloride was added to the cooled mixture , to dissolve a solid precipitate. The mixture was washed with 10% hydrochloric acid then with an aqueous 10% sodium hydroxide solution. The organic layer was dried with anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 5.0 g of l-(4-chloro- 2-fluoro-5-methoxyphenyl)-4-difluoromethyl-4, 5-dihydro- 3-methyl-l, 2, 4-triazol-5(lH)-one; mp 86-88°C. The nmr spectrum was consistent with the proposed structure. Step F l-(4-Chloro-2- luoro-5-hydroxyphenyl)-4- difluoromethyl-4, 5-dihydro-3-methyl-l,2,4- triazol-5(lH)-one " A stirred mixture of 4.6 g (0.015 mole) of l-(4- chloro-2-fluoro-5-methoxyphenyl) -4-difluoromethyl-4, 5- dihydro-3-methyl-l, 2, 4-triazol-5(lH)-one in 200 mL of methylene chloride was cooled to 10°C and a solution of 11.2 g (0.045) mole of boron tribromide in 45 mL of methylene chloride was added. Upon complete addition the reaction mixture was stirred for four hours as it warmed to ambient temperature. After this time 100 mL of water was added, and stirring was continued for an additional 18 hours. The organic layer was separated, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to yield 4.4 g of l-(4-chloro-2-fluoro-5-hydroxy- phenyl)-4-di luoromethyl-4, 5-dihydro-3-methyl-l,2,4- triazol-5(lH)-one; mp 147-152°C. The nmr spectrum was consistent with the proposed structure. Step G Methyl 2-[2-chloro-4-fluoro-5-(4-di luoro¬ methyl-4, 5-dihydro-3-methyl-5-oxo-lH- 1,2, 4τtriazol-l-yl)phenoxy]propionate To a stirred mixture of 1.5 g (0.0051 mole) of l-(4- chloro-2- luoro-5-hydroxyphenyl)-4-di luoromethyl-4, 5- dihydro-3-methyl-l,2,4-triazol-5(lH)-one and 0.12 g (0.0051 mole) of sodium hydride in 50 mL of N,N-di- methylformamide was added 0.85 g (0.0051 mole) of methyl 2-bromopropionate. After complete addition the reaction mixture was heated at reflux for two hours, then cooled to room temperature and stirred for approximately 18 hours. The solvent was removed by evaporation under reduced pressure leaving a residue. This residue was partitioned between diethyl ether and water. The organic phase was washed with an aqueous 10% sodium hydroxide solution. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 1.5 g of methyl 2-[2-chloro-4- luoro-5-(4-di- fluoromethyl-4, 5-dihydro-3-methyl-5-oxo-lH-l,2,4-tria- zol-l-yl)phenox jpropionate as an oil, Compound 3. The nmr spectrum was consistent with the proposed structure. The following compounds were also prepared by the process of Example 2, Step G, from l-(2, 4-dichloro-5- hydroxyphenyl)-4-difluoromethyl-4, 5-dihydro-3-methyl- l,2,4-triazol-5(lH)-one; l-(4-chloro-2-fluoro-5- hydroxyphenyl)-4-difluoromethyl-4, 5-dihydro-3-methyl- 1, 2, 4-triazol-5(lH)-one; or compound A2 and one of the following reagents: Compound Reagent 1 methyl bromoacetate 2 methyl 2-bromopropionate 5 ethyl 2-bromopropionate 6 ethyl 2-bromopropionate 18 ethyl 4-bromopropionate 20 ethyl 2-bromoisobutyrate B21 N,N-diethyl-2-chloroacetamide C8 N,N-diethy1-2-chloroacetamide Step H 2-[2-Chloro-4-fluoro-5-(4-difluoro- methyl-4, 5-dihydro-3-methyl-5-oxo-lH- - 1,-2, 4- ' triazol-l-yl)phenoxyJpropionic acid A stirred mixture of 1.3 g (0.0034 mole) of methyl 2-[2-chloro-4-fluoro-5-(4-difluoromethyl-4, 5-dihydro- 3-methyl-5-oxo-lH-l, 2, 4-triazol-l-yl)phenoxyJpro- pionate and 1.0 g (0.018 mole) of potassium hydroxide in 15 L of ethanol and 15 mL of water was heated at reflux for three hours. The mixture was allowed to cool to room temperature and stand for two days. The solvent was evaporated from the mixture leaving a solid. This solid was dissolved in water, and the solution was made acidic with concentrated hydro¬ chloric acid. This solution was extracted with methylene chloride. The extract was dried over anhy¬ drous magnesium sulfate and-filtered. Evaporation of the solvent from the filtrate left 0.85 g of 2-[2- chloro-4-fluoro-5-( 4-difluoromethyl-4, 5-dihydro-3- methyl-5-oxo-lH-l,2, 4-1riazol-1-yDphenoxyJpropionic- acid as a solid (mp 50-55°C), Compound A2. Compound Al was also prepared by the method of Example 2, Step H, from Compound 2. Example 3 2-[ 4-Chloro-5-(4-difluoromethyl-4, 5-dihydro- 3-methyl-5-oxo-lH-l,2, 4-triazol-l-yl)-2- methylphenoxyJpropionic acid Step A 4-Methyl-3-methoxyphenylhydrazine A stirred mixture of 100.0 g (0.73 mole) of 4-methyl- 3-methoxyaniline in 800 mL of concentrated hydrochlo¬ ric acid was cooled to -5°C. A solution of 501.5 g (0.73 mole) of sodium nitrite in 250 mL of water was added slowly while maintaining the temperature of the reaction mixture below 0°C. The resultant mixture was stirred at; -5°C for 30 minutes. A cold solution of 330.0 g (1.46 mole) of tin (II) chloride dihydrate in 360 mL of concentrated hydrochloric acid was added over one hour. After complete addition the resultant mixture was allowed to warm to room temperature. A solid precipitate formed and was collected by filtra¬ tion and stirred in 200 mL of water. This mixture was neutralized with 50% aqueous sodium hydroxide, and extracted with toluene. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 58.0 g of 4-methyl-3-methoxyphenylhydrazine as an oil. The nmr spectrum was consistent with the pro- • posed structure. Step B Pyruvic acid, 4-methyl-3-methoxyphenyl- hydrazone To a stirred mixture of 57.6 g (0.378 mole) of 4-methyl-3-methoxyphenylhydrazine in 400 L of ethanol and 400 mL of IN hydrochloric acid was added 33.3 g (0.0378 mole) of pyruvic acid. After complete addition the mixture was stirred at room temperature for one hour, and 1 liter of water was added. The mixture was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 59.0 g of pyruvic acid, 4-methyl-3-methoxyphenylhydrazone. The nmr spectrum was consistent with the proposed structure. Step C 4, 5-Dihydro-l-(4-methyl-3-methoxyphenyl)- 3-methyl-l,2,4-triazol-5(lH)-one To a stirred: mixture of 56.8 g (0.26 mole) of pyruvic acid, 4-methyl-3-methoxyphenylhydrazone in 1500 L of toluene was added 25.9 g (0.26 mole) of triethyl- amine. The mixture was heated at 50°C, and 70.3 g (0.26 mole) of diphenyl phosphoryl azide was added. The resultant mixture was heated at reflux for approximately 18 hours. The mixture was cooled and extracted with four 200 mL portions of an aqueous 10% sodium hydroxide solution. The aqueous extracts were combined, washed with toϊuene, and made acidic. The resultant solid was collected by filtration and air dried to yield 75.0 g of 4, 5-dihydro-l-(4-methyl-3- methoxyphenyl)-3-methyl-l,2,4-triazol-5(lH)-one (mp 164-168°C). The nmr spectrum was consistent with the pro¬ posed structure. Step D 4-Difluoromethyl-4, 5-dihydro-l-(4-methyl- 3-methoxyphenyl)-3-methyl-l, 2, 4-triazol- 5(lH)-one A stirred mixture of 60.0 g (0.28 mole) of 4,5-di- hydro-l-(4-methyl-3-methoxyphenyl)-3-methyl-l,2,4- triazol-5(lH)-one, 60.0 g (0.19 mole) of tetrabutyl- ammonium bromide and 60.0 g (1.5 mole) of powdered sodium hydroxide in 2 liters of cyclohexane was heated at reflux. During a two hour period 60.0 g (0.67 mole) of gaseous difluorochloromethane was bubbled into the mixture. After complete addition the mixture was stirred at reflux for one hour, then allowed to cool to 70°C. The supernatant liquid was decanted and washed with aqueous 10% hydrochloric acid followed by an aqueous 10% sodium hydroxide solution. The organic layer was dried with magnesium sulfate and filtered. The filtrate was evaporated under reduced-pressure to leave a solid. This solid was triturated with petroleum ether and filtered. The filter cake was air dried to yield 18.5 g of 4-difluoromethyl-4, 5-dihydro-l-(4-methyl-3-methoxy- phenyl)-3-methyl-l,2, 4-triazol-5-(lH)-one. The nmr spectrum was consistent with the proposed structure. Step E l-(2-Chloro-4-methyl-5-methoxyphenyl)- 4-difluoromethyl-4, 5-dihydro-3-methyl- 1,2, 4-triazol-5(lH)-one A solution of 15.0 g (0.056 mole) of 4-difluoro- methyl-4, 5-dihydro-l-(4-methyl-3-methoxyphenyl)-3- • methyl-1, 2, 4-triazol-5(1H)-one and 7.5 g (0.056 mole) of sulfuryl chloride in 100 mL of chloroform was stirred at room temperature for two hours. The reac¬ tion mixture was concentrated under reduced pressure to leave a residue. This residue was dissolved in methylene chloride and washed with an aqueous 10% sodium hydroxide solution. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 16.5 g of l-(2-chloro-4-methyl-5-methoxy- phenyl)-4-difluoromethyl-4, 5-dihydro-3-methyl-l,2,4- triazol-S(lH)-one as a solid. The nmr spectrum was consistent with the proposed structure. Step F l-(2-Chloro-4-methyl-5-hydroxyphenyl)- 4-di luoromethyl-4, 5-dihydro-3-methyl- 1,2, 4-triazol-5(lH)-one To a stirred solution of 16.0 g (0.053 mole) of l-(2-chloro-4-methyl-5-methoxyphenyl)-4-difluoro¬ methyl-4, 5-dihydro-3-raethyl-l,2,4-triazol-5(lH)-one in 100 mL of- methylene chloride at 10°C was added dropwise 39.6 g (0.16 mole) of boron tribromide. The resultant mixture was stirred at room temperature for two days. This mixture was washed with 100 L of water. The organic layer was dried with anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to leave an oil. This oil was stirred in petroleum ether:diethyl ether (90:10) forming a solid. The solid was collected by filtration to yield 10.5 g of l-(2-chloro-4-methyl-5- hydroxyphenyl)-4-di luoromethyl-4, 5-dihydro-3-meth l- l,2,4-triazol-5(lH)-one (mp 154-156°C). The nmr spectrum was consistent with the proposed structure. Step G Methyl 2-[4-chloro-5-(4-difluoromethyl- 4, 5-dihydro-3-methyl-5-oxo-1H-1,2,4- triazol-1-yl)-2-methylphenoxyJpropionate In a manner similar to Example 2, Step G, the reac¬ tion of 3.0 g (0.01 mole) of l-(2-chloro-4-methyl-5- hydroxyphenyl)-4-difluoromethyl-4, 5-dihydro-3-meth l- 1, 2, 4-triazol-5(lH)-one, 0.25 g (0.01 mole) of sodium hydride and 1.75 g (0.01 mole) of methyl 2-bromopro- pionate in 100 mL of N,N-dimethylformamide produced 3.7 g of methyl 2-[4-chloro-5-(4-difluoromethyl-4, 5- dihydro-3-methyl-5-oxo-lH-l,2,4-triazol-l-yl)-2- methylphenoxyJpropionate as an oil^ Compound 4. The nmr spectrum was consistent with the proposed structure. Compound 7 was prepared by the process described for Compound 4, but using ethyl 2-bromopropionate in Step G. Step H 2-[4-Chloro-5-(4-difluoromethyl-4, 5- dihydro-3-methyl-5-o o-lH-l ,2,4-triazol- - 1- j yl)-2-methylphenoxyJpropionic acid In a manner similar to Example 2, Step H, the reac¬ tion of 3.3 g (0.0088 mole) of methyl 2-[ 4-chloro-5- ( 4-difluoromethyl-4, 5-dihydro-3-methyl-5-oxo-lH-l , 2,4- triazol-1-yl) -2-methylphenoxyJpropionate with 1.5 g (0.27 mole) of potassium hydroxide in 50 mL of ethanol and 15 mL of water produced 2.7 g of 2-[4- chloro-5-( 4-di luoromethyl-4, 5-dihydro-3-methyl-5-oxo- lH-l,2,4-triazol-l-yl) -2-methyIphenoxyJpropionic acid as a solid (mp 56-60°C), Compound A3. The nmr spectrum was consistent with the proposed structure. Example 4 2-Nitropropyl 2-[ 2, 4-dichloro-5-( 4-difluoro- me hyl-4, 5-dihydro-3-methyl-5-oxo-lH-l ,2,4- riazol-l-yl)phenoxyJpropionate A stirred mixture of 0.5 g (0.0013 mole) of 2-1.2,4- dichloro-5-( 4-difluoromethyl-4, 5-dihydro-3-methyl-5- όxo-lH-1 , 2 , 4-triazol-l-yl)phenoxyJpropionic acid (Compound Al), 1.0 g (0.0095 mole) of 2-nitro-l- propanol and 0.05 g (0.0003 mole) of p-toluenesul- fonic acid monohydrate in 60 L of toluene was heated at reflux. The water generated in the reaction was removed by collection in a Dean-Stark trap. After refluxing for a total of two hours, the solvent was removed by distillation under reduced pressure leav¬ ing a residue. This residue was dissolved in diethyl ether and washed first with water then with an aqueous 10% sodium hydroxide solution. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to yield 0.5 g of 2-nitroprop.yl 2- [2, 4-dichloro-5-(4-difluoromethyl- 4, 5-dihydro-3-methyl-5-oxo-1H-1, 2,4-triazol-l-yl)- phenoxyJpropionate as an oil, Compound Bl. The nmr spectrum was consistent with the proposed structure. Compound 11 was also prepared by the method of Example 4 from Compound Al and n-butanol. Example 5 2-Propenyl 2-[2, 4-dichloro-5-( 4-difluoromethyl- 4, 5-dihydro-3-methyl-5-oxo-lH-l,2,4-triazol-l-yl) phenoxyJpropionate Under a dry nitrogen atmosphere,• a stirred solution of 0.5 g (0.0013 mole) of methyl 2-[2, 4-dichloro- 5-(4-difluoromethyl-4, 5-dihydro-3-methyl-5-oxo-lH- 1, 2, 4-triazol-l-yl)phenoxyJpropionate (Compound 2) and approximately 0.01 g of sodium methoxide in 30 mL of 2-propen-l-ol was heated at reflux. After approximately 5 mL of methanol was collected in a Dean-Stark trap, the reaction mixture was cooled slightly, and the remaining solvent removed by distillation under reduced pressure leaving a resi¬ due. This residue was dissolved in diethyl ether and washed with water. The organic phase was dried over anhydrous magnesium sulfate and filtered. The fil¬ trate was evaporated under reduced pressure to yield 0.55 g of 2-propenyl 2-[ 2, 4-dichloro-5-( 4-di luoro¬ methyl-4, 5-dihydro-3-methyl-5-oxo-lH-l, 2, 4-tria- zol-l-yl)phenoxyJpropionate as an oil, Compound B2. The nmr spectrum was consistent with the pro¬ posed structure. Analysis Calc'd for C 16 H 15 N 3 C1 2 F 2°4 : C 45 - 52 5 H 3 -58;N 9.95 • : Found: C 45.24;H 3.76;N 9.87 The following compounds were also prepared by the process of Example 5 from l-(2, 4-dichloro-5-hydroxy- phenyl)-4-difluromethyl-4,5-dihydro-3-methyl-l,2,4- triazol-5(lH)-one; compound Al; or compound A2 and the following reagents: Compound Reagent 9 n-propanol 10 2-propanol 15 n-propanol 16 - 2-propanol B3 2-propyn-l-ol B5 2-methoxyethanol Example 6. N-methylsulfonyl-2-[2, 4-Dichloro-5-(4-difluoro¬ methyl-4, 5-dihydro-3-me hyl-5-o.χo-lH-l,2,4- triazol-l-yl)phenoxyJpropionamide Step A 2-[2, 4-Dichloro-5-(4-difluromethyl-4,5- dihydro-3-methyl-5-oxo-lH-l,2,4-triazol- l-yl)phenoxyJ-propionyl chloride A stirred mixture of 2.9 g (0.0075 mole) of 2-[2,4-di- chloro-5-(4-difluoromethyl-4, 5-dihydro-3-methyl-5-oxo- 1H-1, 2, 4-triazol-l-yl)phenoxyJpropionic acid (Com¬ pound A-l) in 5 mL of thionyl chloride was heated at reflux for 1.5 hours. The mixture was cooled, and the excess thionyl chloride was removed by evaporation under reduced pressure, leaving 3.1 g of product as an oil. Step B N-Methylsulfonyl-2-[ 2, 4-dichloro-5-(4-di- fluoro-methyl-4,5-dihydro-3-methyl-5-oxo-lH- 1,2, 4-triazol-l-yl)phenoxyJpropionamide A mixture of 0.56 g of the oil from Step A and 0.56 g (0.0059 mole) of methanesulfonamide was heated at 80°C for 3.5 hours.- The mixture was cooled and diluted with water, forming a gummy precipitate. The water was decanted, and.the residue was partitioned between water and methylene chloride. The organic phase was washed with three 100 ml portions of water, dried over anhydrous magnesium sulfate, and filtered. The fil¬ trate was evaporated under reduced pressure to leave a tan solid which was dissolved in 30 mL of IN sodium hydroxide and 50 mL of water. The basic mixture was filtered, and the filtrate was made acidic with con¬ centrated hydrochloric acid. A precipitate formed and was collected by filtration. The filter cake was washed with water and dried to yield 0.34 g of N-meth- ylsulfonyl-2-[2, 4-dichloro-5-(4-difluoromethyl-4, 5-di- hydro-3-methyl-5-oxo-lH-l; 2, 4rtriazol-l-yl)phenoxyJpro¬ pionamide (mp 185-188°C), Compound C3. The nmr spectrum was consistent with the proposed structure. Analysis Calc'd for C 14 H 14 C1 2 F-N 4 0 5 S: C 36.61; H 3.07; N 12.20 Found: C 36.79; H 3.01; N 12.41 Compounds C4, C5 and C6 were prepared by the pro¬ cess described in Example 6 using trifluoromethanesul- fonamide, ammonia and methylamine respectively in Step B. Compounds C2 and C18 were prepared by the method of Example 6 from Compound A2, using methylamine and methanesulfonamide respectively in Step B. Example 7 Ethyl 2-[2, 4-dibromo-5-(4-di luoromethyl-4, 5- dihydro-3-methyl-5-oxo-lH-l,2, 4-tria∑ol-l-yl)- phenoxyJpropionate Step A l-(2, 4-Dibromo-5-methoxyphenyl)-4-difluoro- methyl-4,5-dihydro-3-methyl-l,2,4-triazol- .5(_lH)-one To a stirred mixture of 12.0 g (0.047 mole) of l-(3- methoxyphenyl)-4-difluoromethyl-4, 5-dihy.dro-3-methyl- 1,2, 4-triazol-5(lH)-one (prepared from 3-methoxy- aniline using the method of Example 2, Steps B-E) in 75 mL of acetic acid was added 30.0 g (0.19 mole) of bromine. The mixture was heated at reflux for six hours, then cooled. The solvent was removed by dis¬ tillation, leaving a residue. This residue was dis¬ solved in diethyl ether, 'and the resultant solution was washed first with an aqueous 10% sodium thiosul- fate solution followed by water. The organic solution was dried over anhydrous magnesium sulfate and fil¬ tered. The filtrate was evaporated under reduced pressure, leaving a solid. This solid was triturated in petroleum ether and filtered to yield 17.4 g of l-(2, 4-dibromo-5-methoxyphenyl)-4-di luoromethyl-4, 5- dihydro-3-methyl-l,2, 4-triazol-5(lH)-one. The nmr spectrum was consistent with the proposed structure. Step B l-(2, 4-Dibromo-5-hydroxyphenyl)-4-di luoro¬ methyl-4, 5-dihydro-3-methyl-1,2,4-triazol- 5(lH)-one A mixture of 17.2 g (0.042 mole) of l-(2, 4-dibromo- 5-methoxyphenyl)-4-di luoromethyl-4, 5-dihydro-3-methyl- 1, 2, 4-triazol-5-(lH)-one and 50.6 g (0,020 mole) of boron tribromide in 100 mL of methylene chloride was stirred at room temperature for 18 hours. The mixture was washed with 50 mL of water, and the organic phase was dried over anhydrous magnesium sulfate. This mix- ture was filtered, and the filtrate was evaporated under reduced pressure to yield 16.1 g of l-(2,4-di- bromo-5-hydrox*yphe"nyl)-4-difluoromethyl-4, 5-dihydro-3- methyl-1,2, 4-triazol-5-(lH)-one as a solid. The nmr spectrum was consistent with the proposed structure. Step C Ethyl 2-[2, 4-dibromo-5-(4-difluoromethyl- 4,5-dihydro-3-methyl-5-oxo-1H-1, 2, 4-triazol' 1-yl) -phenoxyJpropionate To a stirred solution of 1.25 g (0.0031 mole) of l-(2, 4-dibromo-5-hydroxyphenyl)-4-difluoromethyl-4, 5- dihydro-3-methyl-l,2, 4-triazol-5(lH)-one in 60 mL of N,N-dimethylformamide was added 0.57 g (0.0033 mole) of ethyl 2-bromopropionate. The resultant mixture was heated at 130°C for two hours, then was cooled. The solvent was evaporated from the mixture under reduced pressure, leaving a solid. This solid was dissolved in diethyl ether, and the solution was washed first with water, then with an aqueous 10% sodium hydroxide solution. The organic solution was dried over anhy¬ drous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 1.0 g of ethyl 2-[2, 4-dibromo-5-(4-difluoromethyl-4, 5-di- hydro-3-methyl-5-oxo-lH-l, 2, 4-triazol-1-yl)phenoxy] propionate as an oil, Compound 8. The nmr spectrum- was consistent with the proposed structure. Example 8 1-Methylpropyl 2-[2, 4-dichloro-5-(4-difluoro- methyl-4, 5-dihydro-3-methyl-5-oxo-lH-l,2,4- triazol-1-yl)phenoxyJpropionate To a stirred solution of 1.0 g (0.0025 mole) of 2-[2, 4-dichloro-5-(4-difluoromethyl--4, 5-dihydro-3- methyl-5-oxo.-1H-1 2, 4-1riazol1-yl)phenoxyJpropionyl chloride (prepared in Example 6, Step A) in 15 mL of sec-butanol was added 0.27 g (0.0027 mole) of tri- ethyla ine. The reaction mixture was stirred at room temperature for 20 minutes, then heated at 70°C for 1-1/2 hours. The mixture was allowed to cool and was stirred at room temperature for approximately 18 hours. The solvent was removed by evaporation under reduced pressure, leaving a residue which was parti¬ tioned between deithyl ether and water. The organic phase was washed in succession with water, an aqueous 10% sodium hydroxide solution, water, aqueous 10% hydrochloric acid, a saturated aqueous sodium bicar¬ bonate solution, and water. The organic phase was dried" over anhydrous magnesium sulfate, then fil- . tered. The filtrate was evaporated under reduced pressure to yield 0.42 g of 1-methylpropyl 2-[2, 4- dichloro-5-( 4-difluoromethyl-4, 5-dihydro-3-methyl-5-oxo- 1H-1,2, 4-triazol-l-yl)-phenoxyJpropionate as an oil, Compound 12. The nmr spectrum was consistent with the proposed structure. Compound B4 was also prepared by the method of Example 8 from the acid chloride of Compound A2 and 2-propyn-l-ol. Example 9 Ethyl [2, 4-dichloro-5-(4-difluoromethyl-4,5- dihydro-3-methyl-5-oxo-lH-l,2,4-triazol-l-yl)- phenoxy]fluoroacetate To a stirred mixture of 2.0 g (0.0065 mole) of l-(2,4- dichloro-5-hydroxyphenyl)-4-difluoromethyl-4, 5-dihydro- 3-methyl-l, 2, 4-triazol-5(lH)-one and 0.91 g (0.0065 mole) of ethyl chloro luoroacetate in 50 mL of ethanol was added a . ' solution of 0.15 g (0.0065 mole) of sodium in 5 mL of ethanol. The reaction mixture was heated at reflux for 34 hours. The mixture was cooled, and the solvent was removed by evaporation under reduced pressure, leaving a residue. This residue was dis¬ solved in diethyl ether, "and the solution was washed first with water, followed by an aqueous 10% sodium hydroxide solution. The organic phase was dried over anhydrous magnesium sulfate, then filtered. The fil¬ trate was evaporated under reduced pressure to yield 0.95 g of ethyl [2, 4-dichloro-5-(4-difluoromethyl-4, 5- dihydro-3-methyl-5-oxo-lH-l, 2, 4-triazol-1-yl)phenoxyJ- fluroacetate as an oil, Compound 51. The nmr spectrum was consistent with the proposed structure. Example 10 Ethyl 2-[2, 4-dichloro-5-(4-fluoromethyl-4, 5- dihydro-3-methyl-5-oxo-lH-l,2, 4-triazol-l-yl)- phenoxyJpropionate Step A l-[2, 4-Dichloro-5-(l-methylethoxy)phenylJ-4- fluoromethyl-4, 5-dihydro-3-methyl-1,2,4- triazol-5(lH)-one A solution of 6.0 g (0.020 mole) of 1-[2, 4-dichloro- 5-(l-methylethoxy)phenyl J-4,5-dihydro-3-methyl-1, 2,4- triazol-5(lH)-one in 45 mL of N,N-dimethylformamide was added to O.SS g (0.022 mole) of sodium hydride i 30 mL of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 15 minutes. Chloro luoromethane was added dropwise to the stirred reaction mixture by condensing the gas on a dry ice condenser. Du'ring the addition the mixture was heated slowly to 60°G at which point the mixture began to reflux. The addition of chlorofluromethane was dis¬ continued, and the reaction mixture was allowed to cool to room temperature and stand for approximately 18 hours. Heating at reflux was resumed, and an addi¬ tional amount of chlorofluoromethane was added during a ten minute period. After complete addition, the reaction mixture was heated at reflux for one hour, then allowed to cool. The solvent was removed by dis¬ tillation under reduced pressure, leaving a residue. This residue was partitioned between diethyl ether and water. The organic phase was washed first with IN sodium hydroxide, then water. The organic solution was dried over anhydrous magnesium sulfate- and filtered. The filtrate was evaporated under reduced pressure to yield 3.8 g of 1- [ 2, 4-dichloro-5-(l- methylethoxy)phenyl J-4-fluoromethyl- 4, 5-dihydro-3- methyl-1 , 2, 4-triazol-5(lH) -one as an oil. The nmr spectrum was consistent with the proposed structure. Step B l-(2, 4-Dichloro-5-hydroxyphenyl) -4-fluoro¬ methyl-4, 5-dihydro-3-methyl-l ,2,4-triazol- 5(lH)-one To 5mL of stirring concentrated sulfuric acid was added portionwise 0.53 g (0.0016 mole) of l-[2,4-di- chloro-5-(l-methylethoxy)phenyl J-4-f.luoromethyl-4, 5- dihydro-3-methyl-l ,2,4-triazol-5(lH)-one. After complete addition, the mixture was stirred at room temperature for 2.5 hours. The mixture was poured into 100 mL of ice water and stirred for 30 minutes. The aqueous mixture was extracted with diethyl ether, and the extract was washed with water. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 0.34 g of l-(2, 4-dichloro-5-hydroxy- phenyl)-4-fluoromethyl-4,5-dihydro-3-methyl-l,2, 4- triazol-5(lH)-one as a solid. The nmr spectrum was consistent with the proposed structure. This, reaction was repeated using 2.8 g of l-[2,4- dichloro-5-(l-methylethoxyJ-4-fluororaethyl-4, 5-dihydro- 3-methyl-l, 2, 4-triazol-5(lH)-one, producing an addi¬ tional 1.9 g of product. Step C Ethyl 2-[2, 4-dichloro-S-(4-fluoromethyl- 4, 5-dihydro-3-methyl-5-oxo-1H-1, 2, 4-tria¬ zol-1-yl)-phenoxyJpropionate A mixture of 0.56 g (0.0019 mole) of l-(2, 4-dichloro- 5-hydroxyphenyl)-4-fluoromethyl-4,5-dihydro-3-methyl- 1,2, 4-triazol-5(lH)-one and 1.1 g (0.0076 mole) of anhydrous potassium carbonate in 15 mL of acetone was stirred for 15 minutes. Sodium iodide (approximately 0.01 g) and 0.37 g (0.002 mole) of ethyl 2-bromo- propionate were added, and the resultant mixture was heated at reflux for 1.5 hours. The mixture was cooled and filtered. The filtrate was evaporated under reduced pressure, leaving a residue. This resi¬ due was partitioned between diethyl ether and water. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and filtered. The fil¬ trate was evaporated under reduced pressure, leaving an oil. This oil was stirred in n-pentane, and the supernant was decanted, leaving an oily residue. The oil was dried at 70°C under a stream of nitrogen to yield 0.70 g of ethyl 2-[2, 4-dichloro-5-(4-fluoro¬ methyl-4,5-dihydro-3-methyl-5-oxo-lH-l,2,4-triazol-l- yDphenoxyJpropionate, Compound 13. The nmr* spectrum was consistent with the proposed structure. Example 11 N-( 4-Methylphenylsulfonyl)-2-[2-chloro-4-fluoro-5- (4-difluoromethyl-4, 5-dihydro-3-methyl-5-oxo-lH-l, 2, 4-triazol-1-yl)phenoxyJpropionamide A stirred mixture of 0.78'g (0.0021 mole) of 2-[2- chloro-4-fluoro-5-(4-diflubromethyl-4, 5-dihydro-3- methyl-5-oxo-lH-l, 2, 4-triazol-1-yl)phenoxyJpropionic acid, 0.42 g (0.0021 mole) of p-toluenesulfonyl iso- cyanate and 0.05 g (0.0004 mole) of 4-dimethylamino- pyridine in 50 mL of toluene was heated at reflux for approximately 18 hours. The mixture was allowed to cool to room temperature and was stirred for 24 hours. The solvent was removed by evaporation at reduced pressure to leave a residue. This residue was purified by column chromatography on silica gel, elut- ing with toluene :ethyl acetate (1:1). The appropriate fractions were combined and evaporated under reduced pressure to yield 0.7 g of N-(4-methylphenylsulfonyl)- 2-[2-chloro-4-fluoro-5-(4-difluoromethyl-4, 5-dihydro-3- methyl-5-oxo-lH-l,2, 4-triazol-1-yl)phenoxyJpropionamide as a solid, Compound CIO. The nmr spectrum was consistent with the proposed structure. Compound C25 was prepared by the method of Example 11 using 2-chlorobenzenesulfonyl isocyanate. Examp le 12 2-[2-Chloro-4-fluoro-5-(4-difluoromethyl-4,5- dihydro-3-methyl-5-oxo-1H-l,2,4-triazol-l-yl) phenoxyJpropionic acid, sodium salt. A mixture of 1.0 g (0.0027 mole) of 2-[2-chloro-4- fluoro-5-( 4-difluoromethyl-4, 5-dihydro-3-methyl-5- oxo-lH-1,2, 4-triazol-l-yl)phenoxyJpropionic acid and 0.07 g (0.0027 mole) of sodium hydride in 30 mL of tetrahydrofuran was stirred at room temperature for approximately 18 hours. The solvent was removed by evaporation to yield 0.9 g of 2-[2-chloro-4-fluoro-5- ( 4-difluoromethyl-4, 5-dihydro-3-methyl-5-oxo-lH-l, 2,4- triazol-1-yl) phenoxyJpropionic acid, sodium salt as a solid, Compound A4. • Compounds C19 and C20 were prepared by the method of Example 12 from compounds C18 and CIO respective¬ ly. Compound A6 was prepared by a method analogous to that of Example 12 from Compound A2, substituting iso- propylamine for sodium hydride. Example 13 [2, 4-Dichloro-5-(3-difluoromethyl-4, 5-dihydro- 4-methyl-5-oxo-lH-l,2, 4-triazol-1-yl)phenoxy]- acetamide Step A Ethyl difluoroacetylcarbamate During a 30 minute period 65.4 g (0.55 mole) of thionyl chloride was added to 50.0 g (0.52 mole) of difluoroacetic acid while stirring. Gas evolved dur¬ ing the addition was returned to the reaction mixture by condensation on a dry ice condenser. After com- plete addition, the mixture was stirred at room tem¬ perature for approximately two hours. Urethane, 46.4 g (0.52 mole),^ was added and, after complete addition, the reaction, mixture was heated at 60-70°C for three hours. The mixture was cooled to room temperature and stirred for approximately 18 hours. The mixture was again heated at about 75°C for two hours, then cooled. The mixture was evaporated under reduced pressure to leave an oily residue. This residue crystallized upon standing. The crystallized residue was washed with petroleum ether and filtered to yield 68.4 g of ethyl di luoroacetylcarbamate (mp 55-57°C). Step B 1-[2, 4-Dichloro-5-(l-methylethoxy)phenyl ]- 3-difluoromethyl-4, 5-dihydro-1,2,4-triazol- 5(lH)-one To a stirred solution of 11.8 g (0.05 mole) of 2,4-di- chloro-5-(l-methylethoxy)phenylhydrazine and 10.0 g (0.06 mole) of ethyl difluoroacetylcarbamate in 130 mL of xylene was added 2.5 g (0.02 mole) of phosphorus pentoxide. After complete addition the mixture was heated at reflux for 1.5 hours then allowed to cool to room temperature for approximately 18 hours. The reaction mixture was decanted from a dark residue in the reaction flask and washed with water. The washed mixture was extracted with a 10% aqueous sodium hydroxide solution. The basic extract was made acidic with concentrated hydrochloric acid to form an oily precipitate. This aqueous phase was decanted from the oily residue and fresh water added to wash the resi¬ due. This residue was dissolved in 160 mL of methyl¬ ene chloride and filtered through a celite pad. The filtrate was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to leave a semi-solid residue. The residue was triturated with approximately 125 mL of petroleum ethe;r to ' provide 8.2 g of l-[2, 4-dichloro- 5-(l-raethylethoxy)phenylJ-3-difluoromethyl-4, 5-dihydro- 1,2, 4-triazol-5(lH)-one. Step C l-[ 2, 4-Dichloro-5-(l-methylethoxy)phenylJ- 3-difluororaethyl-4,5-dihydro-4-methy1-1,2,4- triazol-5(lH)-one. A stirred mixture of 4.0 g (0.012 mole) of l-[2,4-di- chloro-5-(1-methylethoxy)phenylJ-3-difluoromethyl-4, 5- dihydro-1,2, 4-triazol-5(lH)-one and 4.1 g (0.03 mole) of potassium carbonate in 160 mL of acetone was heated at reflux for 0.5 hours then cooled to about 50°C. Methyl iodide, 8.4 g (0.06 mole), was added and the mixture stirred at 45° for one hour then at reflux for one hour. The mixture was cooled to room temperature and evaporated under reduced pressure to leave an oil. This oil was partitioned between methylene chloride and water. The organic phase was washed with a 10% aqueous sodium hydroxide solution and then dried over anhydrous magnesium sulfate. The mixture was filtered and the filtrate evaporated under reduced pressure to leave an oil. This oil solidified when stirred with petroleum ether and upon filtration pro¬ vided 2.6 g of l-[2, 4-dichloro-5-(l-methylethoxy)- phenylJ-3-difluoromethyl-4, 5-dihydro-4-methyl-1,2,4- triazol-5-(lH)-one (mp 95-97°C). Step D l-(2, 4-Dichloro-5-hydroxyphenyl)-3-difluoro- methyl-4, 5-dihydro-4-methyl-l,2,4-triazol- 5(lH)-one Hydrolysis of 2.2 g (0.0063 mole) of 1-[2, 4-dichloro- 5-(1-methylethoxy)phenylJ-3-difluoromethy1-4, 5-dihydro- 4-methyl-l, 2, 4-triazol-5(lH)-one in 5 mL of concen¬ trated sulf.uri,c acid produced 1.4 g of l-(2,4-di- chloro-5-hydroxyphenyl)-3-difluoromethyl-4,5-dihydro- 4-methyl-l,2,4-triazol-5(lH)-one (mp 176-179°C). Step E [2, 4-Dichloro-5-(3-difluoromethyl-4,5- dihydro-4-methyl-5-o o-lH-l,2,4-triazol-l- yl)phenoxyJacetamide In a manner similar to Example 1, the reaction of 0.72 g (0.00023 mole) of l-(2, 4-dichloro-5-hydroxyphenyl)- 3-difluromethyl-4, 5-dihydro-4-methyl-l,2,4-triazol- 5(lH)-one, 0.32 g (0.00023 mole) of potassium carbon¬ ate, and 0.47 g (0.00025 mole) of iodoacetamide in 5 mL of acetone produced 0.69 g of [2, 4-dichloro-5-(3- di luoromethyl-4, 5-di ydro-4-methyl-5-oxo-lH-l, 2., 4- triazol-l-yl)phenoxyJacetamide (mp 190-193.5°C). The nmr spectrum was consistent with the proposed structure. The following compounds were prepared by the pro¬ cess of S. Chandrasekaran et al., Synthetic Communica¬ tions, 12(9), 727-731 (1982) from Compound A2 and the following reagents. Compound Reagent B8 tetrahydrofurfuryl alcohol B9 methyl hydroxyacetate B10 2-methyl-3,3,4, 4-tetra luoro-2-butanol B12 furfuryl alcohol B13 N,N-dimethylethanolamine B14 3-hydroxytetrahydro uran B15 phenol B17 ethanethiol B18 ethyl 2-mercaptoacetate B30 trifluoroethanol B31 acetone cyanohydrin. B32 benzyl alcohol B33 2-propanethiol Cll 0,N-dimethylhydroxylamine hydrochloride Compound Reagent C12 (2-propynyl)amine C13 aniline C1.4 dimethylamine C15 diethylamine C16 ■ ethylamine hydrochloride C17 glycine methyl ester hydrochloride C22 2-amino-2-methylpropionitrile C23 N-methylaniline Compound B25 was prepared by the method of Lonord et al. , J. Org. Chem. ,27., 282-284 (1962) from Compound B23. Compound A5 was prepared by the hydrolysis of Compound 22 using the procedure described by Kurtev et al. , Synthesis (1975), 106-108. Characterizing properties of some of the com¬ pounds of the invention are given in Table 6 below. Example 14 N-( 2, 5-dimethoxyphenylsulfonyl) -2- [ 2-chloro-4- fluoro-5-( 4-difluoromethyl-4, 5-dihydro-3-meth l- 5-oxo-lH-1,2, -triazol-1-yl)phenoxyJpropionamide Step A 2, 5-Dimethoxyphenylsulfonamide To a stirred solution of 15.0 g (0.063 mole) of 2, 5-dimethoxybenzenesulfonyl chloride in 150 mL of tetrahydro uran was added dropwise 80 mL of ammonia (28% aqueous solution). After complete addition the mixture was allowed to stir for 1.75 hours at room temperature. Upon standing the mixture separated into two phases. The organic phase was removed from the aqueous phase and was evaporated under reduced pres¬ sure to leave a solid residue. This residue was recrystallized from hot water (125 mL) and ethanol (40 mL) to yield 13.1 g of 2, 5-dimethoxyphenylsul on¬ amide (mp 146.5-148.5). The nmr spectrum was consistent with the proposed structure. Step B- N-( , 5-Dimethoxyphenylsulfonyl) -2-bromo- propionamide A stirred mixture of 7.0 g (0.032 mole) of 2,5-dimeth- oxyphenylsulfonamide in 10 mL of 2-bromopropionyl chloride was heated at reflux for 40 minutes then allowed to cool to room temperature. The resultant solution was poured into petroleum ether. Crystals formed after scratching the sides of the flask and were collected by filtration. The filter cake was washed four times with fresh petroleum ether to yield 10.3 g of N-( 2, 5.-dimethoxyphenylsulfonyl) -2-bromo- propionamide (mp 116-118°C). The nmr spectrum was consistent with the proposed structure. Step C N-( 2.5-Dimethoxyphenylsulfonyl) -2-[ 2- chloro-4- luoro-5-( 4-di luorometh l-4,5- dihydro-3-methyl-5-oxo-lH-l ,2,4-tria∑ol- 1-yl)phenox Jpro ionamide To a stirred solution of 0.75 g (0.0026 mole) of l-( 4-chloro-2-fluoro-5-hydroxyphenyl)-4-difluoro- methyl-4, 5-dihydro-3-methyl-l ,2,4-triazol-5(lH) -one and 0.89 g (0.0026 mole) of N-( 2, 5-dimethoxyphenyl- sulfonyl) -2-bromopropionamide in 50 mL of acetone was added 1.04 g (0.0026 mole) of potassium -carbonate. Afte'r complete addition the mixture was heated at 45°C for two days. The resultant mixture was cooled and the solvent was removed by evaporation under reduced pressure to leave a residue. This residue was dis¬ solved in 100 mL of water. The aqueous solution . was acidified by the dropwise addition of concentrated hydrochloric acid producing a precipitate. The preci¬ pitate was collected by filtration. The filter cake was washed with water and then dried under reduced pressure to leave 1.23 g of N-(2, 5-dimethoxyphenylsul- onyl)-2-[2-chloro-4-fluoro-5-(4-di luoromethyl-4, 5- di ydro-3-methyl-5-oxo-lH-l,2, 4-triazol-1-yl)phenoxyJ- propionamide (mp 168-172°C) Compound C90. The nmr spectrum was consistent with the proposed structure. Example 15 l-(4-Chloro-2-fluoro-5-methoxyphenyl)-4, 5- dihydro-3-methyl-l, 2, 4-triazol-5(lH)-one as an intermediate Step A N' -(4-Chloro-2-fluoro-5-methoxyphenyl)- acetamidrazone A stirred mixture of 1.91 g (0.01 mole) of 4-chloro- 2-fluoro-5-methoxyphenylhydrazine and 1.97 g (0.01 mole) of 3-(l-iminoethylmercapto)-1-propanesulfonic acid, inner salt, (prepared by the method of Reid et al, Ann. Chem. 676, 114 (1964)) in 50 mL of anhydrous ethanol was heated at reflux for 1.25 hours. The mix¬ ture was cooled and evaporated under reduced pressure to leave 3.96 g of a residue. A portion of this resi¬ due, 3.33 g, was dissolved in 50 mL of water. The resultant cloudy solution was filtered through a pad of celite and the filtrate was extracted with meth¬ ylene chloride. The clarified aqueous solution was basified with approximately 8 mL of an aqueous 10% sodium hydroxide solution. An oil precipitated from the basic mixture and slowly solidified. This solid was collected by filtration. The filter cake was washed with water to yield 1.31 g of N' -( 4-chloro-2- fluoro-5-methoxyphenyl)acetamidrazone (mp 106-107°C). The nmr analysis was consistent with the proposed structure. Analysis calc'd for C g H 11 ClFN 3 0: C 46.66, H 4.79, N 18.14 . Found: C 46.10, H 4.81, N 17.70 Step B l-( 4-Chloro-2- luoro-5-methoxyphenyl) - 4, 5-dihydro-3-methyl-l, 2,4-triazol- 5(lH)-one A solution of 1.71 g (0.0086 mole) of trichloromethyl chloroformate in 5 L of toluene was added dropwise to a stirred solution of 1.0 g (0.0043 mole) of N'-(4- chloro-2- luoro-5-methoxyphenyl)acetamidrazone in 50 L of toluene. After complete addition the mixture was stirred at room temperature for five minutes then was heated slowly until a slow reflux was obtained. Reflux was maintained for approximately 15 minutes. The mixture was cooled and evaporated under reduced pressure to leave 1.22 g of a solid. Approximately 1.0 g of this solid was dissolved in 100 mL of methylene chloride. The resultant solution was fil¬ tered and the filtrate was extracted with three 25 mL portions of an aqueous 10% sodium hydroxide solution followed by three 25 mL portions of IN sodium hydroxide. Each set of three similar extracts were combined and washed with methylene chloride. Both of the washed extracts were acidified with concentrated hydrochloric acid producing a precipitate from each. The solids were collected by filtration to provide 0.3 g and 0.12 g, from the 10% and IN base solutions respectively, of l-( 4-chloro-2- luoro-5-methoxy- phenyl)-4, 5-dihydro-3-methyl-1,2, 4-triazol-5(lH)-one (mp 209-211°C). The nmr spectrum was consistent with the proposed structure. Example 16 l-(2, 4-Dichloro-5-hydroxyphenyl)-3-chloro- difluorome hyl- , 5-dihydro-4-methyl-l, 2,4- triazol-5(lH)-one as an intermediate Step A N' -[2, 4-Dichloro-5-(l-methylethoxy)phenylJ- chlorodifluoroacetarn drazone A stirred solution of 9.4 g (0.04 mole) of 2,4-di- chloro-5-(l-methylethoxy)phenylhydrazine in 350 mL of absolute methanol was cooled to 0°. Gaseous chlorodi- fluoroacetonitrile (8.0 g, 0.07 mole) was added to the mixture. After complete addition the mixture was allowed to warm to room temperature and stir for 3.5 hours. The stirring was stopped and the mixture stood at room temperature for two days. The solvent was evaporated from the mixture under reduced pressure to leave 13.86 g of N' -[2, 4-dichloro-5-(l-methyleth- oxy)phenylJchlorodi luoroacetamidrazone as an oily residue. Step B l-[2, 4-Dichloro-5-(l-methylethoxy)phenylJ- 3-chlorodifluoromethyl-4, 5-dihydro-l,2,4- triazol-5(1H)-one In a manner similar to Example 15, Step B, the reac¬ tion of 13.86 ι of the oily residue from Step A plus 2.7 g of similar material prepared in a separate experiment and 19.87 g (0.1 mole) of trichloromethyl chloroformate in 600 mL of toluene produced 5.4 g of l-[2, 4-dichloro-5-(l-methylethoxy)phenyl J-3-chlorodi- fluoromethyl-4, 5-dihydro-1, 2, 4-triazol-5(lH)-one (mp 115-119°C). ' : The nmr spectrum was consistent with the proposed structure. Step C l-[ 2, 4-Dichloro-5-(l-methylethoxy)phenylJ- 3-chlorodifluoromethyl-4, 5-dihydro-4-methyl* 1,2, 4-triazol-5(lH)-one In a manner similar to Example 13, Step C, the reaction of 4.0 g (0.011 'mole) of 1-[2, 4-dichloro-5- (1-methylethoxy)phenyl]-3- ' chlorodifluoromethyl-4, 5-di- hydro-1, 2, 4-triazol-5(1H)-one, 4.26 g (0.03 mole) of methyl iodide, and 2.07 g (0.015 mole) of potassium carbonate in 40 mL of acetone provided 3.74 g of l-[2, 4-dichloro-5-(1-methylethoxy)phenylJ-3-chlorodi- fluoromethyl-4, 5-dihydro-4-me hyl-l, 2, 4-triazol-5(lH)- one as a solid. Recrystallization of a small portion of this solid from ethanol and water provided a pale yellow solid, mp 69-72°C. The nmr spectrum was consistent with the proposed structure. Analysis calc'd for C 13 H 12 C1 3 F 2 N 3°2 : C 40, 39 > H 3 - 13 > N 10 - 87 Found: C 40.92, H 3.28, N 10.96. Step D l-(2, 4-Dichloro-5-hydroxyphenyl)-3- chlorodi luoromethyl-4, 5-dihydro-4- methy1-1,2, 4-triazol-5(lH)-one Hydrolysis of 2.6 g (0.0067 mole) of 1-[2, 4-dichloro- 5-(1-meth lethoxy)phenyl ]-3-chlorodifluoromethyl-4, 5- dihydro-4-methyl-l, 2, 4-triazol-5(lH)-one in 10 mL of concentrated sulfuric acid produced 2.17 g of l-(2,4- dichloro-5-hydroxyphenyl)-3-chlorodifluoromethyl-4, 5- dihydro-4-me.tliyl-l,2, 4-triazol-5(lH)-one as a solid (mp 146-148° ' C). The nmr spectrum was consistent with the proposed structure. Analysis calc'd for C 1() H 6 C1 3 F 2 N 3 0 2 : C 34.86, H 1.76, N 12.20 Found: C 35.30, H 1.59, N 12.25 HERBICIDAL ACTIVITY The plant test species used in demonstrating the herbicidal activity of compounds of this invention include cotton (Gossypium hirsutum var. Stoneville), soybean (Glycine max var. Williams), field corn (Zea mays var. Agway 595S), wheat (Triticum aestivium var. Prodax) , rice (Oryza sativa), field bindweed (Convol¬ vulus arvensis) , morningglory (Ipomea lacunosa or Ipomea hederacea, velvetleaf (Abutilon theophrasti) , barnyardgrass (Echinochloa crus galli) , green foxtail (Setaria viridis) , and johnsongrass (Sorghum hale- pense) , yellow nutsedge (Cyperus esculentus) . Seeds or tubers of the plant test species were planted in furrows in steam sterilized sandy loam soil contained in disposable fiber flats. A topping soil of equal portions of sand and sandy loam soil was placed uniformly on top of each flat to a depth of approximately 0.5 cm. The flats for the preemergence test were watered, then drenched with the appropriate amount of a solu¬ tion of the test compound in a mixture of acetone and water containing a small amount (up to 0.5% v/v) of sorbitan monolaurate e ulsi ier/solubilizer. The - concentration of the test compound in solution was varied to give a range of application rates, generally 8.0 kg/ha and submultiples thereof. The flats were placed in a greenhouse and watered regularly at the soil surface ' or 21 days at which time phytotoxicity data were recorded.. The flats for the postemergence test were placed in a greenhouse and watered for 8-10 days, then the foilage of the emerged test plants was sprayed with a solution of the test compound in acetone-water con¬ taining up to 0.5% sorbitan monolaurate. After spray¬ ing, the foilage was kept dry for 24 hours, then watered regularly for 21 days, and phytotoxicity data recorded. Phytotoxicity data were taken either as percent kill or percent control. Percent control was deter¬ mined by a method similar to the 0 to 100 rating system disclosed in "Research Methods in Weed Science," 2nd ed. ,. B. Truelove,* Ed. ; Southern'Weed Science Society; Auburn University, Auburn, Alabama, 1977. The present rating system is as follows: Herbicide Rating System Rating Description Percent of Main ' Crop Weed Control Categories Description Description 0 No effect No crop No weed reduction control or injury 10 Slight dis- Very poor weed coloration control or stunting 20 Slight Some dis- Poor weed effect coloration, control stunting or stand loss 30 Crop injury Poor to defi- ore pronounced cient weed but not lasting control 40 Moderate injury, Deficient weed crop usually, control recovers 50 Moderate Crop injury Deficient to e fect more lasting, moderate weed recovery control 60 Lasting crop Moderate weed injury no control recovery 70 Heavy injury and Control some¬ stand loss what less than satisfactory 80 Severe Crop nearly des¬ Satisfactory troyed a few to good weed survivors control • 90 Only occasional Very good to live plants left excellent control 100 Complete Complete crop Complete weed effect destruction destruction Herbicidal data at selected application rates are given for various compounds of the invention in the tables below. The test compounds are identified in the tables of -herbicidal data below by numbers which correspond to those used above. In the Tables of herbicidal data below: "kg/ha" is kilograms per hectare, "% K" is percent kill, and "% C" is percent control. For herbicidal application, the active compounds as above defined are formulated into herbicidal com¬ positions by admixture in herbicidally effective amounts with adjuvants and carriers normally employed in the art for facilitating the dispersion of active ingredients for the particular utility desired, recog¬ nizing the fact that the formulation and mode of application of a toxicant may affect the activity of the material in a given application. Thus, for agricultural use the present herbicidal compounds may be formulated as granules of relatively large particle size, water-soluble or water-dispersible granules, as powdery dusts, as wettable powders, as emulsifiable concentrates, as solutions or as any of several other known types of formulations, depending on the desired mode of application. For preemergence application these herbicidal compositions are usually applied either as sprays, dusts, or granules to the areas in which suppression of vegetation is desired. For postemergence control of established plant growth, sprays or dusts are most commonly used. These formulations may contain as little as 0.5% to as much as 95% or more by weight of active ingredient. Dusts are free flowing admixtures of the active ingredient with finely divided solids such as talc, natural clays, kieselguhr, flours such as walnut shell and cottonseed flours, and other organic and inorganic solids which* att as dispersants and carriers for the toxicant; these finely divided solids have an average particle size of less than about 50 microns. A typi¬ cal dust formulation useful herein is one containing 1.0 part of the herbicidal compound and 99.0 parts of talc. Wettable powders, also useful formulations- for both pre- and postemergence herbicides, are in the form of finely divided particles which disperse readily in water or other dispersant. The wettable powder is ultimately applied to the soil either as a dry dust or as an emulsion in water or other liquid. Typical carriers for wettable powders include Fuller's earth, kaolin clays, silicas, and other highly absor¬ bent, readily wet inorganic diluents. Wettable pow¬ ders normally are prepared to contain about 5-80% of active ingredient, depending on the absorbency of the carrier, and usually also contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion. For example, a useful wettable powder formulation contains 80.8 parts of the herbicidal compound, 17.9 parts of Palmetto clay, and 1.0 part of sodium lignosulfonate and 0.3 part of sulfonated aliphatic polyester as wetting agents. Frequently, additional wetting agent and/or oil will be added to the tank-mix for postemergence application to facili¬ tate dispersion on the foliage and absorption by the plant. Other useful formulations for herbicidal applica¬ tions are e ulsifiable concentrates. Emulsifiable concentrates are homogeneous liquid or paste composi¬ tions dispersible in water or other dispersant, and may consist entirely of the herbicidal compound and a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy. aromatic naphthas, isophorone, or other non-volatile organic solvent. For • herbicidal application these concen¬ trates are dispersed in water or other liquid carrier, and normally applied as a spray to the area to be treated. The percentage by weight of the essential active ingredient may vary according to the manner in which the composition is to be applied, but in general comprises 0.5 to 95% of active ingredient by weight of the herbicidal composition. Typical wetting, dispersing or emulsifying agents used in agricultural formulations include, for exam¬ ple, the alkyl and alkylaryl sulfonates and sulfates and their sodium salts; polyhydric alcohols; and other types of surface active agents, many of which are available in commerce. The surface active agent, when used, normally comprises 1% to 15% by weight of the herbicidal composition. Other useful formulations for herbicidal applica¬ tions include simple solutions of the active ingre¬ dient in a dispersant in which it is completely solu¬ ble at the desired concentration, such as acetone, alkylated naphthalenes, xylene or other organic sol¬ vents. Granular ormulations, wherein the toxicant is carried on relatively coarse particles, are of parti¬ cular utility for aerial distribution or for penetra¬ tion of cover crop canopy. Pressurized sprays, typically aerosols wherein.the active ingredient is dispersed in finely divided form as a result of vapor¬ ization of a low boiling dispersant solvent carrier, such as the Freons, may also be used. Water-soluble or water-dispersible granules are also useful formula¬ tions for herbicidal application of the present com¬ pounds. Such granular formulations are free-flowing, non-dusty, and readily water-soluble or water-misci- ble. The soluble or dispersible granular formulations described in U.S. patent No. 3,920,442, incorporated herein by reference, are useful herein with the pre¬ sent herbicidal compounds. The active herbicidal compounds of this invention may be formulated and/or applied with insecticides, fungicides, nematicides, plant growth regulators, fertilizers, or other agricultural chemicals and may be used as effective soil sterilants as well as selec¬ tive herbicides in agriculture. In applying an active compound of this invention, whether formulated alone or with other agricultural chemicals, an effective amount and concentration of the active compound is of course employed; the amount may be as low as, for example, 7 g/ha or lower. The active herbicidal compounds of this invention may be used in combination with other herbicides, e.g. they may be mixed with, say, an equal or larger amount of a known herbicide such as chloroacetanilide herbicides such as 2-chloro-N-(2, 6-diethylphenyl)-N- (methoxymethyl)acetamide (alachlor), 2-chloro-N-(2- ethyl-6-methylphenyl)-N-(2-methoxy-l-methylethyl)- acetamide (metolachlor) , and N-chloroacetyl-N-(2, 6- diethylphenyDglycine (diethatyl-ethyl) ; benzothia- diazinone herbicides such as 3-(l-methylethyl)-(lH)- 2,l,3-benzothiadiazin-4-(3H)-one-2,2-dioxide (benta- zon) ; triazine herbicides such as 6-chloro-N-ethyl- N-(l-methyle hyl) -l,3,5-triazine-2,4-diamine (atra- zine), and 2- [4-chloro-6-(ethylamino)-1, 3, 5-triazin- 2-ylJ-amino -2-methylpropanenitrile (cyanazine) ; dinitrolaniline herbicides such as 2, 6-dinitro-N,N- dipropyl-4-(trifluoromethyDbenzeneamine (triflura- lin) ; and aryl urea herbicides such as N'-(3,4-di- chlorophenyl)-N,N-dimethylurea (diuron) and N,N- dimethyl-N'-[ 3-(trifluoromethyl)phenylJurea (fluo- meturon) . It is apparent that various modifications may be made in the formulation and application of the com¬ pounds of this invention, without departing from the inventive concepts herein, as defined in the following claims. TABLE 1 Percent Control Pre- •Emergent Post* -Emergent PLANT A B A B Cotton 50 0 90 40 Soybean 10 0 0 10 Corn 0 0 0 0 Rice 50 20 40 0 Wheat 30 0 40 20 Field Bindweed - 60 0 40 0 Morningglory 20 0 60 10 Velvetleaf 100 0 100 0 Barnyardgrass 70 0 90 0 Green foxtail 100 70 90 0 Johnsongrass 40 0 10 0 Yellow nutsedge 30 0 10 0 TABLE 2 Cmpd. 1 Cl Cl CH, CHF 2 CH 2 CH 3 | 2 Cl Cl CH 3 CHF 2 CH(CH 3 ) CH, ui 3 LΠ F Cl CH 3 CHF 2 CH(CH 3 ) CH 3 1 4 Cl CH 3 CH 3 CHF 2 CH(CH 3 ) CH 3 5 Cl Cl CH 3 CHF 2 CH(CH 3 ) C 2 H 5 6 F Cl CH 3 CHF 2 CH(CH 3 ) G 2 H 5 7 Cl CH 3 CH 3 CHF 2 CH(CH 3 ) C 2 H 5 8 Br Br CH 3 CHF 2 CH(CH 3 ) n-C 2 H 5 9 Cl Cl CH, CHF 2 CH(CH 3 ) C 3 H 7 10 Cl Cl CH 3 CHF 2 CH(CH 3 ) CH(CH 3 ) 2 11 Cl Cl CH 3 * CHF 2 CH(CH 3 ) C 4 H 9 12 Cl Cl CH 3 CHF 2 CH(CH 3 ) CH(CH 3 )C 2 H 5 13 Cl Cl CH, CH 2 F CH(CH 3 ) C 2 H 5 TABLE 2 (Continued) Cmpd. No. X Y R 1 _ 2 _ R 3 R 4 14 F Cl CH 3 CHF 2 CH 2 ^3 15 F Cl CH 3 CHF 2 CH(CH 3 ) n-C 3 H 7 16 F Cl CH 3 CHF 2 CH(CH 3 ) CH(CH 3 ) 2 " " 17 Cl Cl CH, CHF 2 CH 2 C 2 H 5 18 Cl Cl CH 3 CHF 2 CH-CH^CH- C 2 H 5 19 F Cl CH, CHF 2 CH(CH 3 ) C(CH 3 ) 3 20 F Cl CH, CHF 2 C(CH 3 ) 2 C 2 H 5 1 21 Cl Cl m 3 CHF 2 CH 2 C(CH 3 ) 3 C3ϊ 22 F Cl CH 3 CHF 2 CH 2 C(CH 3 ) 3 23 Cl CH 2 F CH 3 CHF 2 CH(CH 3 ) C 2 H 5 24 F Cl CH 3 CHF 2 CH(CH 3 ) CH 2 CH(CH 3 ) 2 25 F F CH, CHF 2 CH(CH 3 ) C 2 H 5 26 Cl F CH, « CHF 2 CH(CH 3 ) C 2 H 5 27 Cl CH 2 F CHF 2 CH(CH 3 ) ∞S C 2 H 5 28 F CH 2 F ^3 CHF 2 CH(CH 3 ) C 2 H 5 29 F CH 3 CH 3 CHF 2 CH(CH 3 ) C 2 H 5 30 Cl CH 2 OCH 3 CH 3 ' QiF 2 CH(CH 3 ) CH, 31 Cl CH 2 S0 2 CH 3 CH 3 CHF 2 CH 2 C 2 H 5 TABLE 2 (Continued) Cmpd. No. X Y R 1 _ι 2 _ R 3 R 4 32 F CH 2 SCH 2 CH= =CH 2 CH 3 CHF 2 CH( CH 3 ) C 2 H 5 33 F CH 2 OCH 2 CH= -CH CH 3 CHF 2 CH(CH 3 ) C 2 H 5 . 34 F Cl Cl CHF 2 CH(CH 3 ) C 2 H 5 - ■ 35 F Cl C 2 H 5 CHF 2 CH(CH 3 ) C 2 H 5 36 F Cl CH 2 CN CHF 2 CH(CH 3 ) C 2 H 5 37 F Cl CH^SCH, CHF 2 CH(CH 3 ) C 2 H 5 38 F Cl αiF 2 CHF 2 CH(CH 3 ) CH, 39 F Cl CF 3 QIF 2 CH(CH 3 ) CH(CH 3 ) 2 un • -4 40 F Cl CH 2 - θ) aw 2 CH 2 C 2 H 5 41 F Cl SCH 3 CHF 2 CH(CH 3 ) CH 3 42 F Cl S0 2 CH 3 CHF 2 CH(CH 3 ) CH 3 43 F Cl CH 2 S0 2 CH 3 αi 2 CH(CH 3 ) C 2 H 5 44 F Cl CH, CH 2 F CH 2 C 2 H 5 45 F CH 2 SOCH 2 CH CH 3 [ 3 CHF 2 CH(CH 3 ) CH, TABLE 2 (Continued) Cmpd. No. X Y R 1 _ϋ 2 _ R 3 R 4 50 F CH 2 0 -<g-CH 3 CH 3 CHF 2 CH(CH 3 ) C 2 H 5 51 Cl Cl CH 3 CHF 2 CHF C 2 H S .. 52 F Cl CHF 2 CH 3 CH(CH 3 ) C(CH 3 ) 3 53 F Cl OIF 2 CH 3 CH(CH 3 ) CH 3 54 F Cl QW 2 CH 3 CH(CH 3 ) n-C 3 H 7 55 F Br αiF 2 CH 3 CH(CH 3 ) C 2 H 5 56 F Br CH, α.F 2 CH(CH 3 ) C 2 H 5 1 57 Br Br α _ F 2 CH, CH(CH 3 ) C 2 H 5 LΠ 58 F Cl CHF 2 CH 3 CH(CH 3 ) αι(cH 3 ) 2 00 1 59 F Cl CHF 2 CH 3 CH(CH 3 ) CH 2 CH(CH 3 ) 2 60 Cl Cl CΛW 2 CH 3 CH(CH 3 ) C 2 H 5 61 F Br CH 3 CHF 2 CH(CH 3 ) n-C 3 H ? 62 F CF 3 CH, CHF 2 CH(CH 3 ) C 2 H 5 63 F Br CH, fflF 2 Oi(CH 3 ) C(CH 3 ) 3 64 Cl Br CH 3 CHF 2 CH(CH 3 ) C 2 H 5 65 Br Cl CH, CHF 2 CH(CH 3 ) C 2 H 5 Other representative compounds are those which are identical with compounds 1-54, 57-60, 62, and 64-65 respectively, except that X is F and Y is Br. Still other representative compounds are those which are identical with compounds 1-61, and 63-65 respectively, except that X is F and Y is CF j . 0830W30025Wmd TABLE 3 Cmpd. No. X Y R 1 _ 2 _ R 3 R 4 Al Cl Cl CH 3 CHF 2 CH(CH 3 ) H A2 F Cl CH 3 CHF 2 CH(CH 3 ) H A3 Cl CH 3 CH 3 CHF 2 Q.(CH 3 ) H e n ID A4 F Cl CII3 CHF 2 CH(α_ 3 ) Na A5 F Cl CH 3 CHF 2 CH 2 H A6 F Cl CH, CHF 2 O.(CH 3 ) NH 3 CH(CH 3 ) 2 A7 F CH 3 m 3 CHF 2 CH(CH 3 ) H A8 F CH 3 CH 3 CHF- CH(CH 3 ) K A9 Cl CH 2 F CH 3 CHF 2 CH(CH 3 ) H A10 Cl CH 2 F CH 3 CHF 2 CH(CH 3 ) NH 4 All F Cl αiF 2 CHF 2 CH(CH 3 ) H A12 Br Cl CH 2 CN CHF 2 CH(CH 3 ) H A13 F Cl Oi 2 SCH 3 CHF 2 CH 2 H TABLE 3 (Continued) Cmpd. No. X Y R 1 _ 2 _ R 3 R 4 A14 F Cl CF 3 CHF 2 CH(CH 3 ) H A15 F CH 2 OCH 3 CH 3 CHF 2 CH(CH 3 ) H A16 F CH 3 CH 3 CHF 2 CH(CH 3 ) H A17 F CH 3 CH 3 CHF 2 CH(CH 3 ) Na A18 F CH 2 SCH 2 CH=CH 2 CH 3 CHF 2 CH(CH 3 ) H A19 F CH 2 S0 2 CH 3 CH 3 CHF 2 CH 2 HN(CH 3 ) 3 A20 F CH 2 0-^-CH 3 CH 3 CHF 2 CH(CH 3 ) H σ. o A21 F Cl CHF 2 CH(CH 3 ) H A22 F Br αiF 2 CH 3 CH(CH 3 ) H A23 F Br CH 3 CHF 2 CH(CH 3 ) H A24 Br Br CH, CHF 2 CH(CH 3 ) H A25 Br Br CHF 2 • CH 3 CH(CH 3 ) H A26 F Cl CHF 2 CH, α.(CH 3 ) Na A27 Cl Cl CHF 2 CH 3 CH(CH 3 ) H A28 Cl Br CH, cw 2 CH(CH 3 ) H A29 Br Cl CH 3 CHF, CH(CH 3 ) H Other representative compounds are those whi i are identical with compounds A1-A21, and A24-A29 respectively, except that X is F and Y is Br. Still other representative compounds are those which are identical with compounds A1-A29 respectively, except that X is F and Y is CF,. 0830 30025Wmd TABLE 4 Cmpd. No. X Y R 1 _R 2 _ R 3 ZR 4 CH(CH 3 ) OCH 2 CH(N0 2 )CH ;j CH(CH 3 ) OCH 2 CH=CH 2 I ffl(CH 3 ) 0CH 2 C≡CH as CH(CH 3 ) 0CH 2 C≡CH CH(CH 3 ) 0CH 2 CH 2 0CH 3 CH(CH 3 ) 0CH(CH 3 )C≡CH CH(CH 3 ) 0C(CH 3 ) 2 C≡CH X tt. tt, tt. tt. CJ u. ex. ex. ex. -α CM to rf us - _ • «• co σ> r-. r- r-H rH o CM tO α, o CM CM CM CM Ξ 2 pa ea pa pa pa pa p a pa pa pa pa CJ pa TABLE 4 (Continued) Cmpd. No. X Y R 1 __i 2 _ R 3 ZR 4 B24 F Cl CHF 2 CH(CH 3 ) 0CH 2 S(0)CH 3 ffl 3 B25 F Cl CH, CHF 2 CH(CH 3 ) OCH 2 S0 2 CH 3 B26 F Cl CH, CHF 2 CH(CH 3 ) ° 3 B27 F Cl CH, CHF 2 CH(CH 3 ) "Oo B28 F Cl CH 3 CHF 2 CH(CH 3 ) ° 3o 2 co B29 F Cl CH 3 CHF 2 CH(CH 3 ) <> _) B30 F Cl CH 3 CHF 2 CH(CH 3 ) OCH 2 CF 3 B31 F Cl CH, CHF 2 CH(CH 3 ) OC(CH 3 ) 2 CN B33 F Cl Q 3 CHF 2 CH(CH 3 ) SCH(CH 3 ) 2 X ex. ex, ex, ex. TABLE 4 (Continued) Cmpd. No. X R 1 - 2 _ R 3 ZR 4 B44 Cl Cl CH, CHF 2 CH(CH 3 ) °-<δ> B45 Cl Cl CH, CHF 2 cn(αι 3 ) OCH 2 SCH 3 B46 Cl Cl CHF, CH(CH 3 ) SC 2 H 5 B47 Cl Cl Qi 3 QIF 2 CH(CH 3 ) OCH-CONH- B48 Cl Cl CH 3 CHF 2 CH(CH 3 ) CTl OCH, o^ B49 Cl Cl CH 3 CHF 2 CH(CH 3 ) B52 Cl CH 3 CHF 2 CH(CH 3 ) TABLE 4 ( Continued) Cmpd. No. X Y R 1 _ 2 _ R 3 ZR 4 B53 F CH 2 OCH 3 CH, CHF 2 CH(CH 3 ) OCH 2 OCH 3 B54 F CH 2 SCH 2 CH=CH 2 CH, CHF 2 CH(CH 3 ) 0 B55 F Cl CH, CHF 2 CH(CH, B56 F Cl CH 3 CHF 2 CH(CH 3 ) o(CH 2 ) 2 o- δ) B57 F Cl α_ 3 CHF 2 CH(CH 3 ) OCH(OCOCH 3 )CH 3 B58 F Cl CH 3 CHF 2 CH(CH 3 ) 0-/v? — SCH 3 B59 Cl Cl CH 3 CH 2 F CH 2 0CH 2 C(C1)=CHC1 B60 Cl Cl CH 3 CHF 2 CH 2 OCH 2 S-< θ TABLE 4 (Continued) Cmpd. No. R J R- R ZR B63 F Cl αiF- CH, CH(CH 3 ) OCH 2 SCH 3 B64 F Cl CHF. CH(CH 3 ) OC(CH 3 ) 2 C≤CH ON B65 F Cl CHF. CH, CH(CH 3 ) SCH( CH 3 ) 2 B66 F Cl CF, CH . CH., OCH 2 CN B67 F Cl CF 2 C1 CH, CH(CH 3 ) ] B68 F CH, CHF 2 CH 2 CN CH 2 OCH 2 OCH 3 B69 F CH, QIF 2 CH 2 SCN CH(CH 3 ) OCH 2 CH 2 N(CH 3 ) ; B70 F Cl CF 3 CH 2 CH=CH 2 CH . B71 F Cl CHF 2 CH 2 OCH 3 CH, CM en to CJ r— l r-. l-. i- I rH i— l r-l r- ( i— I i-H cj cj cj cj cj cj cj cj cj cj CJ X tt. U. U tt. tt. tt, tt. tt. tt.' Cl. Cl. 3 CM tO rf iΛ ' vθ I » Cθ σ. r— I CM tO rf IΛ o. o c-» c-- c-- r-» _--. f-. f-. c-- oo eo e» eo eo oo δ 2 E a pa a pa pa cQ a pa pa a pa pa pa TABLE 4 (Continued) No. X R J R- R- ^ ZR" B86 F Cl CH, CHF. CH(CH 3 ) OCH. ®-* « X 3 ) 2 as B89 F Br CH, CHF, CH(CH 3 ) OCH 2 -g ID B90 Br Br CH, CHF, CH(CH 3 ) OCH 2 -^^ B91 F Br αι 3 CHF, CH(CH 3 ) OC(CH 3 ) 2 C≡CH B92 Cl Cl CHF CH, CH(CH,) OCH B93 F Cl αiF. CH, CH(CH 3 ) OCH. TABLE 4 (Continued) Cmpd. No. X R J R ~ R- ZR Other representative compounds are those which are identical with compounds B1-B88, B-90, and B92-B96 respectively, except that X is F and Y is Br. Still other representative compounds are those which are identical with compounds B1-B96 respectively, except that X is F and Y is CF j . Cmpd. No. X Y Λ _R _ R~ R v _R'_ Cl Cl Cl CH 3 CHF 2 CH, 11 H C2 F Cl CH 3 CHF. CH( CH 3 ) CH 3 H I C3 Cl Cl CH 3 CHF. CH(CH 3 ) S0 2 CH 3 II C4 Cl Cl CH 3 CHF. Oi(CH 3 ) S0 2 CF 3 H C5 Cl Cl CH 3 CHF 2 CH(CH 3 ) H H C6 Cl Cl CH 3 Q1F 2 CH(CH 3 ) H C7 F Cl CH 3 CHF 2 CH 2 H H C8 F Cl CH 3 CHF 2 CH- C 2 H 5 C 2 H 5 C9 F Cl CH, CHF, CH(CH 3 ) CH(CH 3 )C 2 H E H Cll Cl CH, CHF. CH(CH 3 ) 0CH 3 CH, TABLE 5 (Continued) Cmpd. No. X Y i 2 _ R 3 R 6 Jl 7 _ C12 F Cl CH 3 CHF 2 ffl(CH 3 ) CH 2 C=CH H C13 F Cl α_ 3 CHF 2 CH(CH 3 ) ^) H . ,ϊ C14 F Cl CH 3 CHF 2 CH(CH 3 ) ^3 ^3 C15 F Cl CH 3 CHF 2 CH(CH 3 ) C 2 H 5 C 2 H 5 C16 F Cl CH 3 CHF 2 CH(OI 3 ) C 2 H 5 H 1 C17 F Cl CH 3 CHF 2 CH(CH 3 ) . CH 2 C0 2 CH 3 H _o C18 F Cl CH 3 αiF 2 CH(CH 3 ) S0 2 CH 3 H , C19 F Cl CH 3 CHF 2 CH(CH 3 ) S0 2 CH 3 Na C20 F Cl CH 3 CHF 2 CH(CH 3 ) S0 2 -^)-CH 3 Na C21 F Cl CH 3 CHF 2 CH(CH 3 ) C(CH 3 ) 2 C≤CH H C22 F Cl CH 3 CHF 2 CH(Qi 3 ) C(CH 3 ) 2 CN H C23 F Cl CH 3 CHF 2 CH(CH 3 ) -(G) CH 3 C24 Cl Cl αiF. CH, CH, H H TABLE 5 (Continued) Cmpd. No. X Y R 1 _R 2 _ R 3 R 6 _R 7 _ C25 F Cl CH, CHF 2 CH(CH 3 ) H C26 F Cl CH, CHF 2 CH(CH 3 ) H H C27 F Cl CH, CHF 2 CH(CH 3 ) S0 2 CF 3 H C28 F Cl CH 3 CHF 2 CH(CH 3 ) S0 2 CF 3 Na C29 F Cl CH '3. C OHIFF 29 C CHH((CCHH 3 . )) . . - ^T Oθ))-— SSCCHH3 H ; L-O• C30 F Cl CH, CHF 2 CH(CH 3 ) S0 2 CH 3 CH 3 C31 F Cl CH, CHF 2 CH(CH 3 ) so 2 - g> CH 3 C32 F Cl CH 3 CHF 2 CH(CH 3 ) so 2 g) H C33 F Cl CH 3 CHF 2 CH 2 S0 2 CH 3 H C34 F Cl CH 3 CCHHFF 22 CCHH 22 C35 F αi 3 CH 3 CCHHFF 2 - CCHH((CCHH 3. )) NNHHCCHH 3 , H TABLE 5 (Continued) Cmpd. No. X Y _R X _ _ 2 _ R 3 R 6 ^ ? _ C36 F CH 3 CH 3 CHF 2 CH(CH 3 ) S0 2 CH 3 H C37 F CH 3 CH 3 CHF 2 CH 2 S0 2 CH 3 H C38 F Cl CH 3 CHF 2 CH(CH 3 ) -CH-CH-CH^CH '2 " ' C39 F Cl CH 3 CHF 2 CH(CH 3 ) -CH 2 CH 2 OCH 2 CH 2 - C40 F Cl αι 3 CHF 2 CH(CH 3 ) S0 2 N(CH 3 ) 2 H C41 F Cl CH 3 CHF 2 CH(CH 3 ) S0 2 NHCH(CH 3 ) 2 H C42 F Cl CH 3 CHF 2 CH(CH 3 ) C43 F Cl CHF 2 CH 3 CH(CH 3 ) C44 F Cl CF 2 C1 CH 3 CH(CH 3 ) C45 F CHF 2 CH 3 CH(CH 3 ) C48 F Cl CHF 2 CH 2 SCN Ol(CH 3 ) ri CH(CH 3 ) 2 TABLE 5 (Continued) Cmpd. No. X Y Λ 1 - _ϋ 2 _ R 3 R 6 r Rf ' C49 F Cl CF 3 CH 2 OCH 3 CH 2 CH 2 CH=CH 2 H C50 F Cl CF 3 CH 2 CH=CH 2 CH(CH 3 ) -© H C51 F Cl CHF 2 CHF 2 CH(CH 3 ) H H C52 Cl Cl CHF 2 CII3 CH 2 <ι> H C53 F Cl CH 3 CHF 2 CH(CH 3 ) CH 2 CH 2 OCH 3 II C54 F Cl CH 3 CHF 2 CH(CH 3 ) so z ^) H C55 F Cl CH 3 CHF 2 CH 2 S0 2 CH 2 CH=CH 2 H C56 F Cl CHF 2 CH 2 S0 2 CH 2 CH=CH 2 Na C57 F Cl CH, CHF 2 CH(CH 3 ) -CH 2 CH 2 CH 2 CH-CH 2 - C58 Cl CH, CHF. CH(CH 3 ) so 2 θ 11 -°2 H en o CM J CJ CJ CJ CJ CJ CJ CJ J tO u. CJ tt. ex. CJ tt. ex. ex. u. TABLE 5 (Continued) Cmpd. No. X Y R J R' R R l Λ C71 F Cl CH, CHF. CH(CH 3 ) so 2 -(o Na. C72 F Cl CH, CHF. CH(CH 3 ) II C73 Cl CH, CHF, CH(CH 3 ) so 2 -<gj)- cι H -J C75 F Cl CH, CHF, CH(CH 3 ) C76 Cl Cl CH, CHF. CH(CH 3 ) C77 F Cl CH, CHF. CH(CH 3 ) C78 Cl CH, CHF, CH( CH 3 ) TABLE 5 (Continued) Cmpd. C79 F Cl CH, CHF, CH(CH 3 ) CH 3 C80 F Cl αi, CHF, Q1(CH 3 ) H C81 F Cl CH, CHF, CH(CH 3 ) so 2 -cg>- cα H C82 F Cl CH, CHF, αι(cH 3 ) H CO C83 F Cl CH, CHF, CH(CH 3 ) so 2 -<g>- CCH, Na C85 Cl CH, CHF. CH(CH- ) so. •-Q H C86 Cl CH, CHF, CH( CH 3 ) TABLE 5 (Continued) Cmpd. No. R J _ 2 _ R 3 R 6 J R' C87 Cl CH, CHF 2 CH(CH 3 ) S0 2 " §^ (CH 3 ) 3 H C88 Cl CH, CH, CH(CH 3 ) so 2 -5) H di OCH, C91 Cl CH, CHE ¬ CH(CH 3 ) o 2 - Na OCH- C92 Cl CH, CHF. CH(CH 3 ) so 2 - Na _ 3 TABLE 5 (Continued) Cmpd. No. R J R" R * R R' C93 F Cl CH, CHF, CH(CH 3 ) S0 2 --@ CO 2 CH, H C94 F Cl CH, CHF, CH(CH 3 ) C95 F Cl CH, CHF. CH(CH 3 ) C96 F Br CH, CHF. CH(CH 3 ) C97 F Cl 01, CHF. CH(CH 3 ) -CHCH 2 CH 2 CH 2 - C0 2 CH 2 CH 3 C98 Cl CH, OIF. CH(CH 3 ) Na cζcH 3 Br C99 Cl CH, CHF. CH(CH 3 ) so 2 -<b; H OCH, TABLE 5 (Continued) Cmpd. No. R J R' R * R ^ R' ClOO Cl CH, CHF, CH(CH 3 ) Na ClOl F Cl CH, CHF, CH(CH 3 ) - ©- CN H C102 F Cl CH, CHF. CH(CH 3 ) -CHCH-SCH-,- I C0 2 CH 3 00 C103 F Cl CH, CHF, CH(CH 3 ) -CHCH 2 S0 2 CH 2 - C0 2 CH 3 C104 F Cl CH, CHF^ CH(CH,) -CHCH 2 CH 2 CH 2 CH 2 - CO- j CH^OHL C105 Cl CH, CHF. CH(CH 3 ) C106 Cl CH, CHF, αi(OI 3 ) TABLE 5 (Continued) Cmpd. No. R J R- R" R R' C107 F Cl CH, CHF. CH(CH 3 ) so 2 -(θ" H C108 F Cl CH, CHF. CH(CH 3 ) C109 F Cl CH, OIF. CH(CH 3 ) C110 F Cl CH, OIF. CH(CH 3 ) cm F Cl CH, GIF. CH(Oi 3 ) SO H TABLE 5 (Continued) Cmpd. No. X Y R J R ~ R " R R' C115 F Br CH, CHF. CH(CH 3 ) so 2 ^> H C116 F Cl CH, CHF. CH, H C117 Cl CH, CHF. CH(CH 3 ) H * oo co C118 Cl Cl CC1F, α_, CH(CH 3 ) H TABLE 5 (Continued) Cmpd. No. R J R' R~ R u R' C122 Cl Cl CHF, CH, CH(CH 3 ) C123 Br CH, CHF, CH( CH 3 ) C124 F Cl CH, CHF. αι(cn 3 ) C125 F Cl CH, CHF, CH( CH 3 ) S0 2 - ^- OCF- H C126 F Cl CH, CHF. CH(CH 3 ) C127 Cl CH, CHF. CH(CH 3 ) TABLE 5 ' (Continued) Cmpd. No. X Y R J R' R " R l R' CH(CH 3 ) 2 C128 F Cl CH, CHF. CH(CH 3 ) S0 2 - θ cΗ(CH 3 ) 2 - H CH(CH 3 ) 2 C129 F Cl CH, CHF. CH, SO. ,- ^)-OCH H C130 F Cl CH, CHF. Ok SO. OCH- Na 00 l C131 F Cl CH, CHF. CH(CH 3 ) H C132 F Cl CH, CHF, CH(CH 3 ) SO .-©- OC - Na C133 F Br CH, CHF. CH(CH 3 ) SO. CCF- H ^ C134 F Cl CH, CHF. CH(CH 3 ) soyO H OCH, TABLE 5 (Continued) Cmpd. No. R J R- R " R ^ R' C135 Cl CH, CHF, CH(CH- ) C136 Cl CH, CHF. CH(CH 3 ) C137 Cl CH . CHF. CH(CH 3 ) C138 Cl CH, CHF. CH(CH 3 ) C139 Cl CH, CHF. CH(CH 3 ) C140 Cl CH, CHF. CH(CH 3 ) t »1 TABLE 5 (Continued) Cmpd. No. R J R- R J R R' C141 Br CH, CHF, CH(CH 3 ) C142 Cl CH, CHF, CH(CH 3 C143 Cl CH, CHF, CH(CH 3 ) C144 Br CH, CHF 2 CH(CH 3 ) C145 Cl CH, CHF. CH(CH 3 ) S0 2 - 5VCCF 2 H H TABLE 5 (Continued) Cmpd. No. R J _ϋ 2 _ R 3 R 6 R' C146 Cl CH, CHF 2 CH(CH 3 ) H 0 C147 Cl CH, CHF 2 • CH(CH 3 ) S0 2 " ^ OCNHCK 3 H 00 C148 Br CH, CHF. CH(CH 3 ) C149 Cl CH, CHF. CH(CH 3 ) C150 Cl CH 3 CHF 2 CH(CH 3 ) C151 F Br CH 3 CHF 2 CH(CH 3 ) TABLE 5 (Continued) Cmpd. No. X Y R J R' R' R- R' C152 F Cl CH, CHF. CH(CH 3 ) S0 2 - ^ - N HCOCH 3 H C153 F Cl CH, CHF, CH(CH 3 ) S0 2 - g)-NH 2 H C154 Cl CH, CHF. CH(CH 3 ) C155 Cl Cl CHF. CH, CH(CH 3 ) C156 Cl Cl CH 3 CHF 2 CH(CH 3 ) C157 F Br CH, CHF 2 CH(CH 3 ) C158 F Br CH, CHF, CH(CH 3 ) TABLE 5 (Continued) Cmpd. No. X Y R J R' R- R- R' C159 F Cl CH, CHF, CH(CH 3 ) S0 2 NH 2 H. C160 F Br CH, CHF, CH(CH 3 ) H C161 F Cl CH, CHF, CH(CH 3 ) -p H ID O ∞2 C 2 H 5 C162 F Cl CH, CHF, CH(CH 3 ) * t--β H Br C163 F Cl CH, CHF, CH(CH 3 ) C164 F Cl CH, CHF, CH(CH 3 ) C165 F Cl CH, CHF. CH(CH 3 ) TABLE 5 (Continued) Cmpd. No. X Y Jl 1 .. _R 2 _ R 3 R 6 J R' C168 F Cl CH, CHF 2 CH(CH 3 ) SO 2 2 -(^-CI H I C169 F Br CH, CHF 2 CH(CH 3 ) H ID C170 F Cl CHF 2 CH, CH(CH 3 ) H C171 Br CHF. CH, CH(CH 3 ) C172 Br CH, CHF. CH(CH 3 ) TABLE 5 (Continued) Cmpd. No. X Y R 1 R ~ R R L C173 F Cl CHF CH, CH( CH 3 ) SO. ι<®P>-- OCF- H C174 F Cl CH, CHF, CH( CH 3 ) SO.-<5> OC 2 H £ II C175 Cl CH, CHF, CH(CH 3 V C176 Cl CH, CHF. CH( CH 3 ) C177 Cl CH, CHF. CH(CH 3 ) C178 F Cl CH, CHF, CH( CH 3 ) TABLE 5 (Continued) Cmpd. No. R' R R ~ R' C179 Cl CH, CHF. CH(CH 3 ) H C180 F Cl CH., CHF. CH(CH 3 ) -©-« H C181 F Cl CH, CHF. CH(CH,) - Q)-- CI H C182 F Cl CH 3 CHF. CH(CH 3 ) C183 F Cl CH, CHF. CH(CH 3 ) ~ <θ)- N ( CH 3 ) 2 H C184 F Cl CH 3 CHF. CH(CH 3 ) ^^CCF, H C185 F Br CH, CHF. CH(CH 3 ) H H C186 F Br CH, CHF. CH(CH 3 ) CH 3 H TABLE 5 (Continued) Cmpd. No. X R J _i 2 _ R 3 R 6 _R C187 Br CH, CHF 2 CH(CH 3 ) CH 3 CH C188 Br CH, CHF 2 CH(CH 3 ) C 2 H 5 H C191 F Cl CHF- αι 3 CH(CH 3 ) CH, H C192 F Cl CHF- CH 3 ■ CH(CH 3 ) CH 3 CH. C193 F Br CHF- Q1 3 CH(CH 3 ) CH, CH. C194 F Br CHF- α. 3 CH(CH 3 ) H H C195 F Br CHF 2 CH 3 CH(CH 3 ) CH 3 II C196 Br Br CHF 2 CH 3 α.(cn 3 ) CH 3 Qi C197 Br Br CHF- CH, CH(CH 3 ) H H C198 Br Br CHF 2 CH 3 CH(CH 3 ) CH 3 H C199 Br Br CH, CHF 2 CH(CH 3 ) CH, 11 TABLE 5 (Continued) Cmpd. No. X Y R 1 R 2 R 3 R 6 R 7 C200 Br Br CH, CHF. CH(CH 3 ) H H C201 F Cl CH, CHF. CH(CH,) H C202 F Cl CH 3 CHF 2 CH(CH 3 ) H VO en C203 F Cl CH 3 CHF 2 CH(CH j ) H Other representative compounds are those which are identical with compounds C1-C95, C97-C114, C116-C122, C124-C132, C134-C140, C142-C143, C145-C147, C149-C150, C152-C156, C159, C161-C165, C168, C170, C173-C184, C186, C189-C192, and C196-C203 respectively, except that X is F and Y is Br. Still other representative compounds are those which are identical with Compounds C1-C203 respectively, except that X is F and Y is CF j . 0830 30025 md TABLE 6 Identifying Properties Cmpd. Melting. - Ele ental Analysis No. Point (°C) Empirical Formula C H N 111.5-113.5 C13H11CI2F2N3O4 NMRδ CDCl3): 2.45 (s,3H), 3.80 (s,3H), 4.70 (s,2H), 6.90 (s,lH), 7.00 (t,lH,J= 58Hz), 7.50 (s,lH). NMR-S(CDCl3): 1.70 (d,3H,J=7Hz), 2.50 (s,3H) s 3.80 (s,3H), 4.80 (q,lH,J=7Hz), 7.00 (s,lH), 7.10 (t,lH,J=58Hz), 7.60 Cs,lH). Oil C14H13CIF3N3O4 NMRδ(CDCl 3 ): 1.70 (d,3H,J=7Hz), 2.50 (s,3H), 3.80 (s,3H), 4:80 (q,lH,J=7Hz), 7.00 (t,lH,J=58Hz), 7.00-7.40*(m,2H). Oil C 15 H l6 ClF 2 N3θ 4 NMR δ(CDCl3): 1.65 (d,3H,J=7Hz), 2.30 (s,3H), 2.50 (s,3H), 3.80 (s,3H), 4.80 (q,lH,J=7Hz), 6.80 (s,lH), 7.10 (t,lH,J= 58Hz), 7.40 (s,lH). NMRό(CDCl 3 ): 1.20 (t,3H,J=7Hz), 1.70 (d,3H,J=7Hz), 2.50 (s,3H), 4.20(q,2H,J= 7Hz), 4.70 (q.lH,J=7Hz), 6.95 (s,lH), 7.05 (t,lH,J=58Hz), 7.60 (s,lH). Oil C15H15CIF3N3O4 NMR δ(CDCl3): 1.20 (t,3H,J=7Hz), 1.70 (d,3H,J=7Hz), 2.50 (s,3H), 4.20 (q,2H,J= 7Hz), 4.70 (q 3 lH,J=7Hz), 7.00 (t,lH,J= 58 Hz), 7.00-7.40 (m, 2 H). TABLE 6 (Continued) Cmpd. Melting Elemental Analysis No. Point (°C) Empirical Formula C H N 7 Oil C 16 H 18 ClF 2 N3θ 4 NMRδ (CDCI3): 1.20 (t,3H,J=7Hz), 1.60 (d,3H,J=7Hz), 2.30 (s,3H), 2.50 (s,3H), 4.25 (q,2H,J=7Hz), 4.70 (q,lH,J=7Hz), 6.80 (s,lH), 7.05 (t,lH,J=58Hz), 7.30 (s,lH). 8 Oil c 15 H 15-Br2F 2 3θ4 NMRδ(CDCl3): 1.20 (t,3H,J=7Hz), 1.70 (d,3H,J=7Hz), 2.45 (s,3H), 4.15 (q,2H,J= 7Hz), 4.80 (q,lH,J=7Hz), 6.95 (s,lH), 7.10 (t,lH,J=58Hz), 7.95 (s,lH). NMRδ(CDCl 3 ): 0.90 (t,3H,J=7Hz), 1.20- 1.90 (m,5H), 2.50 (s,3H), 4.20 (t,2H,J= 7Hz), 4.80(q,lH,J=7Hz), 7.00 (s,lH), 7.10 (t,lH,J=58Hz), 7.60 (s,lH). 10 Oil C16H17CI2F2 3O4 NMRδ(CDCl 3 ): 1.20 (m,6H), 1.70 (d,3H, J=7Hz), 2.50 (s,3H), 4.60-5.30 (m,2H), 6.90 (s,lH), 7.10 (t,lH,J=58Hz), 7.60 (s,lH). 11 Oil C 17 H 1 9C1 2 F 2 3 04 NMRδ (CDCI3): 0.70-1.70 (m,7H), 1.60 (d,3H,J=7Hz), 2.45 (s,3H), 4.15 (t,2H, J=7Hz), 4.70 (q,lH,J=7Hz), 6.95 (s,lH), 7.05 (t,lH,J=58Hz), 7.60 (s,lH). 12 Oil C 17 H 19 C1 2 F 2 N 3 04 NMRδ (CDCI3): 0.70-1.80 (m,llH), 2.50 (s,3H), 4.40-5.30 (m, 2 H), 7.00 (s,lH), 7.10 (t,lH,J=58Hz), 7.60 (s,lH). 13 Oil C15HI6CI2FN3O4 C 45.94 4.11 10.71 F 46.62 4.16 12.10 NMRδ (CDCI3): 1.20 (t,3H,J=7Hz), 1.60 (d,3H,J=7Hz), 2.35 (s,3H), 4.20 (q,2H,J= 7Hz), 4.75 (q,lH,J=7Hz), 5.75 (d,2H,J=53Hz), 7.00 (s,lH), 7.60 (s,lH). TABLE 6 (Continued) C pd. Melting Elemental Analysis No. Point (°C) Empirical Formula H N 14 110-111. " C13H11CIF3N3O4 ! 15 Oil C 16 H 17 C1F 2 N 3 0 4 16 Oil C 16 H 17 C1F 3 N 3 0 4 17 118-119 C14H13CL2F2N3O4 C 42.44 3.31 10.61 F 42.60 3.58 10.53 18 Oil C 16 H 17 C1 2 F 2 N 3 0 4 C 45.30 4.04 9.90 F 44.95 3.79 9.70 19 Oil C 17 H 19 C1F3N 3 0 4 20 Oil C 16 H 17 ClF 3 N3θ 4 C 47.13 4.20 10.30 F 47.39 4.38 10.35 21 Oil C 16 H 17 C1 2 F 2 N 3 0 4 22 137-138 C 16 H 17 C1F 3 N 3 04 C 47.13 4.20 10.30 F 47.23 3.94 9.96 52 Oil C 17 H 19 C1F3N 3 0 4 Al 55-56 C 13 H 11 C1 2 F 2 N 3 04 NMRδ(CDCl 3 ): 1.70 (d,3H,J=7Hz), 2.50 (s,3H), 4.80 (q,lH,J=7Hz), 7.00 (s,lH), 7.10 (t,lH,J= 58Hz), 7.48 (s,lH), 7.50 (s,lH). A2 50-55 C13H11 LF3N3O4 NMRδ(CDCl 3 ): 1.70 (m,3H), 4.80 (m,lH), 2.40 (s,3H), 7.10-7.50 (m,3H), 8.00(bs,lH) A3 56-60 C 14 H 14 ClF 2 N3θ 4 NMRδ(CDCl3): 1.60 (d,3H,J=7Hz), 2.30 (s,3H), 2.50 (s,3H), 4.70 (q,lH,J=7Hz), 6.80 (2,1H), 7.00 (t,lH,J=58Hz), 7.30 (s,lH), 8.30 (s,lH). A 4 Solid C 13 H 10 ClF3N3Naθ4 A5 130-132 Cι HgClF3N3θ4 H 2 0 C 38.99 3.00 11.37 F 38.95 2.91 11.23 A6 70-75 CI6H20CIF3N4O4 TABLE 6 (Continued) C mpd. Melting Ele m ental Analysis No. Point CO Empirical For la H N Bl Oil Cl6 6 c -*-2F2N4θ6 NMRδ (CDCI3): 1.40-1.80 (m, 6 H), 2.50 (s, 3 H), 4.40-5.00 (m,4H), 7.00 (s,lH), 7.10 (t,lH,J= 58Hz), 7.60 (s,lH). B2 Oil C l6 H 15 Cl 2 F 2 N 3 θ4 C 45.52 3.58 9.95 F 45.24 3.46 9.87 NMRδ (CDCI3): 1.70 (d,3H,J=7Hz), 2.50 (s,3H), 4.60-5.00 (m, 3 H), 5.10-5.40 (m,2H), 5.50-6.20 (m,lH), 7.00 (s,lH), 7.10 (t,lH,J=58Hz), 7.60 (s,lH). B3 Oil C l6 H 13 Cl2F2 3 θ4 NMRδ (CDCI3): 1.70(d,3H,J=7Hz), 2.50(bs,4H), 4.60-4.90 (m,3H), 6.95 (s,lH), 7.05 (t,lH,J=58Hz), 7.60 (s,lH). B4 Oil C l6 H 13 ClF 3 N3θ4 C 47.60 3.24 10.41 F 47.88 3.31 9.68 NMRδ (CDCI3): 1.65 (d,3H,J=7Hz), 2.45 (m,4H), 4.70 (m,3H), 7.05 (t,lH,J=58Hz), 7.10-7.40 (m,2H) B5 Solid C 16 H 17 C1 2 F 2 N 3 0 5 B6 Oil C 17 H 15 C1F3N 3 0 4 c 48.87 3.62 10.06 F 46.60 3.19 10.01 B7 Oil C 18 H 17 C1F3N 3 0 4 C 50.07 3.97 9.73 F 49.68 3.75 9.40 B8 Oil C 18 H 19 C1F 3 N30 S C 48.06 4.26 9.34 F 48.31 3.77 9.00 B9 Oil C 16 H 15 C1F 3 N 3 0 6 BIO Oil C 18 H 17 C1F 7 N 3 0 4 Bll Oil C15H12CIF3N4O4 B12 Oil CI8H15CIF3N3O5 B13 Oil Cι 7 H 20 ClF3N 4 θ4 TABLE 6 (Continued) Cmpd. Melting Ele m ental Analysis No. Point CC) E pirical Formula H N B14 Oil C 17 H 17 ClF 3 N3θ 5 B15 Oil C 19 H 15 ClF 3 N3θ 4 C 51.66 3.42 9.51 F 52.15 3.43 9.49 B16 Solid C 17 H 15 C1F3N 3 06 C 45.40 3.36 9.34 F 45.00 3.25 8.90 B17 Oil C15H1SCIF3N3O3S B18 Oil C 17 H 17 ClF 3 N3θ 5 S C 43.64 3.66 8.98 F 43.50 3.73 7.99 B19 Oil C14H12CL2 3N3O4 NMRδ (CDCI3): 1.40 (t,3H,J-7Hz), 2.50 (s,3H), 4.45 (q,2H,J=7Hz), 5.95 (d,lH,J=58Hz), 7.40 (s,lH), 7.50 (t,lH,J=58Hz), 7.65 (s,lH). B21 131-136 C19H22CLF3N4O5 • B22 Oil C15H15CIF3N3OS B23 Oil C15H15CIF3N3O4S B25 Solid C 15 H 15 ClF 3 N3θ 6 S C 39.36 3.30 9.18 F 39.25 3.00 9.22 B30 Oil C 15 H 12 C1F 6 N 3 04 B31 Oil C 17 H 16 C1F 3 N 4 0 4 B33 Oil ( . I6H17CIF3N3O3S B50 Oil C 2 oH 17 ClF 3 N 3 0 4 S B57 Oil C 17 H 17 ClF 3 N3θ 6 C 45.19 3.79 9.30 F 45.68 3.77 8.22 NMRδ CDCI3/DMSO do): 2.20 (s,3H), 4.60 (s,2H), 7.30 (bs,3H), 7.40 (5,lH,J=58Hz), 7.65 (s,lH). TABLE 6 (Continued) Cmpd. Melting Elemental Analysis No. Point CO E mpirical Form uLa C H N C2 Oil C 14 H 14 C1F3N 4 03 NMRδ (CDC1 3 ): 1.60 (d,3H,J=7Hz), 2.50 (s,3H), 2.90(d,3H,J=7Hz), 4.75 (q 5 lH,J=7Hz), 6.80(bs,lH), 7.10 (t,lH,J=58Hz), 7.20-7.45 (m,2H). C3 185-188 C 14 H 14 Cl2F 2 4θ5S C 36.61 3.07 12.20 F 36.79 3.01 12.41 NMRδ(CDCl3): 1.70 (d,3H,J=7Hz), 2.50 (s, 3 H), 3.40 (s,3H), 4.80(q,lH,J=7Hz), 7.10 (s,lH), 7.10 (t,lH,J=58Hz), 7.70 (s,lH). C4 Oil Cl4HnCl 2 F 5 N 4 0 5 S C 32.76 2.16 10.92 F 32.80 2.05 8.77 NMRδ (CDCI3): 1.70 (d,3H,J=7Hz), 2.50 (s,3H), 4.90(q,lH,J=7Hz), 7.10 (s,lH), 7.10 (t,lH,J=58Hz), 7.60 (s,lH), 8.50(bs,lH). C5 132-135 Gl3Hi2Cl 2 F 2 N 4 0 3 ' C6 142-144 C 1 4H 14 Cl2F 2 N 4 0 3 C7 173-175 Cl2HiθClF 3 N 4 0 3 C8 105-110 C 16 H 18 C1F 3 N 4 0 3 C9 Oil C 17 H 20 C1F 3 N 4 0 3 CIO Solid C 20 H 18 C1F3N 4 0 5 S C 46.29 3.50 10.80 F 46.77 4.12 11.03 Cll Oil C 15 H 16 C1F3N 4 0 4 C 44.07 3.94 13.71 F 38.44 3.67 11.28 C12 Solid C16H14CIF3N4O3 C 47.71 3.50 13.91 F 46.03 3.60 13.91 C13 57 C 19 H 16 C1F 3 N 4 03 C 51.77 3.66 12.71 F 50.90 4.00 11.88 C14 Oil C 15 H 16 C1F 3 N 4 0 3 C15 Solid Cl 7 H 0ClF3 4O3 C16 Oil C15H16CIF3N4O3 TABLE 6 (Continued) Cmpd. Melting Ele ental Analysis No. Point ( β C) Empirical Formula C H N C17 Solid " . C 16 H 16 C1F3N 4 0 5 C18 145-150 C14H14CIF3N4O5S C19 Solid C 1 H 1 4ClF3N 4 aOsS C20 Solid C 2 oH 17 ClF3N 4 Na0 5 S C21 O ' il C 18 H 18 C1F 3 N 4 03 C 50.18 4.21 13.00 F 50.95 3.91 12.38 C22 Oil C 17 H 17 C1F 3 N 5 03 C23 Oil C20H18CIP3N4O3 C25 Solid C19H15CI2F3N4O5S C 42.31 2.80 10.39 F 40.44 2.91 8.56 C26 142-143 C13H12CLF3N4O3 C32 127-134 C 19 H 16 C1F3N 4 0 5 S C38 47-54 C 17 H 18 C1F 3 N 4 0 3 C 48.75 4.33 13.38 F 47.06 3.73 12.36 C42 Oil C21H18CLF3N4O5S C43 162-166 C19H15CI2F3N4O5S C59 100-105 C 21 H 18 C1F 3 N 4 0 7 S C 44.81 3.40 9.95 F 42.20 2.81 9.61 C69 Solid Cι 9 H 16 ClF3N 4 0 5 S C 45.20 3.19 11.10 F 44.74 3.55 10.59 C70 208-208.5 C18H13CI2F3N4O5S C 41.16 2.49 10.67 F 44.11 3.08 10.96 C71 Solid C 19 H 14 Cl 2 F 3 N4θ5SNa C72 135-140 C 20 H 18 ClF3N 4 O S S C73 Solid Cι 9 H 15 Cl 2 F3N 4 05S C74 110 C19H15C1F3N507S TABLE 6 (Continued) Cmpd. Melting Elemental Analysis No. Point CO , Empirical Formula C H N C75 175-180. ' C19H14CI3F3N4O5S C76 171-173 C 19 H 15 C1 3 F 2 N 4 05S C77 66-70 C 19 H 15 C1F 4 N 4 0 5 S C78 248-253 C 22 H 22 C1F 3 N 4 0 S S C79 Solid C 21 H 20 C1F 3 N 4 0 5 S C80 67-70 C 20 H 15 C1F 6 N 4 0 5 S. C81 58-62 C 20 H 18 C1F 3 N 4 0 6 S C82 Solid C 20 H 18 C1F 3 N 4 0 5 S C83 108-113 C 20 H 17 ClF3N 4 O6SNa C84 155-157 C 20 H 17 Cl 2 F 3 N 4 O 5 S C 43.41 3.10 10.13 F 42.65 3.30 9; 19 C85 69-74 C 17 H 14 C1F 3 N 4 0 5 S 2 C86 Solid C 19 H 20 ClF 3 N 4 O 5 C87 Solid C 23 H 24 C1F 3 N 4 0 5 S C 49.24 4.31 9.99 F 46.40 4.21 8.63 C88 Solid C 19 H 17 C1 2 FN 4 0 5 S C89 Solid C 18 H 18 C1F 3 N 4 0 5 C90 168-172 C 21 H 20 C1F 3 N 4 0 7 S C91 Solid C 21 H 19 ClF 3 N 4 0 7 SNa C92 Solid C 20 H 17 ClF 3 N 4 O 5 SNa C93 173-179 C 21 H 18 C1F 3 N 4 0 7 S C94 65-70 C 19 H 15 C1 2 F 3 N 4 0 5 S C95 110 C 19 Hi5BrClF 3 N 4 0 5 S C 39.09 2.59 9.60 F 38.75 2.66 9.64 C97 Solid C20H22CIF3N4O3 TABLE 6 (Continued) Cmpd. Melting Ele m ental Analysis No. Point CO Empirical Formula C H N C98 Solid C 21 H 17 ClF 3 N 0 7 SNa C99 Solid C 20 H 17 BrClF 3 N 4 O 6 S ClOO Solid C 20 H 16 BrClF3N4O6SNa ClOl Solid C 2 oH 15 ClF3N 5 0 5 S C 45.33 2.85 13.22 F 44.83 2.42 13.06 C102 60-70 C 18 H 18 C1F 3 N 4 0 5 S C 43.69 3.67 11.32 F 43.24 4.01 10.71 C103 80-95 C 18 H 18 C1F N 4 0 7 S C104 Oil C21H24CIF3N4O5 C105 Solid C21H20CIF3N4O7S C106 Solid C 21 H 19 ClF 3 N4θ 7 SNa C107 170 C 19 H 15 C1F3N 5 0 7 S C108 Solid C 18 H 19 C1F 3 N 5 0 4 C109 Oil C 22 H 22 C1F 3 N 4 0 6 S C110 85-90 C 22 H 21 ClF 3 N 4 0 6 SNa cm Oil C 19 H 16 C1F 3 N 4 0 6 S C112 174-176 C 20 H 18 C1F 3 N 4 0 7 S C113 Oil C 2 oH 17 Cl 2 F3N 4 0 5 S C114 60-70 C 2 oH 16 Cl 2 F3N 4 θ5SNa C115 Solid C 19 H ls BrClF 3 N4θ 5 S C116 188-191 C 2 oH 16 ClF 3 N 4 θ7S C117 >230 C 2 3H 18 C1F 3 N 4 0 5 S C118 144-147 C 2 iH 19 Cl 3 F 2 N 0 7 S C119 211-212 C20H18C1F3 4O7S TABLE 6 (Continued) Cmpd. Melting Elemental Analysis No. Paint CO E-mpiiical Formula H N C120 Solid C 20 H 17 ClF3N4θ 7 SNa C121 Solid C 20 H 17 ClF 3 N 4 O 7 SNa C122 105-110 C 2 iH 2 oCl 2 F 2 N 4 0 7 S C123 163-166 C 21 H20BrF 3 N SO 7 C124 Solid C21H21CIF3N5O5S C125 Solid C 2 oH 15 ClF 6 N θ6S C126 Solid C 2 oH 17 ClF 3 Ns0 7 S C127 Solid C28H34CIF3N4F O5S C128 Solid C 28 H33ClF 3 N4θsSNa C129 147-149 C 19 H l6 ClF3N4θ6S C 43.81 * 3.10 10.76 F 44.31 3.26 10.54 C130 Solid C 19 H 1S ClF3N4θ6SNa C131 198-201 • C 23 H 22 C1F3N 4 0 6 S C 48.05 3.86 9.74 F 47.11 3.89 9.34 C132 Solid C 20 H 14 ClF 6 N 4 O 6 SNa C133 Solid C 20 H 1 sBrF 6 N 4 θ5S C134 65-68 C 2 oH 17 ClF 4 N4θ6S C135 68-72 C 2 oH l7 ClF 4 N 4 θ6S C136 Solid C 21 H 2 oClF 3 N 4 0 6 S C137 130-134 C 2 oH 17 ClF 4 N4θ3 C138 136-140 C23H18CIF3N4O5S C139 Solid C 21 H 19 ClF3N4θ6SNa 0833W30080 md Table 7 Preemergence Herbicidal Activity Compound No. ' : ; 1 2 3 4 Rate (kg/ha) - 2.0 4.0 2.0 2.0 %κ %c %C %κ %c %κ %c Species Cotton 100 100 100 50 Soybean 0 90 30 0 Field Corn 80 100 100 30 Rice 50 100 90 30 Wheat 0 100 100 30 Field Bindweed 100 100 100 100 Morningglory 100 100 60 0 Velvetleaf 100 100 Nϋ 100 Barnyardgrass 90 100 100 100 Green Foxtail 100 100 100 ND Johnsongrass 80 100 100 95 Yellow Nutsedge 70 • 100 100 0 Compound No. 6 7 8 9 Rate (kg/ a) 2.0 2.0 2.0 2.0 *K -C %K -C _K %C %κ %c Species Cotton 100 60 70 100 Soybean 10 30 20 20 Field Corn 70 30 20 80 Rice 80 50 60 90 Wheat 100 80 40 90 Field Bindweed 100 60 80 100 Morningglory 100 70 90 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 90 90 90 100 Yellow Nutsedge 100 so 80 100 Table 7 (Cont. ) Preemergence Herbicidal Activity Compound No.- . Rate (kg/ha)* Species Cotton 100 40 100 30 Soybean 20 100 30 20 Field Corn 100 40 20 20 Rice 90 90 70 10 Wheat 90 70 50 10 Field Bindweed 100 100 90 20 Morningglory 100 100 100 50 Velvetleaf 100 100 100 80 Barnyardgrass 100 100 100 40 Green Foxtail 100. 100 100 40 Johnsongrass 100 100 90 40 Yellow Nutsedge 100 • 90 90 10 Compound No. 1 4 1 5 16 17 Rate (kg/ha) 1 . 0 170 T70~ TΌ F IT TK re %κ T Spec ies Cotton 90 100 100 100 Soybean 0 40 30 0 Field Corn 60 40 100 30 Rice 30 80 90 30 Wheat 20 100 100 10 Field Bindweed 100 90 100 90 Morningglory 90 100 90 90 Velvetleaf 100 100 100 90 Barnyardgrass 50 100 100 90 Green Foxtail 10 100 100 10 Johnsongrass 60 90 90 80 Yellow Nutsedge 100 90 100 60 Table 7 (Cont. ) Preemergence Herbicidal Activity Compound No;; : • 18 19 20 21 Rate (kg/ha). ' 0.5 2.0 0.5 2.0 . • TK — τz τz — τz τi — τz τ — sr Species Cotton 10 80 30 80 Soybean 20 100 0 20 Field Corn 10 80 0 80 Rice 0 90 20 30 Wheat 0 50 0 0 Field Bindweed 0 100 90 100 Morningglory 0 90 90 90 Velvetleaf 30 100 100 100 Barnyardgrass 0 100 50 100 Green Foxtail 90 100 100 100 Johnsongrass 0 90 30 90 Yellow Nutsedge 0 ■ 100 10 70 Compound No, 51 52 Rate (kg/ha) 2.0 2.0 . c H _C Species Cotton 70 100 Soybean 10 70 Field Corn 30 100 Rice 40 95 Wheat 0 100 Field Bindweed 90 100 Morningglory 80 95 Velvetleaf 100 100 Barnyardgrass 30 100 Green Foxtail 20 100 Johnsongrass 80 100 Yellow Nutsedge 40 100 Table 7 (Cont. ) Preemergence Herbicidal Activity Compound No.- . Rate (kg/ha) * Species Cotton 100 10 80 Soybean 0 0 20 Field Corn 0 0 0 Rice 80 10 70 Wheat 80 20 100 Field Bindweed 100 30 50 Morningglory 100 10 0 Velvetleaf 100 ND 100 Barnyardgrass 100 40 100 Green Foxtail 100 100 ND Johnsongrass 80 30 95 Yellow Nutsedge 90 20 0 Compound No. A4 A. Bl B2 Rate (kg/ha) 1. ,0 0. 5 2, .0 2. 0 %K %c .C .C %K %c Species Cotton 90 80 100 100 Soybean 10 30 10 10 Field Corn 40 30 30 90 Rice 80 30 90 90 Wheat 80 30 70 90 Field Bindweed 70 70 100 100 Morningglory 90 90 100 100 Velvetleaf 100 90 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 90 80 90 100 Yellow Nutsedge 90 80 100 100 Table 7 (Cont.) Preemergence Herbicidal Activity Compound No.- Rate (kg/ha) Species Cotton 100 90 100 100 Soybean 0 40 20 10 Field Corn 30 80 50 40 Rice 70 80 90 90 Wheat 80 90 90 90 Field Bindweed 90 100 100 90 Morningglory 100 90 90 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 100 90 100 90 Yellow Nutsedge 100 • 90 100 100 Compound No , B 7 B 8 B 9 B10 Rate (kg/ha) 1.0 2.0 0.5 1.0 _K %C %K -C %κ %c %K %C Species Cotton 100 100 100 20 Soybean 30 50 20 0 Field Corn 80 100 30 30 Rice 90 90 60 30 Wheat 80 90 40 70 Field Bindweed 100 100 80 100 Morningglory 100 100 60 90 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 80 100 50 80 Yellow Nutsedge 100 100 100 70 - I l l - Table 7 (Cont. ) Preemergence Herbicidal Activity Compound No.. • Bll B12 B13 B14 Rate (kg/ha) ' 1. .0 1.0 1.0 1.0 • K %C .K %C %κ %c .K %C Species Cotton 100 100 90 100 Soybean 10 10 100 20 Field Corn 60 20 90 40 Rice 60 60 90 80 Wheat 90 50 90 90 Field Bindweed 100 70 100 90 Morningglory 90 90 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 90 ' 80 90 90 Yellow Nutsedge 100 90 90 90 Compound No. BIS B16 B17 • B18 Rate (kg/ha) 2.0 1.0 1.0 2.0 .K _C %κ %c C %κ %c Species Cotton 100 80 100 100 Soybean 70 20 40 30 Field Corn 90 60 80 60 Rice 90 60 80 80 Wheat 90 50 90 90 Field Bindweed 100 90 80 100 Morningglory 100 100 • 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 90 100 Johnsongrass 100 90 90 90 Yellow Nutsedge 100 100 100 100 Table 7 (Cont. ) Preemergence Herbicidal Activity Compound No.- ■ B21 B22 B23 B25 Rate (kg/ha) ' * 1.0 0.5 1.0 1.0 u %c %κ %c κ %c % .c Species Cotton 90 60 70 70 Soybean •0 0 0 50 Field Corn 50 0 30 70 Rice 40 40 80 60 Wheat 50 10 60 50 Field Bindweed 90 20 90 70 Morningglory 90 40 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 80 90 100 Green Foxtail 90 80 100 100 Johnsongrass 40' 20 70 90 Yellow Nutsedge 90 . 90 80 90 Compound No. B30 B31 B32 B33 Rate (kg/ha) 0.5 1.0 0.5 1.0 K %c .K .C %κ %c %κ %c Species Cotton 100 100 20 80 Soybean 0 10 0 40 Field Corn 10 20 20 90 Rice 20 50 20 90 Wheat 20 30 10 60 Field Bindweed 20 70 30 90 Morningglory 50 80 30 90 Velvetleaf 100 100 90 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 50 80 50 70 Yellow Nutsedge 100 90 90 90 Table 7 (Cont. ) Preemergence Herbicidal Activity Cotton 50 100 Soybean 20 10 Field Corn 30 40 Rice 40 50 Wheat 60 60 Field Bindweed 10 90 Morningglory 50 70 Velvetleaf 100 100 Barnyardgrass 90 100 Green Foxtail 100 100 Johnsongrass 50- 70 Yellow Nutsedge 50 90 Compound No. Cl C2 C3 C Rate (kg/ha) 2.0 1.0 2.0 2.0 . h %- .C .K .C .K %C Species Cotton 70 100 100 40 Soybean 40 100 40 0 Field Corn 60 100 80 0 Rice 20 100 80 0 Wheat 20 100 90 40 Field Bindweed 100 100 100 80 Morningglory 100 100 100 90 Velvetleaf 100 100 100 100 Barnyardgrass 80 100 100 90 Green Foxtail 90 100 100 90 Johnsongrass 80 100 100 50 Yellow Nutsedge 80 100 100 50 Table 7 (Cont. ) Preemergence Herbicidal Activity Compound No. C5 C6 C7 C8 Rate (kg/ha)- • • 2.0 2.0 1.0 2.0 τ % T τz τt τz %κ %c Species Cotton 100 100 100 90 Soybean 100 90 10 100 Field Corn 100 100 100 100 Rice 100 100 40 100 Wheat 100 100 30 100 Field Bindweed 100 100 100 100 Morningglory 100 90 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 90 100 Johnsongrass ιoα 100 90 100 Yellow Nutsedge 100 100 100 90 Compound No. C9 CIO Cll C12 . Rate (kg/ha) 1.0 1.0 1.0 1.0 ■ S t, %K -C %κ %c %κ %c Species Cotton 80 100 100 100 Soybean 90 90 100 100 Field Corn 100 20 100 100 Rice 90 80 " 100 100 Wheat 100 70 100 100 Field Bindweed 100 100 100 100 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 100 90 100 100 Yellow Nutsedge 80 60 100 100 Table 7 ( Cont . ) Preemergence Herbicidal . Activity Compound No. . . C13 C14 C15 C16 Rate (kg/ha) • 2.0 2.0 2.0 2.0 ' , %K -C ._. *C %κ %c %K %C Species Cotton 100 100 100 100 Soybean 100 100 100 100 Field Corn 90 100 100 100 Rice 100 100 100 100 Wheat 90 100 100 100 Field Bindweed 100 100 100 100 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 100- 100 100 100 Yellow Nutsedge 100 100 100 100 Compound No. C17 C18 C19 C20 Rate (kg/ha) 2.0 1.0 1.0 1.0 %K %C %κ %c %κ %c %K IC Species Cotton 100 100 100 100 Soybean 100 0 20 80 Field Corn 100 70 100 50 Rice 90 80 60 30 Wheat 90 50 40 10 Field Bindweed 100 80 80 100 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 100 90 90 40 Yellow Nutsedge 100 90 80 10 Table 7 (Cont. ) Preemergence Herbicidal Activity Compound No.. . C21 C22 C23 C24 Rate (kg/ha) ■ ' 1.0 1.0 1.0 1.0 • . %κ %c 1κ z %K %C %K %C Species Cotton 100 100 30 40 Soybean 90 100 50 10 Field Corn 100 100 90 80 Rice 80 100 20 30 Wheat 100 100 70 0 Field Bindweed 100 100 100 90 Morningglory 100 100 100 100 Velvetleaf 100 100 100 90 Barnyardgrass 100 100 100 80 Green Foxtail 100 100 100 100 Johnsongrass 100- 100 100 70 Yellow Nutsedge 80 100 40 30 Compound No. C25 C26 C32 C38 Rate (kg/ha) 2.0 1.0 1.0 1.0 .K _C %κ %c IK %c %κ %c Species Cotton 100 100 100 90 Soybean 30 100 40 100 Field Corn 70 100 20 100 Rice 60 90 50 100 Wheat 30 100 10 100 Field Bindweed 100 100 100 100 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 90 100 80 100 Johnsongrass 70 100 80 100 Yellow Nutsedge 80 100 40 ND Table 7 ( Cont . ) Preemergence Herbicidal Activity Compound No . • C42 C43 C59 C69 Rate ( kg /ha) 1.0 1.0 1.0 0.5 κ c %κ %c %κ % c %κ % c Species Cotton 90 100 100 40 Soybean 70 70 50 10 Field Corn 40 70 70 30 Rice 60 90 80 30 Wheat 70 70 40 0 Field Bindweed 100 100 100 90 Morningglory 100 100 100 80 Velvetleaf. 100 100 100 100 Barnyardgrass 100 100 100 20 Green Foxtail 100 100 100 20 Johnsongrass 60 ' 95 100 40 Yellow Nutsedge 70 • 100 70 70 Compound No. . C70 C71 C72 C73 * Rate (kg/ha) 1.0 1.0 1.0 1.0 *<_ .K %c %κ .C %K -C Species Cotton 100 100 100 80 Soybean 20 50 50 30 Field Corn 30 50 60 30 Rice 70 40 30 40 Wheat 20 40 20 50 Field Bindweed 100 100 100 100 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 20 90 100 90 Green Foxtail 0 40 95 100 Johnsongrass 80 - 60 90 80 Yellow Nutsedge 90 40 60 20 Table 7 (Cont. ) Preemergence Herbicidal Activity Compound No.. , - C74 C75 C76 C77 Rate (kg/ha) ' 1.0 1.0 1.0 1.0 %C %K %C %K %C %K .C Species Cotton 100 90 60 95 Soybean 80 30 30 40 Field Corn 0 50 20 30 Rice 40 60 30 70 Wheat 30 40 .20 60 Field Bindweed 90 100 100 100 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 85 95 100 100 Green Foxtail 100 95 70 100 Johnsongrass 70 * 80 40 95 Yellow Nutsedge 20 . 30 30 30 Compound No. C78 C79 C80 C81 Rate (kg/ha) 1.0 1.0 1.0 1. .0 .K %<_ %K -C .K %C %κ IC Species Cotton 80 50 60 100 Soybean 40 0 20 100 Field Corn 30 10 0 50 Rice 50 50 20 50 Wheat 40 20 30 100 Field Bindweed 100 80 100 100 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 80 95 100 Green Foxtail 90 100 100 100 Johnsongrass 40 80 95 100 Yellow Nutsedge 30 20 0 80 Table 7 (Cont. ) Preemergence Herbicidal Activity Compound No. . C82 C83 C84 C85 Rate (kg/ha)- • 1.0 1.0 1.0 1.0 9- x t>. .rC <kIK k* < rC <%s- xK s %_rC <k %C Species Cotton 100 95 10 100 Soybean 10 95 0 30 Field Corn 20 20 10 95 Rice 30 40 20 80 Wheat 20 30 0 80 Field Bindweed 100 100 30 100 Morningglory 100 100 100 100 Velvetleaf 100 100 90 ' 100 Barnyardgrass 95 95 10 100 Green Foxtail 100 90 30 100 Johnsongrass 95 80 30 100 Yellow Nutsedge 10 20 ND ND Compound No. Rate (kg/ha) Species Cotton 100 30 0 90 Soybean 70 20 10 30 Field Corn 100 10 10 60 Rice 90 40 0 90 Wheat 90 10 0 80 Field Bindweed 100 100 0 100 Morningglory 100 100 0 100 Velvetleaf 100 100 10 100 Barnyardgrass 100 95 40 100 Green Foxtail 100 0 0 100 Johnsongrass 100 30 10 95 Yellow Nutsedge ND ND ND ND Table 7 (Cont. ) Preemergence Herbicidal Activity Compound No, • C90 C91 C92 C93 Rate (kg/ha) ' • 1.0 1.0 1.0 1.0* %κ c κ %c %c %κ %c Species Cotton 100 100 100 20 Soybean 100 90 30 0 Field Corn 80 80 20 30 Rice 80 90 40 50 Wheat 70 50 30 10 Field Bindweed 100 100 100 80 Morningglory 100 100 100 80 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 0 Johnsongrass 100- 95 80 30 Yellow Nutsedge ND . ND ND ND Compound No. C94 C95 C97 • 098 Rate (kg/ha) 1.0- i.o 1.0 0. 5 %K .c %K %C %κ %c %κ .C Species Cotton 80 100 100 100 Soybean 20 60 20 30 Field Corn 20 20 70 40 Rice 20 30 80 20 Wheat 0 10 70 20 Field Bindweed 100 100 100 100 Morningglory 100 100 100 100 Velvetleaf 100 100 * 100 100 Barnyardgrass 60 40 100 90 Green Foxtail 50 50 100 80 Johnsongrass 60 60 90 95 Yellow Nutsedge ND ND ND ND Table 7 (Cont. ) Preemergence Herbicidal Activity Compound No. Rate (kg/ha) Species Cotton 80 80 95 30 Soybean 70 50 30 20 Field Corn 30 60 10 50 Rice 20 60 20 80 Wheat 10 20 10 50 Field Bindweed 100 100 90 20 Morningglory 100 100 100 80 Velvetleaf 100 100 100 100 Barnyardgrass 10 70 60 100 Green Foxtail 100 80 40 100 Johnsongrass 80. 80 50 80 Yellow Nutsedge ND ND ND ND Compound No. C103 C104 C105 C106 Rate (kg/ha) 0.5 0.5 0.5 0.5 *<_ %K %C %K %<_ .K %C Species Cotton 30 30 100 100 Soybean 10 10 95 90 Field Corn 30 9.0 70 30 Rice 50 80 95 90 Wheat 30 80 50 30 Field Bindweed 40 100 100 100 Morningglory 60 90 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 95 95 100 100 Green Foxtail 100 100 100 100 Johnsongrass 80 95 100 100 Yellow Nutsedge ND ND ND ND Table 7 (Cont. ) Preemergence Herbicidal Activity Compound No, . . C107 C108 C109 C110 Rate (k /ha)- * 0.5 0.5 0.5 0.5 ~ n τz τ τz τt τz %κ %c Species Cotton 90 100 70 30 Soybean 10 95 90 95 Field Corn 20 100 100 100 Rice 40 95 95 90 Wheat 0 95 100 100 Field Bindweed 80 90 95 100 Morningglory 95 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 40 80 100 100 Green Foxtail 0 100 100 100 Johnsongrass 50 * 100 100 100 Yellow Nutsedge ND . ND ND ND Compound No. cm C112 C113 C11.4 Rate (kg/ha) 0.5 ' 0.5 0.5 0.5 .K *C %κ %c .K %C %κ %c Species Cotton 20 90 50 30 Soybean 40 40 0 0 Field Corn 10 0 10 10 Rice 70 20 20 20 Wheat 50 10 10 10 Field Bindweed 70 100 100 90 Morningglory 70 90 90 95 Velvetleaf 90 100 100 100 Barnyardgrass 100 40 50 70 Green Foxtail 100 80 30 70 Johnsongrass 70 95 30 70 Yellow Nutsedge ND ND ND ND Table 7 (Cont.) Preemergence Herbicidal Activity Compound No. C115 C116 C117 C118 Rate (kg/ha) - ; 0.5 0.5 0.5 0.5 ~ n ΪZ _κ %c τt τz K %C Species Cotton 80 95 50 20 Soybean 30 0 95 0 Field Corn 10 10 10 10 Rice 10 20 30 0 Wheat 30 10 0 10 Field Bindweed 100 90 100 80 Morningglory 100 95 100 50 Velvetleaf 100 100 100 50 Barnyardgrass 50 80 40 10 Green Foxtail 90 40 80 10 Johnsongrass 90. 80 20 10 Yellow Nutsedge ND ND ND ND Compound No. C119 C120 C121 C122 Rate (kg/ha) 0.5 0.S 0.5 0.5 %K C U .C " .C .K .C Species Cotton 50 70 95 70 Soybean 30 20 20 50 Field Corn 10 10 20 40 Rice 30 20 30 0 Wheat 30 10 10 10 Field Bindweed 100 100 100 100 Morningglory 100 90 90 80 Velvetleaf 100 100 100 100 Barnyardgrass 50 80 70 70 Green Foxtail 0 0 20 50 Johnsongrass 70 70 90 100 Yellow Nutsedge ND ND ND ND Table 7 (Cont. ) Preemergence Herbicidal Activity Compound No. . Rate (kg/ha) Species Cotton 50 20 20 Soybean 50 60 30 Field Corn 0 70 10 Rice 60 80 10 Wheat 10 60 10 Field Bindweed 100 100 80 Morningglory 100 95 90 Velvetleaf 100 100 100 Barnyardgrass 100 100 30 Green Foxtail 10 100 50 Johnsongrass 100 100 10 Yellow Nutsedge ND ND ND Table 8 Postemergence Herbicida .1 Activi" _£ Compound No. . 1 2 3 4 Rate (kg/ha) ■ • 2.0 4.0 2.0 2.0 ' , %κ %c H .(. κ %c .C Species Cotton 100 100 100 90 Soybean 40 0 60 0 Field Corn 90 100 100 0 Rice 80 100 100 80 Wheat 10 100 90 90 Field Bindweed 100 100 100 100 Morningglory 100 100 100 70 Velvetleaf 100 100 ND 100 Barnyardgrass 100 100 100 90 Green Foxtail 100 100 ND ND Johnsongrass 90* 95 100 70 Yellow Nutsedge 50 50 100 0 Compound No. 6 7 8 • 9 Rate (kg/ha) 2.0 2.0 2.0 2.0 h k C .K %c %K %C -C Species Cotton 100 90 100 100 Soybean 50 40 50 30 Field Corn 100 40 30 100 Rice 100 80 90 70 Wheat 100 90 30 80 Field Bindweed 100 100 100 100 Morningglory 100 80 100 80 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 100 100 70 80 Yellow Nutsedge 100 70 30 80 Tabl e 8 ( Cont . ) Postemergence Herbicida .1 Activity Compound No. 10 11 12 13 Rate (kg/haj- . 2.0 2. .0 2.0 2.0 ._. ,C %K IC %K %C %K %C Species Cotton 100 100 100 70 Soybean 30 50 30 20 Field Corn 100 60 30 10 Rice 90 90 50 30 Wheat 100 90 70 20 Field Bindweed 100 100 100 50 Morningglory 30 100 100 80 Velvetleaf 100 100 100 80 Barnyardgrass 90 100 100 80 Green Foxtail 100 100 100 40 Johnsongrass 80 80 90 30 Yellow Nutsedge 90 90 50 20 Compound No. 14 15 16 17 Rate (kg/ha) T7CT T7TF THT 7D " % C % C . K % C U % C Spec ies Cotton 100 100 100 100 Soybean 60 40 30 70 Field Corn 10 30 10 70 Rice 30 90 30 30 Wheat 10 60 40 20 Field Bindweed 100 100 90 90 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 70 Green Foxtail 90 100 100 20 Johnsongrass 80 90 80 70 Yellow Nutsedge 30 80 90 30 Table 8 (Cont.) Postemergence Herbicidal Activity Compound No.. 18 19 20 21 Rate (kg/ha) ' * 0.5 2.0 0.5 2.0 %K ' %C %κ .c .c %κ %c Species Cotton 100 100 90 80 Soybean 30 40 40 20 Field Corn 60 50 30 20 Rice 20 50 20 30 Wheat 20 30 30 20 Field Bindweed 50 80 40 90 Morningglory 50 90 80 100 Velvetleaf 80 100 100 100 Barnyardgrass 10 80 80 . 40 Green Foxtail 60 80 60 30 Johnsongrass so- 40 10 40 Yellow Nutsedge io . 90 10 30 Compound No. 51 52 Rate (kg/ha) 2.0 ϋ ~ .K .C %c Species Cotton 70 100 Soybean 50 95 Field Corn 10 100 Rice 30 90 Wheat 10 100 Field Bindweed 90 100 Morningglory 100 100 Velvetleaf 90 100 Barnyardgrass 70 100 Green Foxtail 10 100 Johnsongrass 40 100 Yellow Nutsedge 30 100 Tabl ^ e 8 (Cont. ) P Poosstteemmeerrggence Herbicidal Activity Compound No. Al A2 A3 Rate (kg/ha) - ■ 4.0 2.0 2.0 « %C %K %C K %C Species Cotton 100 90 100 Soybean 0 20 0 Field Corn 0 30 0 Rice 30 20 90 Wheat 30 30 80 Field Bindweed 100 80 100 Morningglory 100 70 - 60 Velvetleaf 100 ND 100 Barnyardgrass 100 90 100 Green Foxtail 100 ND ND Johnsongrass 75- 60 95 Yellow Nutsedge 0 10 0 Compound No. A4 A6 Bl • -B2 Rate (kg/ha) 1.0 0.5 2.0 2.0 .K %C %κ %c %K %C %K -C Species Cotton 100 90 100 100 Soybean 40 20 10 30 Field Corn 40 20 40 30 Rice 20 30 50 80 Wheat 90 90 100 100 Field Bindweed 90 10 100 100 Morningglory 100 90 100 40 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 90 100 100 Johnsongrass 60 30 80 80 Yellow Nutsedge 100 50 40 80 Table 8 (Cont.) Postemergence Herbicida .1 Activity Compound No. B3 B4 B5 B6 Rate (kg/ha) • 2.0 1.0 2.0 1.0 _ %C %K %C « %C U .C Species Cotton 100 100 100 100 Soybean 30 40 60 60 Field Corn 70 30 20 100 Rice 90 90 80 100 Wheat 90 100 90 100 Field Bindweed 100 100 100 90 Morningglory 80 90 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 90 80 90 80 Yellow Nutsedge 30 90 60 100 Compound No, B7 B8 B10 Bll Rate (kg/ha) 1.0 2.0 1.0 1.0 ._. _C .K %C _κ %c U -C Species Cotton 100 100 100 100 Soybean 60 80 20 30 Field Corn 100 70 0 0 Rice 100 100 20 30 Wheat 100 100 10 100 Field Bindweed 100 100 100 100 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 80 70 90 90 Yellow Nutsedge 80 70 20 100 Table 8 (Cont. ) Postemergence Herbicidal Activity Compound No. B12 B13 B14 B15 Rate (kg/ha) ' T7ΪT TTϋ " 1.0 270 K ~ τz τt τz τt τz %κ r Species Cotton 100 100 100 100 Soybean 30 100 90 80 Field Corn 10 60 20 60 Rice 20 50 80 90 Wheat 100 90 80 100 Field Bindweed 100 100 90 100 Morningglory 100 100 90 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 30. 100 60 100 Yellow Nutsedge 90 100 70 90 Compound No. B16 B17 " B18 B21 Rate (kg/ha) 1.0 1.0 2.0 1.0 .K %C .K %C %K -C %K %C Species Cotton 100 100 100 100 Soybean 40 40 50 30 Field Corn 30 30 20 30 Rice 50 30 90 20 Wheat 100 40 70 100 Field Bindweed 100 100 100 100 Morningglory 80 90 100 100 Velvetleaf 100 100 100 90 Barnyardgrass 100 70 100 100 Green Foxtail 100 100 100 100 Johnsongrass 40 30 40 10 Yellow Nutsedge 100 60 90 80 Table 8 (Cont.) Postemergence Herbicidal Activity Compound No. Rate (kg/ha). Species Cotton 80 100 80 80 Soybean 30 10 30 10 Field Corn 20 40 90 10 Rice 70 90 50 70 Wheat 90 80 90 100 Field Bindweed 50 100 100 50 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 60 100 100 Green Foxtail 100 100 100 100 Johnsongrass 10. 100 50 10 Yellow Nutsedge 10 90 90 10 Compound No. B31 B32 B33 B50 Rate (kg/ha) 1.0 0.5 1.0 0.5 I ϋ ¥1 ¥C * .K C - K Spec i es Cotton 100 100 100 100 Soybean 20 10 30 30 Field Corn 40 0 40 20 Rice 40 20 40 40 Wheat 80 70 100 40 Field Bindweed 100 80 100 70 Morningglory 90 100 100 100 Velvetleaf 90 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 50 0 40 30 Yellow Nutsedge 90 0 60 20 Table 8 ( Cont . ) Postemergence Herbicidal Activity Compound No. B57 Cl Rate (kg/ha): ; 0.5 2.0 ._. .<_ %K %C Species Cotton 100 100 Soybean 30 30 Field Corn 30 70 Rice 90 20 Wheat 90 0 Field Bindweed 80 100 Morningglory 100 100 Velvetleaf 100 100 Barnyardgrass 100 100 Green Foxtail 100 100 Johnsongrass 40, 80 Yellow Nutsedge 60 60 Compound No , C2 C-3 C 4 C5 Rate (kg/ha) 1.0 2.0 2.0 2.0 K %C %κ %c %K %C %K %C Species Cotton 100 100 70 100 Soybean 90 40 40 90 Field Corn 100 100 40 100 Rice 100 70 50 100 Wheat 100 40 30 100 Field Bindweed 100 90 100 100 Morningglory 100 100 90 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 90 100 Green Foxtail 100 100 90 100 Johnsongrass 100 90 40 90 Yellow Nutsedge 100 30 20 100 Table 8 (Cont. ) Postemergence Herbicidal Activity Cotton 100 100 100 90 Soybean 90 60 90 80 Field Corn 100 50 90 80 Rice 100 80 80 50 Wheat 100 10 80 60 Field Bindweed 100 100 100 90 Morningglory. 100 100 100 80 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 60 100 Green Foxtail 100 100 100 100 Johnsongrass 100, 90 80 90 Yellow Nutsedge 100 80 60 20 Compound No. CIO . Cll C12 C13 Rate (kg/ha) 1.0 1.0 1.0 2.0 .K %C %K C .K .c u *c Species Cotton 100 100 100 100 Soybean 100 90 90 80 Field Corn 60 100 100 100 Rice 60 100 100 100 Wheat 60 100 100 100 Field Bindweed 60 90 100 100 Morningglory 100 100 100- 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 80 90 100 100 Yellow Nutsedge 10 100 100 100 Table 8 ( Cont . ) Postemergence Herbicidsil Activity Compound No. C14 C15 C16 C17 Rate (kg/ha); - 2.0 2, .0 2.0 2.0 %C %K .(_ %K %C % K %c Species - • Cotton 100 100 100 100 Soybean 100 90 100 100 Field Corn 100 90 100 100 Rice 70 50 90 100 Wheat 100 100 100 100 Field Bindweed 100 100 100 90 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 100 90 100 50 Yellow Nutsedge 100 90 100 100 Compound No. C18 C 9 C20 C21 Rate (kg/ha) 1.0 1.0 1.0 1.0 ΪF ~ τz τ τz τi τz ,κ Species Cotton 100 100 100 100 Soybean 40 40 100 100 Field Corn 30 20 0 100 Rice 10 10 20 60 Wheat 100 100 100 100 Field Bindweed 100 100 100 100 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 100 100 Johnsongrass 90 100 40 100 Yellow Nutsedge 100 60 10 80 Table 8 (Cont. ) Postemergence Herbicidal Activity Compound No. C22 C23 C24 C25 Rate (kg/ha) T7u ~ TTtJ 1 . 0 T70 " τr TZ τ — τz τi — z τr T Species Cotton 100 100 50 100 Soybean 100 80 20 70 Field Corn 100 80 20 60 Rice 80 30 10 50 Wheat 100 90 10 60 Field Bindweed 100 100 100 100 Morningglory 100 80 90 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 80 100 Green Foxtail 100 100 100 100 Johnsongrass 100. 100 60 100 Yellow Nutsedge 80 40 0 70 Compound No. C26 C32 C38 Rate (kg/ha) 1.0 1. .0 1.0 k ϋ -C u .C %κ %c Species Cotton 100 100 100 Soybean 80 80 100 Field Corn 100 20 100 Rice 90 50 100 Wheat 90 50 100 Field Bindweed 100 100 70 Morningglory 100 100 100 Velvetleaf 100 100 100 Barnyardgrass 100 100 100 Green Foxtail 100 80 100 Johnsongrass 90 40 90 Yellow Nutsedge 90 20 ND Table 8 (Cont.) Postemergence Herbicida .1 Activity Compound No. . C42 C43 C59 C( )9 Rate (kg/ha) • • 1. .0 1. .0 1.0 0. .5 k k c %K . ( _ %κ %c . K %C Species Cotton 100 100 100 100 Soybean 100 90 80 50 Field Corn 100 100 80 80 Rice 60 SO 40 60 Wheat 90 95 80 90 Field Bindweed 100 100 100 100 Morningglory 95 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 95 100 100 100 Green Foxtail 100 100 100 50 Johnsongrass 95- 100 95 60 Yellow Nutsedge 40 95 100 50 Compound No, C70 C71 C72 C73 Rate (kg/ha) • 1.0 1.0 1.0 1.0 %κ %c %κ %c %κ %c %K .C' Species Cotton 90 100 100 100 Soybean 60 60 70 85 Field Corn 40 60 50 30 Rice 30 40 60 60 Wheat 40 95 30 80 Field Bindweed 100 100 100 100 Morningglory 100 .100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 90 Green Foxtail 30 100 60 90 Johnsongrass 70 50 50 70 Yellow Nutsedge 40 20 60 30 Table 8 (Cont. ) Postemergence Herbicidal Activity Compound No. Rate (kg/ha) : Species Cotton 85 95 95 100 Soybean 90 90 80 80 Field Corn 40 100 70 100 Rice 60 40 40 30 Wheat 50 40 30 100 Field Bindweed 95 100 100 100 Morningglory 100 100 95 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 95 95 95 Green Foxtail 85 100 95 100 Johnsongrass 50- 80 40 70 Yellow Nutsedge 30 10 20 30 Compound No. C78 C79 C80 C81 Rate (kg/ha) 1.0 1.0 1.0 l.ό kK k kt k C u %c %κ %c Species Cotton 100 100 100 100 Soybean 100 50 80 100 Field Corn 100 20 40 80 Rice 30 20 10 90 Wheat 90 40 40 95 Field Bindweed 100 50 100 100 Morningglory 100 60 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 40 100 Green Foxtail 90 95 100 100 Johnsongrass 60 80 40 100 Yellow Nutsedge 20 70 20 20 Table 8 ( Cont . ) Postemergence Herbicida .1 Activity Compound No. C82 C83 C84 α 35 Rate (kg/ha). 1 .0 1 .0 1.0 1. ,0 * kt . ( _ %<_ %c % K .C Species Cotton 100 100 80 100 Soybean 80 100 40 90 Field Corn 100 95 40 95 Rice 70 60 20 95 Wheat 90 90 30 80 Field Bindweed 100 100 20 95 Morningglory 100 100 90 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 95 100 Green Foxtail 100 100 30 100 Johnsongrass 100 95 20 90 Yellow Nutsedge 0 60 ND ND Compound No. C86 C87 C88 . C89 Rate (kg/ha) 2.0 1.0 1.0 1.0 %K %C kK k C %κ .c %K C Species Cotton 100 90 10 90 Soybean 80 100 30 90 Field Corn 100 100 20 100 Rice 100 50 10 70 Wheat 100 60 10 100 Field Bindweed 100 100 10 95 Morningglory 100 100 20 100 Velvetleaf 100 100 20 100 Barnyardgrass 100 100 20 100 Green Foxtail 100 80 50 100 Johnsongrass 100 30 30 80 Yellow Nutsedge ND ND ND ND Table 8 ( Cont . ) Postemergence Herbicida .1 Activity Compound No. C90 C91 C92 C< 33 Rate (kg/ha) - : 1.0 1 .0 1.0 1. ,0 *K -C .K *C « c . K %C Species Cotton 100 100 100 100 Soybean 100 100 90 70 Field Corn 95 100 100 70 Rice 60 90 70 30 Wheat 100 100 80 80 Field Bindweed 100 100 100 70 Morningglory 100 100 100 95 Velvetleaf 100 100 100 100 Barnyardgrass 100 100 100 100 Green Foxtail 100 100 80 95 Johnsongrass 100. 100 70 30 Yellow Nutsedge ND ND ND ND Compound No. C94 C95 C97 C98 Rate (kg/ha) 1.0 1.0 1.0 0.5 * ._. k k k C %c %κ %c Species Cotton 100 100 95 90 Soybean 80 95 95 70 Field Corn 50 95 100 70 Rice 30 70 95 70 Wheat 40 100 100 90 Field Bindweed 95 100 95 100 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 80 90 95 95 Green Foxtail 95 100 100 70 Johnsongrass 60 70 95 90 Yellow Nutsedge ND ND ND ND Tabl e 8 ( Cont . ) Postemergence Herbicidal Activity Compound No. C99 ClOO ClOl C102 Rate (kg/ha) : ; 0.5 0.5 0.5 0.5 %K %c %κ %C -K %c %κ %c Species Cotton 90 100 100 100 Soybean 100 100 60 SO Field Corn 100 100 50 60 Rice 40 40 20 70 Wheat 100 100 40 95 Field Bindweed .100 100 90 90 Morningglory 100 100 90 100 Velvetleaf 100 100 100 95 Barnyardgrass 100 100 30 60 Green Foxtail 90 100 10 100 Johnsongrass 100 90 50 70 Yellow Nutsedge ND ND ND ND Compound No. C103 - C104 • C105 C106 Rate (kg/ha) 0.5 0.5 0.5 0.5 τ — τz i — τz τ — τz τr Species Cotton 100 80 100 100 Soybean 30 80 100 100 Field Corn 30 90 95 100 Rice 40 70 95 95 Wheat 30 90 100 100 Field Bindweed 95 50 100 100 Morningglory 95 90 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 60 95 100 100 Green Foxtail 100 95 100 100 Johnsongrass 70 80 100 100 Yellow Nutsedge ND ND ND ND Tabl e 8 ( Cont . ) Postemergence Herbicida 1 Activity Compound No. Rate (kg/ha) . ; Species Cotton 100 100 95 80 Soybean 60 100 95 100 Field Corn 60 100 80 90 Rice 20 95 80 80 Wheat 20 100 95 95 Field Bindweed 100 100 100 100 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 95 100 100 100 Green Foxtail 90 100 100 100 Johnsongrass 60 100 100 100 Yellow Nutsedge ND ND ND ND Compound No. •=» cm C112 C113 * C114 Rate (kg/ha) 0.5 0.5 0.5 0.5 %K k C k k C %κ %c C Species Cotton 40 90 80 95 Soybean 50 90 40 50 Field Corn 20 40 30 30 Rice 20 20 30 80 Wheat 70 90 30 30 Field Bindweed 60 100 100 100 M.orningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 100 95 30 70 Green Foxtail 100 100 80 90 Johnsongrass 95 95 40 30 Yellow Nutsedge ND ND ND ND Table 8 ( Cont . ) Postemergence Herbicida L1 Activit X Compound No. C115 C116 C117 Cl .18 Rate (kg/ha): * 0.5 0.5 0.3 0. 5 %K %C IK %C %c %κ %C Species Cotton 20 100 100 40 Soybean 30 60 100 95 Field Corn 30 40 100 100 Rice 10 20 0 10 Wheat 30 60 95 60 Field Bindweed 10 80 100 95 Morningglory 30 100 100 80 Velvetleaf 20 100 100 100 Barnyardgrass 20 70 100 60 Green Foxtail 30 70 100 40 Johnsongrass 30 80 70 20 Yellow Nutsedge ND ND ND ND Compound No . Rate (kg/ha) Species Cotton 95 80 100 95 Soybean 95 95 80 80 Field Corn 40 60 10 60 Rice 10 10 20 10 Wheat 90 100 100 100 Field Bindweed 100 100 100 95 Morningglory 100 100 100 100 Velvetleaf 100 100 100 100 Barnyardgrass 50 50 80 100 Green Foxtail 70 20 30 80 Johnsongrass 60 40 80 80 Yellow Nutsedge ND ND ND ND Table 8 (Cont. ) Postemergence Herbicidal Activity Compound No. C123 C124 C125 Rate (kg/ha) IT. 5 0.3 0.3 TF ~ τz τi — τz τi τz Species Cotton 100 100 100 Soybean 100 100 100 Field Corn 90 100 100 Rice 90 70 0 Wheat 100 100 100 Field Bindweed 100 100 100 Morningglory 100 100 100 Velvetleaf 100 100 100 Barnyardgrass 95 100 95 Green Foxtail 95 100 95 Johnsongrass 95 95 90 Yellow Nutsedge ND ND ND

Claims: Cl a ims : 1. An herbicidal compound of the general formula in which R 1 is halogen, alkyl, haloalkyl, cyano¬ alkyl, arylalkyl, alkoxyalkyl, alkylthio, alkylsul- finyl, alkylsulfonyl , alkylthioalkyl, alkylsulfinyl¬ alkyl or alkylsulfonylalkyl ; R 2 is CHF 2 or CH 2 F; X is Br, Cl, F or haloalkyl; Y is Br, Cl , F, methyl, * haloalkyl, or a radical of the formula R 8 OCH 2 -, R 8 SCH--, R 8 SOCH 2 - or R 8 S0 2 CH 2 - where R is C, -C. alkyl, C--C- alkenyl, C,-C ς alkynyl, phenyl, or substituted phenyl; R is alkylene or haloalkylene; and 4 R is alkyl. 2. A carboxvlic acid of the formula or a salt of said carboxylic acid, in which R is halogen, alkyl, haloalkyl, cyanoalkyl, arylalkyl, alkoxyalkyl, alkylthio, alkylsulfiny , alkylsulfonyl, alkylthioalkyl, alkylsul inylalkyl , or alkylsul on lalk l; R 2 i s CIIF 2 or CH 2 F ; X is Br, Cl, F or haloalkyl; SUBSTITUTE SHEET Y is Br, Cl, F, methyl, haloalkyl, or a radical of the formula R 8 0CH--, R 8 SCH 2 -, R 8 SOCH 2 - or R 8 S0 2 CH 2 - where R is C-i-C, alkyl, C 2 ~C-. alkenyl, C,-Cr alkynyl, phenyl or substituted phenyl; and 3 ' . R is alkylene or haloalkylene. 3. An herbicidal compound of the general formula in which X is Br, Cl, F or ' aloalkyl ; Y is Br, Cl, F, methyl, haloalkyl, or a radical of the formula R 8 OCH 2 -, R 8 SCH--, R 8 SOCH 2 ~ or R 8 S0 2 CH 2 > where R is c ι ~ C alkyl, 2 -C 5 alkenyl, C3-C5 alkynyl, phenyl or substituted phenyl; Z is oxygen or sulfur; R is alkylene or haloalkylene; 4 R is substituted alkyl, alkenyl, alkynyl, or a monovalent cyclic group having a ring of 5 or 6 atoms whose valence is on a carbon atom of said ring; R is halogen, alkyl, haloalkyl, cyanoalkyl, arylalkyl, alkoxyalkyl, alkylthio, alkylsulfinyl, alkylsul onyl, alkylthioalkyl, alkylsul inylalkyl or alkylsulfonylalkyl ; 7 R" is alkyl, haloalkyl, alkenyl, alkynyl, cyanoalkyl, thiocyanoalkyl or a group of the formula: -alkylene-Y' -R in which said alkylene group has 1 to 5 carbon atoms, Y' is oxygen or S(0)r in which r is 0 to 2, and R is alkyl, alkenyl or alkynyl; the substituent an said substituted alkyl of R 4 being nitro, halo, furyl o tetrahydrofuryl, acetyl, cyano -C0-N is the residue of ammonia or a primary or secondary amine, -C00R where R is the residue of an alcohol, phenyl or substituted phenyl, alkylamino, dialkylamino, or a trialkylammonium salt, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, or phenoxy, phenylthio, phenylsul inyl, or phenyl¬ sulfonyl. 4. An herbicidal compound of the general formula in which X is Br, Cl, F or haloalkyl; Y is Br, Cl, F, methyl, haloalkyl, or a radical of the formula R 8 0CH 2 -, R 8 SCH 2 -, R 8 S0CH 2 - or R 8 S0 2 CH 2 ~ where R is C, -C, alkyl, C--C,. alkenyl, C,-Cr alkynyl, phenyl, or substituted phenyl; R is alkylene or haloalkylene; R is halogen, alkyl, haloalkyl, cyanoalkyl, arylalkyl, alkoxyalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl or alkylsul onylalkyl ; R 2 is alkyl, haloalkyl, alkenyl, alkynyl, cyanoalkyl, thiocyanoalkyl, or a group of the formula -alkylene-Y' -R in which said alkylene group has 1 to 5 carbon atoms, Y' is oxygen or S(0)r in which r is 0 to 2, and R is alkyl, alkenyl or alkynyl; and N >. η " is NH- or the residue of a primary or secondary amine or of a sulfonamide. 5. A compound as in claim 4 in which -N 7 is R a residue of a sulfonamide. /R 6. A compound as in claim 5 in which -N 7 is the residue of an alkylsulfonamide or a haloalkyl- sulfonamide. 7. A compound as in claim 5 in which the residue of an arylsulfonamide, 8. A compound as in claim 5 in which s the residue of an amine. 9. A compound as in claim 7 in which said aryl- sulfonamide is a halophenyl, alkoxyphenyl, or alkyl- phenylsulfonamide. 10. An herbicidal compound of the general formula in which X is Br, Cl, F or haloalkyl; Y is Br, Cl, F, methyl, haloalkyl, or a radical of the formula R 8 0CH 2 ~, R 8 SCH 2 -, R 8 S0CH 2 - or R 8 S0 2 CH 2 - where R is C-^C.- alkyl, -C 2 -C 3 alkenyl, C j -Cς alkynyl, phenyl, or substituted phenyl; R is alkylene or haloalkylene; R is halogen, alkyl, haloalkyl, cyanoalkyl, arylalkyl, alkoxyalkyl, alkylthio, alkylsul inyl, alkylsul onyl, alkylthioalkyl, alkylsul inylalkyl or alkylsul onylalkyl; R 2 is alkyl, haloalkyl, alkenyl, alkynyl, cyanoalkyl, thiocyanoalkyl, or a group of the formula: -alkylene-Y' -R in which said alkylene group has 1 to 5 carbon atoms, Y' is oxygen or S(0)r in which r is 5 0 to 2, and R is alkyl, alkenyl or alkynyl, and OR 9 is the residue of an oxime. 11. An herbicidal composition comprising an herbicidally effective amount of the compound of claim 1 in admixture with a suitable carrier. 12. A method for controlling undesired plant growth which comprises applying to the locus where control is desired an herbicidally effective amount of the composition of claim 11. 13. An herbicidal composition comprising an herbicidally effective amount of the compound of claim 2 in admixture with a suitable carrier. 14. A method for controlling undesired plant growth which comprises applying to the locus where control is desired an herbicidally effective amount of the composition of claim 13. 15. An herbicidal composition comprising an herbicidally effective amount of the compound of claim 3 in admixture with a suitable carrier. 16. A method for controlling undesired plant growth which comprises applying to the locus where control is desired an herbicidally effective amount of the composition of claim 15. 17. An herbicidal composition comprising an herbicidally effective amount of the compound of claim 4 in admixture with a suitable carrier. 18. A method for controlling undesired plant growth which comprises applying to the locus where control is desired an herbicidally effective amount of the composition of claim 17. 19. An herbicidal composition comprising an herbicidally effective amount of the compound of claim 10 in admixture with a suitable carrier. 20. A method for controlling undesired plant growth which comprises applying to the locus where control is desired an herbicidally effective amount of the composition of claim 19. 21. Process which comprises reacting a com¬ pound of the formula with a compound of the formula MR CON where R \R rad.ical or a f luoralkylene rad ical and or the residue of a primary or secondary amine or of a sulfonamide and M is a reac¬ tive leaving substituent, to form a compound of the formula in which, in said formulas: X is bromine, chlorine, or fluorine or haloalkyl; Y is bromine, chlorine, fluorine, methyl, halo¬ alkyl, or a radical of the formula R 8 0CH 2 -, R 8 SCH 2 -, R 8 S0CH 2 - or R 8 S0 2 CH 2 - where R 8 is C 1 -C 3 alkyl, C_-C_alkenyl, or C_-C,.alkynyl, phenyl or sub¬ stituted phenyl ; R is halogen, alkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, arylalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl , alkylthioalkyl, alkylsul inylalkyl or alkylsulfonylalkyl; and 2 R is alkyl, haloalkyl, alkenyl of 2 to 5 car¬ bon atoms, alkynyl of 3 to 5 carbon atoms, cyanoalkyl, thiocyanoalkyl or a group of the formula -alkylene- Y -R in which said alkylene group has 1 to 5 carbon atoms, Y being oxygen or S(0) in which r 5 is 0 to 2, and R being alkyl, alkenyl of 2 to 5 carbon atoms or alkynyl of 3 to 5 carbon atoms. 22. Process as in claim 21 in which R is arylsulfonyl and R is hydrogen. 23. Process which comprises forming a compound of the formula and reacting said compound with a compound of the formula MR 3 C00R 4 where R is an alkylene or luoroalkylene radical, R is alkyl and M_ is a reactive leaving substituent to form a compound of th.e formula in which, in said formulas: X is bromine, chlorine, or fluorine or haloalkyl; Y is bromine, chlorine, fluorine, methyl, haloalkyl, or a radical of the formula R 8OCH 2 ' R 8 SCH 2 -, R 8 SOCH 2 - or R 8 S0 2 CH 2 - where R 8 is C-.-C,alkyl, C 2 -C ς alkenyl, or C,-C,-alkynyl, phenyl or substituted phenyl; R is halogen, alkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, arylalkyl, alkylthio, alkylsul inyl, alkylsulfonyl, alkylthioalkyl, alkylsul inylalkyl or alkylsulfonylalkyl.; and R 2 is CHF 2 or CH 2 F. 24. Process which comprises forming a compound of the formula and reacting said compound with a compound of the formula MR 3 COZR 4 where M is a reactive leaving substituent, R is alkylene or luoralkylene, Z is 0 or S and 4 R is a substituted alkyl group, an alkenyl group, an alkynyl group or a monovalent cyclic group having a ring of 5 or 6 atoms whose valence is on a carbon atom of said ring to form a compound of the ormula in which, in said formulas: X is bromine, chlorine, or fluorine or haloalkyl; Y is bromine, chlorine, fluorine, methyl, halo¬ alkyl, or a radical of the formula R 8 0CH--, R 8 SCH--, - R 8 SOCH 2 - or R 8 S0 2 CH 2 - where R 8 is (^-C j alkyl, C 6 -C-.alkenyl, or C,-C_alkynyl, phenyl or substituted phenyl ; R is halogen, alkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, arylalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl , alkylthioalkyl, alkylsulfinylalkyl or alkylsulfonylalkyl; and 2 R is alkyl, haloalkyl, alkenyl of 2 to 5 carbon atoms, alkynyl of 3 to 5 carbon atoms, cyano¬ alkyl, thiocyanoalkyl or a group of the formula -alkylene-Y -R in which said alkylene group has 1 to 5 carbon atoms, Y being oxygen or S(0) in 5, r which r is 0 to 2, and R being alkyl, alkenyl of 2 to 5 carbon atoms or alkynyl of 3 to 5 carbon atoms. 25. Process which comprises forming a compound of the formula and reacting said compound with a compound of the formula MR 3 COOR 9 where M is a reactive leaving substituent, R is 9 alkylene or fluoroalkylene and -OR is the residue of an oxime to form a compound of the formula in which, in said formulas: X is bromine, chlorine, or fluorine or haloalkyl; Y is bromine, chlorine, fluorine, methyl, halo- alky, or a radical of the formula R '8 OCH 2 >, R 8 SCH 2 -, R 8 S0CH 2 - or R 8 S0 2 CH 2 - where R 8 is C-^C.-alkyl, C -C.alkenyl, or C,-C,.alkynyl, phenyl or substituted phenyl; R is halogen, alkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, arylalkyl, alkylthio, alkylsul inyl, alkylsul onyl, alkylthioalkyl, alkylsulfinylalkyl or alkylsul onylalkyl; and 2 R is alkyl, haloalkyl, alkenyl of 2 to 5 carbon atoms, alkynyl of 3 to 5 carbon atoms, cyano¬ alkyl, thiocyanoalkyl or a group of the formula -alkylene-Y -R in which said alkylene group has 1 to 5 carbon atoms, Y being oxygen or S(0) in 5 r which r is 0 to 2, and R being alkyl, alkenyl of 2 to 5 carbon atoms or alkynyl of 3 to 5 carbon atoms. 26. Process which comprises reacting (a) a 2- luorophenyl hydrazine whose 4-position is unsubstituted, with (b) a reagent or reagents which converts the hydrazine group, -NHNH 2 , to a triazolinone ring having the formula so as to form a N-2- luorophenyl triazolinone, and subsequently halogenating with chlorine or bromine at said unsubstituted 4-position. 27. Process as in claim 26 in which said 2-fluorophenyl hydrazine has a nitro or alkoxy group at the 5-position of the .benzene ring.

Inventors: MARAVETZ LESTER LAWRENCE, MARAVETZ, LESTER, LAWRENCE
Applicants: FMC CORP, FMC CORPORATION
Application year: 1985
Main classification: C07D249
IPC codes: A01N43, C07D249, C07D401, C07D403, C07D405, C07D409, C07D417