HERBICIDAL 1-ARYL-4-SUBSTITUTED-1,4-DIHYDRO-5H-TETRAZOL-5-ONES AND SULFUR ANALOGS THEREOF

Abstract: Herbicidal aryltetrazolinones and thiones of formula (I), in which W is oxygen or sulfur; R is alkyl, fluoroalkyl, alkenyl, haloalkenyl, cyanoalkyl, alkylthioalkyl, haloalkoxyalkyl, trifluoromethylthio or alkoxyalkyl; one of X<1> and X<2> is fluorine, chlorine, or bromine and the other is fluorine, chlorine, bromine, alkyl, or haloalkyl; and Z is hydrogen or a group selected from a variety of substitutents and is preferably a 2-propynyloxy group.

Description: HERBICIDAL 1-ARYL-4-SUBSTITUTED-1 ,4-DIHYDRO-5H-TETRAZOL- 5-ONES AND SULFUR ANALOGS THEREOF The invention described in this application pertains 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 a series of novel herbicidal 1-aryl-5-tetra- zolinones and thiones, herbicidal compositions of them, methods of preparing them, and methods for preventing or destroying undesired plant growth by preemergence or postemergence application of the herbicidal compositions to the locus where control is desired. Also disclosed are intermediates useful in the preparation of the herbicidal compounds. The present herbicidal compounds may be used to effectively control a variety of both grassy and broadleaf plant species. The present inven¬ tion is particularly useful in agriculture, as a number of the novel aryltetrazolinones described herein show a selectivity favorable to soybean, cotton, wheat, lima bean, corn, sorghum, or other crops at application levels which inhibit the growth of or destroy a variety of weeds. 1-Phenyl-5 (4H)-tetrazolinone, formula A below wherein Y and R are hydrogen, is believed to be the first 1-aryl-5-tetrazolinone reported in the literature. The compound was made by M. Freund et al. and described in Ber., 28, 78 (1895). In the almost ninety years since disclosure of the parent compound, only a handful of substituted derivatives of it have been described in the literature. 1-(Monosubstituted-phenyl)-5-tetrazolinones of formula A are disclosed in a paper by J.P. Horwitz et al. in J.Am. Chem. Soc. , 81 , 3076 (1959). In the disclosed compounds, Y is methyl, methoxy, chloro, bromo, nitro, or amino and R is hydrogen. 0. Tsuge et al., J. Org. Chem., 45, 5130 (1980), disclose a number of the compounds disclosed by Horwitz et al. , above, and additional compounds of formula A wherein the phenyl group is unsubstituted (Y is hydro¬ gen) and R is phenylaminocarbonyl, acetyl, or 2-methyl- propanoyl. J-M. Vandensavel et al., J. Org. Chem. , 38, 675 (1973), report the preparation of compounds of formula A above wherein Y is hydrogen and R is n-butyl or " 4-chlorophenylsulfonyl, Y is nitro and R is n-butyl or cyclohexyl, and Y is chloro or methoxy and R is 4-chlorophenylsulfonyl. J.K. Elwood et al., J. Org. Chem., 32, 2956 (1967), - describe compounds of formula A wherein Y is hydrogen and R is 2-propenyl, 1-methyl-2-propenyl, or 2-butenyl. Additional compounds of formula A wherein R is methyl and Y is hydrogen, chloro, or nitro, or R is benzyl and Y is chloro are disclosed by A. Vollmar et al., J. Heterocycl. Chem., 11 , 491 (1974). None of the disclosed compounds above have been described in the references as having herbicidal pro- • perties. The present invention provides a series of herbi- cidal compounds of the formula wherein is oxygen or sulfur; R is alkyl (preferably of 1 to 6 carbon atoms), haloalkyl (preferably of 1 to 5 carbon atoms), alkoxy¬ alkyl (preferably of 2 to 6 carbon atoms), alkylthio- alkyl (preferably of 2 to 6 carbon atoms), cyanoalkyl (preferably of 1 to 5 alkyl carbon atoms), haloalkoxy¬ alkyl (preferably of 2 to 6 carbon atoms), trifluoro¬ methylthio, alkenyl (preferably of 2 to 5 carbon atoms), or haloalkenyl (preferably of 2 to 5 carbon atoms); and 1 2 One of X and X is fluorine, chlorine, or bromine and the other is fluorine, chlorine, bromine, alkyl (preferably of 1 to 6 carbon atoms) such as methyl, or haloalkyl (preferably of 1 to 5 carbon atoms) such as bromomethyl, fluoromethyl, or trifluoromethyl. When 1 2 X is fluorine, chlorine, or bromine, X may be selected from the substituents above and nitro. Z is defined below. Separate aspects of the invention pertain to sub-genera for the individual substituent groups above. In one such aspect W will be oxygen. In a sub-genus for R, that group may be alkyl of 1 to 6 carbon atoms such as n-C_H_, a fluoroalkyl radical of 1 to 5 carbon atoms and one or more fluorine atoms, especially a fluoropropyl radical such as 3-fluoro- propyl, alkoxyalkyl or alkylthioalkyl of 2 to 4 carbon atoms such as methoxymethyl or its thio analog, cyano- • alkyl of 1 to 3 alkyl carbon atoms such as cyanomethyl, fluoroalkoxyalkyl of 2 to 4 carbon atoms, for example, 2-(difluoromethoxy)ethyl, alkenyl of 3 to 5 carbon atoms such as 2-propenyl, or haloalkenyl of 3 to 5 carbon atoms, for example, a fluoroalkenyl such as 3-fluoro-2- propenyl. In a preferred embodiment R is n-C-H- or a fluoropropyl radical such as 3-fluoropropyl. Typical R groups include -CH 3 , -CH 2 CH 3 , -(CH 2 ) 2 CH 3 , -CH(CH 3 ) 2 , -(CH 2 ) 3 CH 3 , -CH 2 CH(CH 3 ) 2 , -CH(CH 3 )CH 2 CH 3 , -CHP j , -CH 2 CH 2 F, -(CH 2 ) 2 CH 2 F, -(CH 2 ) 2 CH 2 Br, -(CH^CHF^ -CH 2 CHFCH 3 , -CH 2 CF 2 CH 3 , -CH 2 OCH 3 , -CH 2 OCH 2 CH 3 , -CH 2 SCH 3 , -CH 2 CN, -CH 2 CH 2 OCHF 2 , -SCF 3 , -CH=CH 2 , -CH 2 CH=CH 2 , and -CH r) CH=CHF. • * 1 2 1 With respect to sub-genera for X and X , X may be fluorine, chlorine, bromine, methyl, or tri- 2 fluoromethyl and X may be fluorine, chlorine, bromine, methyl, ethyl, bromomethyl, fluoromethyl, trifluoro- methyl, or nitro, one of X 1 and X2 being fluorine, chlorine, or bromine. In a preferred embodiment, X and X independently will be selected from fluorine, chlorine, and bromine. In a particularly preferred embodiment X will be chlorine or, especially, fluorine 2 and X will be chlorine. It will be understood that any alkyl, alkenyl or alkynyl groups of the compound may be straight chain or branched chain radicals. Thus, 1-methylethyl, 2-methyl- 2-propenyl, and 1-methyl-2-propynyl are branched chain examples of alkyl, alkenyl, and alkynyl radicals respec- tively. The halogen may be fluorine, chlorine, bromine or iodine. The haloalkyl radical may have one or more same or different halogen atoms. In one aspect of the invention, Z is hydrogen and W, R, X 1 , and X 2 are as defined above. Preferably W is oxygen and R is n-propyl or a fluoropropyl radical such as 3-fluoropropyl . X 1 and X 2 are preferably independently selected from fluorine , chlorine , and bromine . More preferably , X is chlorine or , espe- 2 cially, fluorine and X is chlorine. The compounds in which Z is hydrogen are generally less active herbi- cidally than the corresponding compounds in which Z is one of the substituent groups described below. Z may also be selected from fluorine , chlorine , bromine , cyano , nitro , alkyl ( preferably of 1 to 6 carbon atoms) such as methyl , alkyl (preferably of 1 to sA- - iPO 5 carbon atoms) substituted with one or more fluorine, chlorine, or bromine atoms or alkoxy groups of 1 to 4 carbons, and alkynyl (preferably of 3 to 5 carbon atoms) such as 2-propynyl. Examples of substituted alkyl include -CF. and acetal and ketal groups such as -CH(OC 2 H 5 ) 2 and -C(CH 3 ) (OC 2 H 5 ) 2 . W, X 1 , X 2 , and R are as defined above, both generically and otherwise. Z may also be a radical selected from the group consisting of the , and R being as defined above both generically and otherwise. Z is - QR 1 0 is sulfur or, preferably, oxygen and R is alkyl (preferably of 1 to 6, more preferably of 1 to 4, carbon atoms), haloalkyl (preferably of 1 to 5 carbon atoms), particularly a fluoroalkyl, hydroxyalkyl (preferably of 1 to 5, more preferably of 1 to 3, carbon atoms), cyanoalkyl (preferably of 1 to 5 alkyl carbon atoms), alkoxyalkyl (preferably of 2 to 6 carbon atoms), alkyl¬ thioalkyl, alkylsulfinylalkyl, or alkylsulfonylalkyl (each preferably of 2 to 6 carbon atoms), alkanoyl (preferably of 2 to 5 carbon atoms), alkenyl (preferably of 2 to 5, more preferably of 3 to 5, carbon atoms), haloalkenyl (preferably of 2 to 5, more preferably of 3 to 5, carbon atoms) such as a halo-2-propenyl, alkenyl- oxyalkyl (preferably of 3 to 6 carbon atoms), alkynyl (preferably of 2 to 5, more preferably 3 to 5, carbon atoms), haloalkynyl (preferably of 2 to 5, more prefer¬ ably 3 to 5, carbon atoms), alkoxycarbonyl (preferably of 1 to 4 alkyl carbon atoms), or a three- to eight- embered ring heterocyclic group of one or two, same or different (preferably the same), ring heteroatoms selected from oxygen and sulfur or an alkyl radical (preferably of 1 to 4, more preferably 1, carbon atoms) substituted with said heterocyclic group. R is preferably 2-propynyl or 3-halo-2-propynyl such as 3-iodo-2-propynyl or 3-bromo-2-propynyl. When R is a heterocyclic group or an alkyl radical substituted therewith, the heterocyclic group may be saturated, unsaturated, or aromatic, it may be substi¬ tuted with halogen (generally fluorine, chlorine, or bromine), alkyl, (preferably of 1 to 4 carbon atoms), or haloalkyl (preferably of 1 to 4 carbon atoms), and it may be adjoined to a benzene ring at two adjacent ring carbon atoms to form a benzo-heterocycle bicyclic group, for example a 1 ,4-benzodioxanyl group. In sulfur- containing heterocycles, the sulfur may be present in divalent form or as the S-oxide or S-dioxide. In a sub-genus of particular interest, the heterocyclic group is saturated, unsubstituted, of 5 or 6 ring atoms including 1 or 2 same ring heteroatoms (sulfur or oxygen) , and is connected directly to the oxygen moiety of the Z group or indirectly via methylene group. In this sub-genus Z is advantageously 3-tetrahydrofuranyl- oxy or tetrahydrofurfuryloxy. Examples of z groups when Z is -QR and R is other than (and does not contain) a heterocyclic group include such radicals as -0CH 3 , -0C 2 H ς , -0-n-C 3 H-, -OCH(CH 3 ) 2 , -0-n-C 4 H 9 , -OCH 2 CH(CH 3 ) 2 , -SCH 3 , -SCH(CH 3 ) 2 , -OCHF 2 , -SCHF 2 , -OCH 2 CH 2 , -OCH 2 CF 3 , -SCH 2 CF 3 , -0(CH 2 ) 2 CH 2 F, -0CH 2 CH 2 C1, -OCH 2 CH 2 Br, -OCH 2 CH 2 OH, -SCH 2 CH 2 OH, -OCH 2 CN, -SCH 2 CN, -OCH(CH 3 )CN, -OCH(CN)CH(CH 3 ) 2 , -OCH 2 OCH 3 , -OCH 2 OC 2 H 5 , -SCH 2 OCH 3 , -0(CH 2 ) 2 OCH 3 , -OCH(CH 3 )OCH 3 , -0(CH 2 ) 2 OC 2 H 5 , OCO^Hg, -S(CH 2 ) 2 OCH 3 , -OCH(CH 3 )CH 2 OCH 3 , -OCH 2 SCH 3 , -SCH 2 SCH 3 , -OCB. 2 S(0)CH 3 , -OCH(CH 3 )SCH 3 , -OCH(CH 3 )S(0)CH 3 , -OCH(CH 3 )S(0) 2 CH 3 , -0(CH 2 ) 2 OCH=CH 2 , -S(CH 2 ) 2 OCH=CH 2 , -0(CH 2 ) 2 OCH 2 CH=CH 2 , -OCOCH 3 , -SCOCH 3 , -OCOCH(CH 3 ) 2 , -OCH 2 CH=CH 2 , OCH(CH 3 )C=CH 2 , -SCH 2 CH=CH 2 , -OCH 2 C(Cl)=CH 2 , -SCH 2 C(C1)=CH 2 , -OCH 2 CBr=CHBr, -OCH..C3CH, -SCH 2 C=CH, -OCH 2 CsCCH 3 , -OC(CH 3 ) 2 CsCH, -OCH(CH 3 )C=CH, -OCH 2 CsCI, and -OCH„C=CBr. Examples of Z when R 1 is or contains a hetero¬ cyclic group include -O- , -OCH 2 - , -OCH 2 -< ] , " ° " φ , _Q , 0 -CjP _ -0- ) , "OCH,-^ , "S_ .. -S- , -OCH 2 CH.- , -° CH 2 * ^ ) , -0 (CH 2 , 3 _ζ] / _ -_Q, _ C «3 ^ CH 3 •OCH 2 -il 0 !i -OCH 2 -ζ!J -OCH. • OMPI _Z___is__-O_S_O__._R_ 2 R is alkyl (preferably of 1 to 8 carbon atoms), haloalkyl, cyanoalkyl, or arylalkyl wherein each alkyl is preferably of 1 to 5 carbon atoms, cyclic alkyl (preferably of 3 to 8 carbon atoms), alkenyl, halo¬ alkenyl, or arylalkenyl wherein each alkenyl is prefer¬ ably of 2 to 5 carbon atoms, alkynyl, haloalkynyl, or arylalkynyl wherein each alkynyl is preferably of 2 to 5 carbon atoms, aryl such as phenyl, or a group of the formula -(CH__)mNR R 4 or (CH_ 0 )n-Y-R wherein m is 0 to 5 (preferably 0 to 3) and n is 1 to 5 (preferably 1 to 3); R is hydrogen or alkyl (preferably of 1 to 5 carbon atoms); 4 R is alk ■ _yyll i(preferably of 1 to 5 carbon atoms) or a group -CH--Y-R.5; ς - R is alkyl (preferably of 1 to 5 carbon atoms), alkenyl or alkynyl (preferably of 2 to 5, more prefer- ably of 3 to 5, carbon atoms), or a radical -CH(R 18 ) C0 R19; R 18 and R19 are independently hydrogen or alkyl (preferably of 1 to 4 carbon atoms); and Y is oxygen or S(O) in which r is 0 to 2. A number of interesting compounds within the above 2 subgenus comprise the series wherein R is alkyl of 1 to 8 carbon atoms, haloalkyl, cyanoalkyl, or arylalkyl wherein each alkyl is of 1 to 5 carbon atoms, cyclic alkyl of 3 to 8 carbon atoms, alkenyl or haloalkenyl of 3 to 5 carbon atoms, alkynyl or haloalkynyl of 3 to 5 carbon atoms, or a group (CH,) NR R or (CH_) -γ-R wherein m is 0 to 3, n is 1 to 3, and R and R are independently alkyl of 1 to 5 carbon atoms. 2 Frequently, R will be alkyl of 1 to 5 carbon atoms, especially methyl; haloalkyl of 1 to 3 carbon atoms having one or more fluorine, chlorine, or bromine atoms; cyanoalkyl or phenylalkyl of 1 to 3 alkyl carbon atoms; cyclic alkyl of 3 to 6 carbon atoms; alkenyl or alkynyl of 3 to 5 carbon atoms; haloalkenyl of 3 to 5 carbon atoms such as a halopropenyl, for example, a halo-2- propenyl having one or more halogen atoms such as chlorine; haloalkynyl of 3 to 5 carbon atoms, espe- cially a 3-halo-2-propynyl, a group of the formula (CH,) N(R 3 ) 2 in which m is 0 or 2 and R 3 is alkyl of 1 to 5 carbon atoms such as methyl; or a group of the formula (CH,) -Y-R 5 in which n is 1 or 2, espe- cially 2, Y is oxygen or sulfur, and R is alkyl of 1 to 5 carbon atoms such as methyl or ethyl, alkenyl or alkynyl of 3 to 5 carbon atoms, or a radical -CH(R 18)CO,R19 in which R 18 is hydrogen or methyl and R19 is alkyl of 1 to 4 carbon atoms such as methyl or ethyl. 2 Examples of specific R groups include CH 3 , C 2 H 5 , n-C 3 H ? , CH(CH 3 ) 2 , n-C^, CH 2 CH(CH 3 ) 2 , CH(CH 3 )CH 2 CH 3 , (CH 2 ) 2 CH(CH 3 ) 2 , CF 3 , CHF 2 , CH j Cl, CHCl j , CH 2 Br, (CH 2 ) 2 CH 2 C1, CH 2 CN, CH j CgH^ CHCH j CH^ CH=CH 2 , CH 2 CH=CH 2 , CH 2 C(C1)=CC1 2 , CH=CHC g H 5 , CH 2 C=CH, CH 2 C=CI, CgH 5 , NHCH 3 , N(CH 3 ) 2 , (CH 2 ) 2 N(CH 3 ) 2 , (CH 2 ) 2 OCH 3 , (CH 2 ) 2 OCH 2 CH 3 , (CH 2 ) 2 OCH 2 CH=CH 2 , (CH 2 ) 2 SCH 2 CH=CH 2 , (CH 2 ) 2 OCH 2 C=CH, (CH 2 ) 2 OCH 2 C0 2 CH 3 , and (CH 2 ) 2 SCH 2 C0 2 CH 3 . Z is -Q-R 7 -CO-Q 1 R 8 Q and Q are independently oxygen or sulfur. R is an alkylene or haloalkylene (such as fluoro- alkylene) radical, preferably of 1 to 3 carbon atoms, for example, -CH 2 ~, -CH(CH 3 )-, or -CHF-. R is hydrogen, alkyl or substituted alkyl (pre- ferably of 1 to 8 carbon atoms), alkenyl or alkynyl (preferably of 2 to 5, more preferably 3 to 5, carbon atoms) , for example, 2-propenyl, 1-methyl-2-propenyl, or 2-propynyl, or a monovalent cyclic group of 3 to 7 ring atoms which may be an aromatic (such as phenyl), hetero- cyclic (such as 3-tetrahydrofuranyl, 2-oxo-3-tetrahydro- furanyl, 3-tetrahydrothienyl or the oxide or dioxide thereof, or 3-pyridyl), or alicyclic (such as cyclo- propyl, cyclopentyl, or cyclohexyl) radical, the valence being on a carbon atom of said cyclic group, or an alkyl radical of 1 to 3 (preferably 1 ) carbon atoms substi¬ tuted with said cyclic group, for example, cyclopropyl- methyl, tetrahydrofurfuryl, furfuryl, thenyl, or benzyl. When R 8 is substituted alkyl, the alkyl substi- tuent(s) will frequently be selected from nitro, halo (such as chloro, bromo, or, particularly, fluoro), cyano, alkoxy or alkyl(thio, sulfinyl, or sulfonyl) of 1 to 4 alkyl carbon atoms, phenyl(thio, sulfinyl, or sulfonyl), alkylamino or dialkylamino in which each alkyl independently is preferably of 1 to 4 carbon atoms, aminocarbonyl, or alkylaminocarbonyl or dialkyl- a inocarbonyl in which each alkyl independently is preferably of 1 to 4 carbon atoms. Thus, in this aspect of the invention, Z may be -OR 7 C0 2 R 8 , -SR 7 -CO-SR 8 , -OR 7 -CO-SR 8 , or -SR 7 C0 2 8 . In a narrower aspect of the invention Q is oxygen or sulfur (frequently oxygen), Q is oxygen, R is -CH,- or -CH(CH 3 )-, and R 8 is hydrogen, alkyl, haloalkyl (particularly a fluoroalkyl), cyanoalkyl, alkoxyalkyl, cyclic alkyl such as cyclopentyl, (cyclic alkyl)alkyl such as cyclopropylmethyl, or alkynyl. Examples of Z groups when Z is -Q-R 7-CO-Q1R8 in- elude OCH 2 C0 2 H, OCH 2 C0 2 C 2 H 5 , SCH 2 C0 2 H, SCH 2 -CO-SCH 3 , -OCH(CH 3 )C0 2 C 2 H 5 , OCH(CH 3 )C0 2 CH(CH 3 ) 2 , OCH(CH 3 )C0 2 C(CH 3 ) 3 , OCH(CH 3 )CO j CH(CH 2 CH 3 ) 2 , 0CH(CH 3 )C0 2 CH(CH 3 )CH(CH 3 ) 2 , OCH(CH 3 )C0 2 CH[CH(CH 3 ) 2 ] 2 , OCH(CH 3 )C0 2 CH(CH 3 )CH 2 CH 3 , OCH(CH 3 )C0 2 CH(CH 2 ) 3 CH 2 , 0CH(CH 3 )C0 2 H,. SCH(CH 3 )C0 2 H(CH 3 ) 2 , 0CH(CH 3 )C0 2 CH 2 CHCH 2 CH 2 , SCH(CH 3 )C0 2 H, 0CH(CH 3 )C0 2 C(CN)(CH 3 ) 2 , 0CH(CH 3 )C0 2 CH(CH 2 0CH 3 ) 2 , OCH(CH 3 )C0 2 CH(CH 3 )C=CH, OCH(CH 3 )C0 2 C(CH 3 ) 2 C=CH, OCH(CH 3 )C0 2 CH 2 CH 2 F, 0CH(CH 3 )C0 2 CH 2 CF 3 , OCH(CH 3 )C0 2 CH(CH 2 F) 2 , 0CHFC0 2 H, SCHFC0 2 H, OCHFC0 2 CH 3 , OCH 2 CO-SC 2 H 5 , OCH(CH 3 )-CO-SC 2 H 5 , -OCH(CH 3 )C0 2 CH 2 CH=CH 2 , -SCH(CH 3 )C0 2 CH 2 CH=CH 2 , -OCH 2 C0 2 C 6 H 5' °CH ( CH 3 )C0 2 -τ j OCH(CH-)CO, 7 OCH(CH 3 )C0 2 CH 2 CgH 5 , OCH(CH 3 )C0 2 CH 2 r^ OCH(CH 3 )C0 2 CH 2 CH 2 CH 3 ) 2 , OCH(CH 3 )C0 2 CH 2 CON(C 2 H 5 ) 2 , -SCH(CH 3 )C0 2 CH 2 OCH 3 , OCH(CH 3 )C0 2 CH 2 SCH 3 , OCH(CH )C0 2 CH 2 SOCH 3 , OCH(CH 3 )C0 2 CH 2 S0 2 CH 3 , OCH(CH 3 )C0 2 CH 2 CONH 2 , OCH(CH 3 )C0 2 CH 2 CH(N0 2 )CH 3 , OCH(CH 3 )C0 2 CH 2 CN, and OCH(CH 3 )C0 2 CH 2 SC g H 5 . The free acids (Z is -QR CO.H) may be converted into their salts such as their sodium, potassium, calcium, ammonium, magnesium, or mono-, di-, or tri(C. to C. alkyl)ammonium salts which may also be used as herbicides. Z is -Q-R 7 -CQ -N * -C(R 9 ) (R 10 ) Q and R are as defined above. One of R 9 and R 10 is alkyl and the other is alkyl or alkylthio, each alkyl (independently) prefer¬ ably being of 1 to 4 carbon atoms. Examples of Z include OCH(CH 3 )C0 2 N=C(CH 3 ) 2 , SCH 2 C0 2 N=C(CH 3 ) 2 , OCHFC0 2 N=C(SCH 3 ) (CH 3 ) , OCH(CH 3 )C0 2 N=C(SCH 3 ) (CH 3 ), OCH(CH 3 )C0 2 N=C(CH 3 ) (C^) , and OCH 2 C0 2 N=C(CH 3 ) 2 . Z is -Q-R 7 -C(CH 3 )=R 11 ) Q and R are as defined above. «11 is oxygen or N-OR 20 in which R ,20 is hydrogen or alkyl (preferably of 1 to 4 carbon atoms). Examples of Z substituents for this sub-genus include 0CH(CH 3 )C(CH 3 )=N-OH, SCH(CH 3 )C(CH 3 )=N-OH, OCH 2 C(CH 3 )=N-OH, OCHFC(CH 3 )=N-OH, SCH(CH 3 )C(CH 3 )=N-OCH 3 , OCH(CH 3 )C(CH 3 )=-N-OCH(CH 3 ) 2 , OCH(CH 3 )C0CH 3 , SCH(CH 3 )COCH 3 , OCHFCOCH 3 , OCH 2 COCH 3 , and SCH 2 COCH 3 . Z is -Q-R 7 -CO-N(R 12 )(R 13 ) Q and R7as defined above. N(R 12 )(R 13 ) is NH 2 or the residue of a primary or secondary amine or of a sulfonamide. For example, one of R 12 and R13 may be hydrogen, alkyl (preferably of 1 to 4 carbon atoms), or alkenyl (preferably of 3 to 5 carbon atoms) such as 2-propenyl, and the other may be hydrogen, alkyl (preferably of 1 to 4 carbon atoms), cyanoalkyl (preferably of 1 to 4 alkyl carbon atoms), alkoxyalkyl (preferably of 2 to 4 carbon atoms), alkenyl (preferably of 3 to 5 carbon atoms) such as 2-propenyl, alkynyl (preferably of 3 to 5 carbon atoms) such as 2-propynyl, alkylsulfonyl (preferably of 1 to 4 carbon atoms), arylsulfonyl in which aryl is unsubstituted phenyl or phenyl substituted with halogen (such as fluorine or chlorine) or alkyl (preferably of 1 to 4 - carbon atoms such as methyl), haloalkylsulfonyl (pre¬ ferably of 1 to 4 carbon atoms), for example, a fluoro- alkylsulfonyl such as trifluoromethylsulfonyl, alkyl- • aminosulfonyl or dialkylaminosulfonyl in which each alkyl independently is preferably of 1 to 4 carbon atoms, or CH(H or CH,)CC,alkyl in which alkyl is 12 13 preferably of 1 to 4 carbon atoms. R and R may also be taken together and with the nitrogen atom forma 5- or 6-membered heterocyclic ring which may contain an oxygen atom in the ring, for example, N(R 12)(R13) may be a pyrrolidino, piperidino, or morpholino ring. In one aspect of this embodiment, R 12 and R13 will be the same or will be taken together to form a hetero- 12 13 cyclic ring. In another aspect one of R and R will be alkyl or, frequently, hydrogen and will be different from the other. Examples of Z substituents for this embodiment include OCH(CH 3 )CONH 2 , OCH(CH 3 )CON(CH 3 ) 2 , OCH(CH 3 )CON(CH 2 CH=CH 2 ) 2 , OCH(CH 3 )CONHSO^gH-., OCH(CH 3 )CONHS0 2 -C 8 H 4 (2-C1) , OCH(CH 3 )CONHS0 2 -CgH 4 (4-Cl) , OCH 2 CON(CH 3 ) (C 2 H 5 ) , OCH(CH 3 )CONHCH(CH 3 ) 2 , OCHFCONHS0 2 -n-C 3 H 7 , OCH(CH 3 )CONHCH 2 CsCH, OCH(CH 3 )CO HCH 2 C0 2 CH 3 , OCH(CH 3 )CO HS0 2 -CgH 4 (4-CH 3 ) , OCH(CH 3 )CONHC(CH 3 ) 2 C=CH, OCH(CH )CONHC(CH 3 ) 2 CN, OCH(CH 3 )CONHS0 2 CF 3 , OCH(CH 3 )CONHS0 2 HCH 3 , OCH(CH 3 )CONHS0 2 N(CH 3 ) 2 , OCH(CH 3 )CONHCH 2 CH 2 OCH 3 , ' OCH 2 CONH 2 , OCHFCONHCH 3 , OCH(CH 3 )CONHCH(CH 3 )C0 2 C 2 H 5 , SCH(CH 3 )CON(CH 3 ) , SCH(CH 3 )CONHCH 2 CH=CH 2 , OCH(CHj,)CONI(CH_-_)4.CtH,_;, OCH(CH i,)CONr(CH, tt) i,CiH_-, " OCH(CH 3 )CON(CH 2 ) 2 OCH 2 CH 2 , and SCH 2 CONHS0 2 CF 3 . Z is N(R 14 ) (R 15 ) R 14 and R15 are independently selected from hydro¬ gen, alkyl (preferably of 1 to 4 carbon atoms), alkenyl or alkynyl (preferably of 3 to 5 carbon atoms), cyano- alkyl (preferably of 1 to 4 alkyl carbon atoms), acetyl, alkoxycarbonyl (preferably of 1 to 4 alkyl carbon atoms), alkoxyalkyl (preferably of 2 to 4 carbon atoms), • aminocarbonyl, alkylaminocarbonyl or dialkylaminocar- bonyl in which each alkyl is preferably of 1 to 4 carbon atoms, alkylsulfonyl (preferably of 1 to 4 carbon atoms), haloalkylsulfonyl (preferably of 1 to 4 carbon atoms), for example, a fluoroalkylsulfonyl such as trifluoromethylsulfonyl, arylsulfonyl in which aryl is unsubstituted phenyl or phenyl substituted with halogen (such as fluorine or chlorine) or alkyl (preferably of 1 to 4 carbon atoms such as methyl), and CH(H or CH,)C0 - alkyl in which alkyl is preferably of 1 to 4 carbon atoms, or N(R 14 )(R 15 ) is a group N=C(R 9 )(R ) in which one of R 9 and R is alkyl and the other is hydrogen, alkyl, or alkylthio, each alkyl (independently) prefer- 14 15 5 ably being of 1 to 4 carbon atoms. N(R )(R ) may also represent a cyclic group such as tetrahydrophthalimido or 2-oxopyrrolidino. Examples of Z groups for this embodiment include NHCON(CH 3 ) 2 , NHCONH 2 , NHCONHCH 2 CH(CH 3 ) 2 , NHCONHCH 3 , 10 NH 2 , N(CH 3 ) 2 , NHCH 3 , N(C 2 H 5 ) 2 , NHCH 2 CH=CH 2 , NHCH 2 C=CH, N(CH 2 CN)COCH 3 , N(C 2 H 5 )COCH 3 , NHCOCH 3 , NHCH 2 CG 2 C 2 H 5 , NHC0 2 CH 3 , NHCH(CH 3 )C0 2 C 2 H 5 , NHCH 2 CH 2 OCH 3 , NHS0 2 CH 3 , N(CH 3 )S0 2 CH 3 , N(C 2 H 5 )S0 2 CH 3 , N(S0 2 CH 3 ) 2 , NHS0 2 CF 3 , N(S0 2 CF 3 ) 2 , NHS0 2 CgH 5 , NHS0 2 -CgH 4 (4-C1) , 15 NHS0 2 -CgH 4 (4-CH 3 ), =C(CH 3 ) 2 , N=CHCH 3 , N=C(CH 3 ) (C j Hg) , N=C(SCH 3 ) (CH 3 ) , * is 16 - S ° 2 20 R 16 is hydro y, amino, alkylamino or dialkyl- amino in which each alkyl is preferably of 1 to 4 carbon atoms, or arylamino in which aryl is unsubstituted phenyl or phenyl substituted with halogen (such as 25 fluorine or chlorine) or alkyl (preferably of 1 to 4 carbon atoms such as methyl). Examples of Z groups for this embodiment include • S0 3 H- S0 2 NH 2 , S0 2 NHCH 3 , S0 2 N(C 2 H 5 ) 2 , S0 2 N(CH 3 ) (C^) , S0 2 NHCH(CH 3 ) 2 , S0 2 NHC g H 5 , S0 2 NHCgH 4 (4-C1) , and 30. S0 2 NHC g H 4 (4-CH 3 ). Z is CO-R 17 R 17 is hydroxy, alkoxy or alkylthio (preferably 5 of 1 to 4 carbon atoms), amino, alkylamino or dialkyl- amino in which each alkyl is preferably of 1 to 4 carbon O PI atoms, or arylamino in which aryl is unsubstituted phenyl or phenyl substituted with halogen (such as fluorine or chlorine) or alkyl (preferably of 1 to 4 carbon atoms such as methyl). Acid salts (same as above) are also useful. Examples of Z groups for this embodiment include C0 2 H, C0 2 CH 3 , C0 2 CH(CH 3 ) 2 , CO-SCH 3 , CONH- CONHCH- C0N(C 2 H 5 ) 2 , C0N(CH 3 ) (C 2 H 5 ) , C0NHCH(CH 3 ) 2 , CONHCgH^ C0NHC g H 4 (4-C1) , and C0NHC g H 4 (4-CH 3 ). For each of the Z substituents described above, a preferred embodiment comprises the compounds in which W is oxygen, R is n-propyl or, particularly, a fluoro- propyl such as 3-fluoropropyl, X is chlorine or, 2 especially, fluorine, and X is chlorine. The com- pounds in which z is OR have very high herbicidal activity, especially where R is 2-propynyl (or a 3-halo-2-propynyl such as 3-iodo- or bromo-2-propynyl) . Any free acid compound of formula I may be con¬ verted into a salt such as a sodium, potassium, calcium, ammonium, magnesium, or mono-, di- or tri(C. to C. alkyl)ammonium salt which may also be used as an herbi¬ cide. Many of the present herbicidal compounds may be prepared by the methods illustrated in the chemical equations below. IVa Treatment of an appropriately substituted phenylamine, II, with trichloromethyl chloroformate gives the corre¬ sponding isocyanate Ilia, which upon treatment with trimethylsilyl azide in the manner of 0. Tsuge et al., ______ Qr9» Chem. , 45, 5130 (1980), incorporated herein by reference, affords the intermediate tetrazolinone IVa. Intermediate IVa may also be prepared by treatment of the isocyanate Ilia with aluminum azide in the manner of J. Horwitz et al. , J^ Am. Chem. Soc. , 8__, 3076 (1959), incorporated herein by reference. Treatment of the N-4 unsubstituted tetrazolinone IVa with R-Y, wherein Y is a good leaving group, in the presence of a base gives compound la. The leaving group Y will generally be a chlorine, bromine, or iodine atom, but may be any readily displaceable group used in the art in similar reactions. The use of sodium hydride base in di ethyl- formamide has been found to give satisfactory results. This method is generally useful where compound II is readily available, either commercially or by prepara- tion, and is particularly useful where Z is hydrogen, halogen, cyano alkyl, substituted alkyl, or -OR wherein R is alkyl, especially lower alkyl such as methyl, or benzyl (a useful intermediate discussed below) . The corresponding thiones lb (I, W is sulfur) may be prepared in a similar manner by treating the appro¬ priately substituted phenylamine II with thiophosgene in the presence of triethylamine to give corresponding isothiocyanate (Illb) and treating that first with sodium azide and water, then with acid (e.g. HC1/H,0) to give the thione (IVb) which may be concerted by reaction with R-Y (as above for IVa) to the thione (lb). In some instances the desired Z group may be unstable under the conditions used in preparing II or in converting II into I. In such cases or where it is otherwise not desirable or convenient to proceed by the methods outlined above, it may be advantageous to add OMPI the desired Z substituent to the molecule subsequent to the addition of the desired R group (or a group that can be subsequently converted into the desired R group) . In such cases a useful and versatile intermediate is com- pound I in which Z is -QH (the 5-hydroxyphenyl compound, V, or the corresponding 5-mercaptophenyl compound, VI). Compound V (Z is OH) is readily prepared from the corresponding compound I in which Z is a lower alkoxy group or a benzyloxy group by treatment with an acidic reagent such as concentrated sulfuric acid, concen¬ trated hydrobromic acid, or a mixture of hydrobromic and acetic acids to effect dealkylation, or, where Z is benzyloxy, by hydrogenolysis over palladium on charcoal (H 2 /Pd/C/C 2 H 5 OH). _dealkylation I(Z=0-Alkyl or CO^CgHg) v . The 5-mercaptophenyl compound (VI) may be prepared from the corresponding compound in which Z is hydrogen by the following sequence of steps: nitration (e.g. H 0 3 /H 2 S0 4 ) to give the corresponding 5-NO, compound (I, Z is N0 2 ), reduction (e.g. H 2 T0 2 /C 2 H 5 OH) to give the corresponding 5-NH 2 compound (I, Z is NH 2 ), treat- • ment first with NaN0 2 /HCl then with S0 2 /CuCl to give the corresponding 5-S0 2 Cl compound (I, Z is S0 2 C1), and, finally, reduction (e.g. Sn/HCl) to give the 5-SH compound VI (I, Z is SH). I (Z-H) VI The appropriate compound V (I, Z = OH) or compound VI (I, Z - SH) is then treated in the presence of a base with the appropriate Y-R 1 , Y-S0 2 R2, Y-R 7 -C0-QR 8 (R 8 H) , Y-R 7 -C0 2 -N=C(R 9 ) (R 1 °) , or Y-R 7 -C(CH,)-R 11 , wherein Y is a good leaving group, • -* ■ 1 2 to give compound I in which Z is -QR , -OS0 2 R , -QR ? CO-QR 8 (R 8 H), -QR 7 CO,N=C(R 9 ) (R 10 ) , or 7 11 -QR C(CH 3 )=R . Alternatively, compounds of formula I in which Z is -QR 7 -C0-SR 8 or -QR 7 C0,N=C(R 9 ) (R 1 °) may be prepared from the corresponding compound in which Z is -QR 7C0,R8 Similarly, compounds of formula I in which -Z is -QR 7CON{R12)(R13) may be prepared from the corre- sponding compound in which Z is -QR COCl (prepared as described above) by treatment HN(R 12)(R13). An alternative method for preparing the compounds of formula I in which Z is -QR C(CH,)=R wherein R is N-OR 20 is by reacting the corresponding compound in which R is oxygen (prepared as described above) with H 2 N-OR 20 . In the conversion of V or VI into I described • above, the base and the leaving group Y may be selected from those used in the art for similar reactions. The 2 leaving group Y in R S0 2 Y will usually be chlorine or bromine. Examples of suitable bases for the reaction 2 with R S0,Y are sodium hydride and triethyla ine. For R 1-Y, Y will generally be chlorine, bromine, iodine, or 4-methylphenylsulfonyloxy. Suitable bases include sodium hydride and, where Y is bromine, chlorine, or iodine, potassium carbonate and potassium fluoride. Compound I in which Z is S0 2 R 6 may be prepared from the corresponding compound in which Z is SO Cl (prepared as described above) by treatment with water (R 1 fi is hydroxy), ammonia (R16 is NH,) or an appro- priate amine (R 16 is alkylamino, dialkylamino, or arylamino) . Compounds of formula I in which Z is cyano (which may be prepared as described above from II) are useful intermediates for the corresponding compounds in which Z 17 iiss --CCOO--RR 17 bbyy hhyyddrroollyyssiiss ffoolllloowweedd by estπfication or amide formation as the case may be. Compounds of formula I in which Z is -N(R 14)(R15) may be prepared by reduction of the corresponding nitro compound (Z=NO,, prepared as described above) to give the amino derivative (Z=NH,, discussed above) followed by appropriate alkylation, acylation, or sulfonylation as the case may be. The amino compound may also be converted into the corresponding isocyanate (Z=NC0) by treatment with trichloromethyl chloroformate. Treatment of the isocyanate (Z=NC0) with an appropriate amine gives the corresponding compound in which Z is -N(R 14) (R15 and one of R 14 and R15 is hydrogen and the other is aminocarbonyl, alkylaminocarbonyl or dialkylaminocar- bonyl. The amino compound (Z=NH,) may also be used to prepare the compounds in which N(R 14)(R15} is the group N=C(R 9 )(R 10 ) (by treatment with R 9 R 10 C=0) or a cyclic group such as a tetrahydrophthalimido (by treatment with tetrahydrophthalic anhydride). Compounds of formula I in which Z and X are 2 halogen atoms and X is nitro may be prepared by nitration (e.g. HN0 3 /H 2 S0 4 ) of the corresponding com¬ pound in which X is hydrogen (e.g. compound 226 in the tables is converted by nitration to compound 217). The Z halogen in the nitro compounds (Z and X are 2 halogen, X is nitro) may be readily displaced to produce other herbicidal compounds of the invention, for example, by reaction with R -OH in the presence of a base (e.g. NaH) to give the corresponding compound in which Z is -OR . Certain of the present compounds may be prepared from intermediate V by the method illustrated in the following chemical equation. 10 The moiety R6CH 2 represents appropria I t C e R1 substi- tuents. The reaction is conducted in the presence of a dehydration reagent such as dicyclohexylcarbodiimide (DCC). 15 Where R is a saturated oxygen- or sulfur-con¬ taining heterocycle, a further method of preparation involves addition of the hydroxy group of V or the ercapto group of VI across the double bond of a dihy- droheterocycle as shown " in the equation below for The compounds in which R is a difluoroalkyl radical in which both fluorine atoms are on the same carbon atom such as -(CH 2 ),CHF 2 or -CH 2 CF 2 CH 3 may be pre- 3.0 pared from the corresponding aldehyde or ketone (e.g. -CH 2 CH 2 CHO or -CH 2 COCH 3 ) by treatment with diethyl- aminosulfur trifluoride (ET 2 N-SF 3 , "DAST") in the pre¬ sence of methylene chloride. The methods described above and in the examples 35 for preparing compound I, and intermediates therefor, comprise a further aspect of the present invention. An additional aspect of the invention pertains to O PI the intermediates themselves, particularly compounds IV, V, VI, and VII. With respect to compound IV, W is sulfur or, preferably, oxygen, one of X 1 and X2 is fluorine, chlorine, or bromine and the other is fluorine, chlo¬ rine, bromine, alkyl (preferably of 1 to 6 carbon atoms, more preferably of 1 to 4, carbon atoms) such as methyl, or haloalkyl (preferably of 1 to 5 carbon atoms) parti- cularly fluoromethyl, trifluoromethyl, or bromomethyl, (or X 2 may be N0 2 when X1 is F, Cl, or Br) , and Z is hydrogen, fluorine, chlorine, bromine, cyano, nitro, alkyl (preferably of 1 to 6 carbon atoms) such as methyl, haloalkyl (preferably of 1 to 5 carbon atoms) such as trifluoromethyl, alkynyl (preferably of 3 to 5 carbon atoms), or QR in which Q is sulfur or, prefer¬ ably, oxygen and R is alkyl (preferably of 1 to 6, more preferably of 1 to 4, carbon atoms), haloalkyl (preferably of 1 to 5 carbon atoms), particularly a fluoroalkyl, cyanoalkyl (preferably of 1 to 5 alkyl carbon atoms), alkoxyalkyl (preferably of 2 to 6 carbon atoms), alkylthioalkyl, alkylsulfinylalkyl, or alkyl- • sulfonylalkyl (each preferably of 2 to 6 carbon atoms), alkenyl (preferably of 2 to 5, more preferably of 3 to 5, carbon atoms), haloalkenyl (preferably of 2 to 5, more preferably of 3 to 5, carbon atoms) such as .a halo-2-propenyl, alkenyloxyalkyl (preferably of 3 to 6 carbon atoms), alkynyl (preferably of 2 to 5, more preferably 3 to 5, carbon atoms) or haloalkynyl (pre- ferably of 2 to 5, more preferably 3 to 5, carbon atoms). R is advantageously benzyl or lower alkyl. With respect to compounds V, VI, and VII, W, X , 2 and X are as defined above for compound IV and R is alkyl (preferably of 1 to 6 carbon atoms), fluoroalkyl (preferably of 1 to 5 carbon atoms), alkoxy¬ alkyl (preferably of 2 to 6 carbon atoms), alkylthio- alkyl (preferably of 2 to 6 carbon atoms), cyanoalkyl (preferably of 1 to 5 alkyl carbon atoms), haloalkoxy¬ alkyl (preferably of 2 to 6 carbon atoms), trifluoro¬ methylthio, alkenyl (preferably of 2 to 5 carbon atoms), 2-oxopropyl, 3-oxopropyl, or haloalkenyl (preferably of 2 to 5 carbon atoms). Preferably R is n-C 3 H 7 or, particularly, a fluoroalkyl such as 3-fluoropropyl. Representative compounds of the invention are shown in Table 1. Characterizing data for many of the compounds are given in Table 2. The preparation and herbicidal activity of repre¬ sentative compounds of this invention are illustrated further in the examples below. All temperatures are in degrees Celsius, and all pressures are in mm Hg. Example 1 1 ,4-DIHYDRO-4-PROPYL-1-(2,4,5-TRICHLOROPHENYL)- 5H-TETRAZOL-5-ONE Step A: 1 ,4-Dihydro-1-( 2,4 ,5-trichlorophenyl )- 5H-tetrazol-5-one In a manner similar to that disclosed by Tsuge et al., J. Org. Chem., 45, 5230 (1980), the reaction of 6.2 g (0.028 mole) of 2,4,5-trichlorophenyl isocyanate and 6.4 g (0.056 mole) of trimethylsilyl azide produced 1 ,4-dihydro-1-(2,4,5-trichlorophenyl)-5H-tetrazol-5-one as a solid, 175-176 β C. The nmr and ir spectra were consistent with the proposed structure. Analysis calc'd for C 7 H 3 C1 3 N 4 0: C 31.66; H 1.14; N 21.10; Found: C 34.78; H 1.62; N 18.02. Step B: 1 ,4-Dihydro-4-propyl-1-(2,4,5-trichloro- phenyl)-5H-tetrazol-5-one To a stirred mixture of 0.24 g (0.005 mole) of sodium hydride (60% oil suspension) in 45 mL of N,N- di ethylforma ide was added 1.3 g (0.005 mole) of 1 ,4-dihydro-1-(2,4,5-trichlorophenyl)-5H-tetrazol-5- one. The mixture was stirred at room temperature for 15 minutes, then 0.85 g (0.005 mole) of 1-iodopropane and several drops of 1 ,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) were added. After complete addition, the reaction mixture was stirred at room temperature for 4 days. The reaction mixture was poured into ice water and the resulting mixture extracted with diethyl ether. The ether extract was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to leave a solid. The solid was puri¬ fied by column chromatography on silica gel, eluting with methylene chloride. Recrystallization from ethanol -gave Q.3 g of 1 ,4-dihydro-4-propyl-1-(2,4,5-trichloro- phenyl)-5H-tetrazol-5-one as a solid, p 89-90'C. The nmr and ir spectra were consistent with the proposed structure. The tetrazolinone of Example 1 is listed in Table 1 as compound 1. Compounds 2, 3 and 109-114 were prepared by an analagous method. Example 2 1-(2 ,4-DICHL0R0-5-METHYLPHENYL)-1 ,4-DIHYDR0- 4-PROPYL-5H-TETRAZOL-5-ONE Step A: 3-Acetamidotoluene Acetic anhydride (176 mL) was added slowly to a stirred mixture of 103.2 mL of m-toluidine in 300 mL of water. After complete addition, the mixture was stirred for 4 hours at room temperature. The mixture was cooled in an ice bath, then extracted with diethyl ether. The ether extract was dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated under reduced pressure to leave an oily residue which solidified. The solid was collected, washed with water, then dis¬ solved in diethyl ether. The etheral solution was dried over anhydrous sodium sulfate, filtered, and the fil¬ trate evaporated under reduced pressure to yield 3- aσetamidotol ene as a solid, mp 59-61 β C. Step B: 2,4-Dichloro-5-methylacetanilide Sulfuryl chloride (120 mL) was added dropwise to 75.0 g (0.05 mole) of 3-acetamidotoluene with stirring. After complete addition, the reaction mixture became solid and was allowed to stand at room temperature for approximately 60 hours. The solid mixture was heated until a slurry formed, then stirred for approximately 5 hours. The mixture was cooled to room temperature and treated with ice water and methylene chloride. The resulting two-phase mixture was filtered, and the organic phase was separated, dried over anhydrous sodium sulfate, then filtered. The solvent was evaporated from the filtrate under reduced pressure to leave a solid. The solid was purified by recrystallization from ethyl acetate to yield 10.5 g of 2,4-dichloro-5-methylacet- anilide, mp 133-135°C. Step C: 2,4-Dichloro-5-methylaniline A solution of 3.7 g (0.09 mole) of sodium hydroxide in 96 mL of water was added to a stirred suspension of 9.0 g (0.0041 mole) of 2,4-dichloro-5-methylacetanilide in 96 mL of ethanol. After complete addition, the reaction mixture was heated at reflux for 2 hours. The reaction mixture was cooled, diluted with 200 mL of water, and the resultant mixture stirred at room temper- - ature for approximately 60 hours. A precipitate had formed and was collected by filtration and purified by recrystallization from ethyl acetate to yield 4.0 g of 2,4-dichloro-5-methylaniline. Step D: 2,4-Dichloro-5-methylphenyl isocyanate In a manner similar to Kurita, et al. , J. Org. Chem. , 41 , 2070 (1976), incorporated herein by refer- ence, the reaction of 3.43 g (0.0156 mole) of 2,4- dichloro-5-methylaniline and 3.5 g (0.018 mole) of trichloromethyl chloroformate in 50 mL of toluene produced 3.4 g of 2,4-dichloro-5-methylphenyl iso¬ cyanate. Step E: 1-(2,4-Dichloro-5-methylphenyl)-1 ,4-di- hydro-5H-tetrazol-5-one In the manner of Example 1 , Step A, the reaction of 3.4 g (0.016 mole) of 2,4-dichloro-5-methylphenyl isocyanate and 3.6 g (0.031 mole) of trimethylsilyl azide produced 1.07 g of 1-(2,4-dichloro-5-methyl- phenyl)-1 ,4-dihydro-5H-tetrazol-5-one as a solid, mp 135-137 β C. The nmr and ir spectra were consistent with the proposed structure. Step F: 1-(2,4-Dichloro-5-methylphenyl)-1 ,4-di- hydro-4-propyl-5H-tetrazol-5-one Under a dry nitrogen atmosphere, 0.06 g (0.0012 mole) of sodium hydride (50% oil suspension) was washed with petroleum ether to remove the oil, then suspended in 5 mL of anhydrous N,N-diπιethylformamide. To the suspension was added 0.3 g (0.0012 mole) of 1-(2,4-di- chloro-5-methylphenyl)- ,4-dihydro-4H-tetrazol-5-one. After complete addition, the mixture was stirred at room temperature for 30 minutes then heated at 60 β C for 15 minutes. The mixture was cooled to room temperature and 0.4 g (0.0024 mole) of 1-iodopropane added. The resul¬ tant mixture was stirred at room temperature for approx¬ imately 60 hours then poured into ice water. The mixture was extracted with ethyl acetate and the organic phase washed with a saturated aqueous solution of sodium chloride. The organic phase was dried over • anhydrous sodium sulfate, filtered, and the filtrate evaporated to leave an oil. The oil was purified by column chromatography on silica gel, eluting with ethyl acetate:n-hexane (15:85), to yield 0.12 g of 1-(2,4- dichloro-5-methylphenyl)-1 ,4-dihydro-4-propyl-5H-tetra- zol-5-one as a solid, mp 47-48 β C. The nmr and ir spectra were cons istent with the proposed structure. The tetrazolinone prepared in Example 2 is listed as compound 4 in Table 1 . Compounds 5 and 90 were 5 prepared by a similar method starting from the appro¬ priately substituted aniline. Example 3 1 - ( 2 , 4-D ICHLORO-5-METHOXYPHENYL ) - 1 , 4-DIHYDRO- 4-METHYL-5H-TETRAZOL-5-ONE 10 Step A: 3-Hydroxyacetanilide In the manner of Example 2, Step A, the reaction of 66.0 g (0.60 mole) of 3-aminophenol and 77.8 g (0.76 mole) of acetic anhydride in 180 mL of water gave 81.0 g of 3-hydroxyacetanilide as a solid, mp 144-146 β C. The 15 reaction was repeated to obtain an additional quantity of product. Step B: 2,4-Dichloro-5-hydroxyacetanilide In the manner of Example 2, Step B, the chlorina- tion of 100.0 g (0.66 mole) of 3-hydroxyacetanilide with 20 179.8 g (1.33 mole) of sulfuryl chloride in 1570 mL of glacial acetic acid produced 63.5 g of 2,4-dichloro-5- hydroxyacetanilide as a solid, mp 224-226 β C. Step C: 2,4-Dichloro-5-methoxyacetanilide A stirred mixture of 35.0 g (0.16 mole) of 2,4-di- 25 chloro-5-hydroxyacetanilide, 33.1 g (0.24 mole) of potassium carbonate, and 34.1 g (0.24 mole) of methyl iodide in 300 mL of acetone was heated at reflux for approximately 18 hours. The mixture was cooled and filtered. The filtrate was evaporated under reduced 30. pressure to leave 37.4 g of 2,4-dichloro-5-methoxy- acetanilide as a solid. Step D: 2,4-Dichloro-5-methoxyaniline In the manner of Example 2, Step C, the reaction of 37.4 g (0.16 mole) of 2,4-dichloro-5-methoxyacetanilide 35 with 12.8 g (0.32 mole) of sodium hydroxide in 30 mL of water and 30 mL of ethanol produced 16.7 g of 2,4-di- chloro-5-methoxyaniline. 1 -(2,4-Dichloro-5-methoxyphenyl)-1 ,4-dihydro-4- methyl-5H-tetrazol-5-one (compound 6) and compounds 7, 9 and 14-20 of Table 1 were prepared from 2,4-dichloro-5- methoxyaniline using the method described in .Steps D, E and F of Example 2. Compounds 21-27, 30, 37, 73, 77, 100 and 101 were also prepared by the method of Example 2, Steps D, E, and F from the corresponding 2,4-di- chloro-5-alkoxyaniline compounds which were prepared in the manner of Example 3. Example 4 1-(2,4-DIFLUORO-5-METHOXYPHENYL)-1 ,4-DIHYDRO-4- ETHYL-5H-TETRAZOL-5-ONE Step A: 2,4-Difluoro-5-methoxyaniline Hydrogenation of 3.0 g (0.017 mole) of 2,4-di- -fluoro-5-methoxy-1-nitrobenzene in the presence of 0.1 g of platinum oxide and 0.3 mL of orpholine in 110 mL of absolute ethanol produced 1.5 g of 2,4-difluoro-5-meth- oxyaniline as a solid, mp 43-45 β C. The nmr and ir spectra were consistent with the proposed structure. 1-(2,4-Difluoro-5-methoxyphenyl)-1 ,4-dihydro-4- ethyl-5H-tetrazol-5-one (compound 8) and compound 10 of Table 1 were prepared from 2,4-difluoro-5-methoxyaniline by the method of Example 2, Steps D, E, and F. Example 5 1-(4-CHLORO-2-FLUORO-5-METHOXYPHENYL)-1 ,4- DIHYDRO-4-PROPYL-5H-TETRAZOL-5-ONE Step A: 2-Chloro-4-fluorophenyl 4-methylphenyl- sulfonate stirred solution of 20.0 g (0.137 mole) of 2-chloro-4-fluorophenol in 150 mL of pyridine was cooled in an ice bath. To this solution was added portionwise 31.2 g (0.164 mole) of 4-methylphenylsulfonyl chloride. After complete addition, the mixture was stirred for 2 hours, then allowed to stand in a freezer for approxi¬ mately 16 hours. The mixture was poured into ice water. filtered, and the filter cake washed with water. The solid was dried in a dessicator to yield 41.0 g of 2-chloro-4-fluorophenyl 4-methylphenylsulfonate, mp 92-94 β C. 5 J Step B: 2-Chloro-4-fluoro-5-nitrophenyl 4-methyl- 3-nitrophenylsulfonate Nitration of 41.0 g (0.16 mole) of 2-chloro-4- fluorophenyl 4-methylphenylsulfonate in 340 mL of fuming nitric acid produced a solid which was recrystallized 10 from ethanol to yield 40.0 g of 2-chloro-4-fluoro-5- nitrophenyl 4-methyl-3-nitrophenylsulfonate. Step C: 2-Chloro-4-fluoro-5-nitrophenol A solution of 12.84 g (0.195 mole) of potassium hydroxide in 200 mL of water was added to a vigorously 15 stirred solution of 34.0 g (0.097 mole) of 2-chloro-4- fluoro-5-nitrophenyl 4-methyl-3-nitrophenylsulfonate in 190 mL of p-dioxane. The resultant mixture was stirred at room temperature for approximately 18 hours. The reaction mixture was filtered and the filtrate acidified 20 with concentrated hydrochloric acid. The acidic solution was extracted with diethyl ether. The ether extract was dried over anhydrous sodium sulfate, fil¬ tered, and the solvent evaporated under reduced pressure to leave a solid. The solid was washed with petroleum 25 ether to yield 15.07 g of 2-chloro-4-fluoro-5-nitro- phenol. Step D: 1-Chloro-5-fluoro-2-methoxy-4-nitro- benzene To a stirred solution of 8.0 g (0.042 mole) of 30. 2-chloro-4-fluoro-5-nitrophenol in 200 mL of acetone was added 6.09 g (0.0435 mole) of potassium carbonate. The mixture was heated at reflux temperature for 15 minutes, and 8.9 g (0.063 mole) of iodomethane was added. The resultant mixture was heated at reflux temperature for 5 5 hours, then stirred at room temperature for approxi¬ mately 18 hours. The mixture was filtered and the v •■ ■ - - ---. C. * O FI Yλ ^ WIPO ^N TlO filtrate evaporated under reduced pressure to leave a residue. The residue was dissolved in diethyl ether, filtered, and the filtrate washed with a saturated sodium chloride solution. The ether solution was dried over anhydrous sodium sulfate, filtered, and the fil¬ trate evaporated to yield 6.6 g of 1-chloro-5-fluoro- 2-methoxy-4-nitrobenzene as a solid, 63-65 * C. The nmr spectrum was consistent with the proposed structure. Step E: 4-Chloro-2-fluoro-5-methoxyaniline Hydrogenation of 6.6 g (0.032 mole) of 1-chloro-5- fluoro-2-methoxy-4-nitrobenzene in the presence of 0.2 g of platinum oxide and 0.7 g (0.008 mole) of pyridine in 200 mL of absolute ethanol produced 6.5 g of 4-chloro-2- fluoro-5-methoxyaniline. 1-(4-Chloro-2-fluoro-5-methoxyphenyl)-1 ,4-dihydro- 4-propyl-5H-tetrazol-5-one (compound 11) was prepared by the method described in Example 2, Steps D, E, and F from 4-chloro-2-fluoro-5-methoxyaniline. Example 6 1-( 4-BROMO-2-CHLORO-5-METHOXYPHENYD-1 ,4- DIHYDRO-4-PROPYL-5H-TETRAZOL-5-ONE Step A: 4-Bromo-2-chloro-5-methoxyaniline A stirred solution of 9.7 g (0.050 mole) of 2- chloro-5-methoxyaniline hydrochloride in 120 mL of acetic acid was cooled to 15 β C. To this cold mixture was added 4.0 g (0.025 mole) of bromine. After complete addition, the mixture was allowed to warm to room temperature and was stirred for approximately 18 hours. The mixture was poured into ice water. To the resultant mixture was added a solution of 2.0 g (0.05 mole) of sodium hydroxide in 10 mL of water. This mixture was extracted with 200 mL of diethyl ether. The ether extract was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to leave an oil. The oil was purified by column chromatography on silica gel, eluting with methylene chloride, to yield 7.3 g of 4-bromo-2-chloro- 5-methoxyaniline as a solid, mp 40-41 β C. 1-(4-Bromo-2-chloro-5-methoxyphenyl)-1 ,4-dihydro- 4-propyl-5H-tetrazol-5-one (compound 12) was prepared from 4-bromo-2-chloro-5-methoxyaniline by the method of Example 2, Steps D, E, and F. Example 7 1-(2-BROMO-4-CHLORO-5-METHOXYPHENYL)- 1 ,4-DIHYDRO-4-PROPYL-5H-TETRAZOL-5-ONE Step A: 5-Methoxyacetanilide In the manner of Example 2, Step A, the reaction of 103.1 g (0.837 mole) of 3-methoxyaniline and 170.5 g (1.67 moles) of acetic anhydride in 300 mL of water produced 138.0 g of 5-methoxyacetanilide as a solid, mp 60-62 β C. Step B: 4-Chloro-5-methoxyacetanilide In the manner of Example 2, Step B, the reaction of 50.0 g (0.303 mole) of 5-methoxyacetanilide with 40.9 g (0.303 mole) of sulfuryl chloride in 300 L of chloro¬ form produced a solid. The solid was triturated in ethyl acetate:n-hexane and collected on a filter paper to give 17.0 g of a solid. Recrystallization from ethyl acetate:n-hexane provided 4.3 g of 4-chloro-5-methoxy- acetanilide, mp 83-85 # C. The nmr spectrum was consistent with the proposed structure. Step C: 2-Bromo- -chloro-5-methoxyacetanilide Bromination of 4.0 g (0.03 mole) of 4-chloro-5- methoxyacetanilide with 3.2 g (0.02 mole) of bromine in 50 mL of glacial acetic acid produced 3.9 g of 2-bromo- 4-chloro-5-methoxyacetanilide as a solid, mp 143-145 β C. The nmr spectrum was consistent with the proposed structure. Step D: 2-Bromo-4-chloro-5-methoxyaniline In the manner of Example 2, Step C, the reaction of 3.9 g (0.013 mole) of 2-bromo-4-chloro-5-methoxy- acetanilide with 1.13 g (0.028 mole) of sodium hydroxide in 30 mL of water and 25 mL of ethanol produced 2.9 g of 2-bromo-4-chloro-5-methoxyaniline. The nmr and ir spectra were consistent with the proposed structure. 1-(2-Bromo-4-chloro-5-methoxyphenyl)-1 ,4-dihydro- 4-propyl-5H-tetrazol-5-one (compound 13) was prepared from 2-bromo-4-chloro-5-methoxyaniline using the method of Example 2, Steps D, E, and F. Example 8 1-[2,4-DIBROMO-5-(1-METHYLETHOXY)PHENYL]-1,4- DIHYDRO-4-(2-PROPENYL)-5H-TETRAZOL-5-ONE Step A: 2,4-Dibromo-5-hydroxyacetanilide Using the method of Example 6, the bromination of 30.2 g (0.20 mole) of 3-hydroxyacetanilide (Example 3, Step A) with 32 g (0.20 mole) of bromine in 100 mL of glacial acetic acid produced a solid. The solid was treated with an additional 32.0 g (0.20 mole) of bromine in 400 mL of glacial acetic acid to yield 12.5 g of 2,4-dibromo-5-hydroxyacetanilide as a solid, mp 233-240 β C. Step B: 2,4-Dibromo-5-(1-methylethoxy)acetanilide To a stirred mixture of 12.0 g (0.038 mole) of 2,4-dibromo-5-hydroxyacetanilide in 80 mL of acetone was added 7.0 g (0.050 mole) of potassium carbonate followed by 8.0 g (0.050 mole) of 2-iodopropane. The mixture was heated at reflux temperature for approximately 18 hours, cooled, then filtered. The filtrate was evaporated to leave a solid which was recrystallized from ethanol to produce 11.7 g of 2,4-dibromo-5-(1-methylethoxy)- acetanilide, mp 129-130 *' C. Step C: 2,4-Dibromo-5-( 1-methylethoxy)aniline A stirred mixture of 11.7 g (0.038 mole) of 2,4- dibromo-5-(1-methylethoxy)acetanilide in 100 mL of dilute hydrochloric acid was heated at reflux tempera- ture for 30 minutes. The reaction mixture was cooled, filtered, and the filter cake suspended in 100 mL of water. To the aqueous suspension was added 4.0 g (0.038 mole) of sodium carbonate, and the resulting mixture was stirred for approximately 1 hour. The mixture was filtered and the filter cake dried under reduced pres¬ sure to yield 6.2 g of 2,4-dibromo-5-(1-methylethoxy)- aniline. 1-[2,4-Dibromo-5-( 1-methylethoxy)phenyl]-1 ,4-di- hydro-4-(2-propenyl)-5H-tetrazol-5-one (compound 28) and compound 29 of Table 1 were prepared from 2,4-dibromo-5- ( 1-methylethoxy)aniline by the method of Example 2, Steps D, E, and F. Example 9 ' 1-(4-CHLORO-5-METHOXY-2-METHYLPHENYL-1 ,4- DIHYDRO-4-PROPYL-5H-TETRA20L-5-ONE Step A: 1-Methoxy-4-methyl-3-nitrobenzene In the manner of Example 8, Step C, the reaction of 25.0 g (0.162 mole) of 4-methyl-3-nitrophenol, 23.3 g (0.168 mole) of potassium carbonate, and 34.1 g (0.24 mole) of methyl iodide produced 26.4 g of 1-methoxy-4- methyl-3-nitrobenzene as an oil. The nmr spectrum was consistent with the proposed structure. Step B: 5-Methoxy-2-methylaniline Hydrogenation of 26.4 g (0.157 mole) of 1-methoxy- 4-methyl-3-nitrobenzene in the presence of 0.5 g of platinum oxide in 200 mL of absolute ethanol produced 20.2 g of 5-n.ethoxy-2-methylaniline as a solid, mp 36-38 β C. The nmr spectrum was consistent with the proposed structure. Step C: 5-Methoxy-2-methylacetanilide In the manner of Example 2, Step A, the reaction of 19.4 g (0.14 mole) of 5-methoxy-2-methylaniline with 28.2 g (0.28 mole) of acetic anhydride in 100 mL of O .PI water produced 17.1 g of 5-methoxy-2-methylacetanilide as a solid, 68-70 β C. The nmr spectrum was consistent with the proposed structure. Step D: 4-Chloro-5-methoxy-2-methylacetanilide In the manner of Example 2, Step B, the chlorina- tion of 16.0 g (0.089 mole) of 5-methoxy-2-methylaceta- nilide with 12.0 g (0.089 mole) of sulfuryl chloride in 150 mL of chloroform produced 13.3 g of 4-chloro-5- methoxyacetanilide as a solid, mp 170-171 β C. The nmr spectrum was consistent with the proposed structure. Step E: 2-Chloro-5-methoxy-2-methylaniline In the manner of Example 2, Step C, the reaction of 13.3 g (0.062 mole) of 4-chloro-5-methoxyacetanilide with 5.0 g (0.125 mole) of sodium hydroxide in 125 mL of water and 125 mL of ethanol produced 4.5 g of 2-chloro- 5-methoxy-2-methylaniline as a solid, mp 83-85 β C. 1-(4-Chloro-5-methoxy-2-methylphenyl)-1 ,4-dihydro- 4-propyl-5H-tetrazol-5-one (compound 95) and compound 96 of Table 1 were produced front 2-chloro-5-methoxy-2- methylaniline by the method of Example 2, Steps D, E, and F. Example 10 1-[2,4-DICHLORO-5-(3-IODO-2-PROPYNYLOXY)PHENYL]- 1 ,4-DIHYDRO-4-PROPYL-5H-TETRAZOL-5-ONE Step A: 1-(2,4-Dichloro-5-hydroxyphenyl)-1 ,4-di- hydro-4-propyl-5H-tetrazol-5-one A stirred mixture of 2.0 g (0.0066 mole) of 1-(2,4- dichloro-5-methoxyphenyl)-1 ,4-dihydro-4-propyl-5H-tetra- zol-5-one (compound 9) and 30 mL of concentrated hydro¬ bromic acid was heated at reflux temperature for approx¬ imately 18 hours. The reaction mixture was cooled, filtered, and the filter cake dissolved in methylene chloride. The methylene chloride solution was eva¬ porated under reduced pressure to leave 1.35 g of 1-(2,4-dichloro-5-hydroxyphenyl)-1 ,4-dihydro-4-propyl- 5H-tetrazol-5-one as a solid, mp 125-128'C. The nmr spectrum was consistent with the proposed structure. Step B: 1-[2,4-Dichloro-5-(2-propynyloxy)phenyl]- 1 ,4-dihydro-4-propyl-5H-tetrazol-5-one To a stirred solution of 0.5 g (0.0017 mole) of 1-(2,4-dichloro-5-hydroxyphenyl)-1 ,4-dihydro-4-propyl- 5H-tetrazol-5-one in 15 mL of anhydrous N,N-dimethyl- formamide was added 0.11 g (0.0019 mole) of potassium fluoride, several drops of 18-crown-6, and 0.14 g (0.0019 mole) of propargyl chloride. The mixture was stirred at 80 β C for approximately 20 hours, then cooled to room temperature. A portion of the solvent was removed by distillation under reduced pressure, and the remainder of the mixture was poured into water. The aqueous mixture was extracted with ethyl acetate, and the organic layer washed with a saturated aqueous solution of sodium chloride. The organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated under reduced pressure to leave a residue. The residue was purified by column chroma- tography on silica gel, eluting with ethyl acetate: n-hexane (15:85), to yield 0.27 g of 1-[2,4-di.chloro- 5-(2-propynyloxy)phenyl]-1 ,4-dihydro-4-propyl-5H-tetra- zol-5-one as a solid, mp 70-72 β C. The nmr spectrum was consistent with the proposed structure. This experiment was repeated on a larger scale to obtain additional quantities of 1-[2,4-dichloro-5-(2- propynyloxy)phenyl]-1 ,4-dihydro-4-propyl-5H-tetrazol- 5-one. The tetrazolinone prepared in Example 10, Steps A and B is listed in Table 1 as compound 45. Other tetrazolinones prepared in a similar manner are com¬ pounds 31, 32, 34, 38-42, 45, 46, 49, 50, 57, 58, 63-65, 80 and 91-93. In some instances 18-crown-6 was not used. Also, in some instances, acetone was used as the solvent in place of N,N-dimethylformamide. Step Ct 1-[2,4-Dichloro-5-(3-iodo-2-proρynyloxy)- phenyl]-1 ,4-dihydro-4-propyl-5H-tetrazol-5-one To a cold solution of 0.5 g (0.00153 mole) of 1-r2,4-dichloro-5-(2-propynyloxy)phenyl]-1 ,4-dihydro-4- proρyl-5H-tetrazol-5-one in 20 mL of methanol was added 2 mL of a saturated aqueous solution of sodium hydroxide and an additional 10 mL of methanol.. To this mixture was added a solution of 0.39 g (0.00153 mole) of iodine in 5 mL of methanol. After complete addition, the reaction mixture was allowed to warm to room tem¬ perature and was stirred for approximately 18 hours. The reaction mixture was filtered and a solid collected. The solid was purified by column chromatography to yield 0.14 g of 1-[2,4-dichloro-5-(3-iodo-2-propynyloxy)- phenyl]-1 ,4-dihydro-4-propyl-5H-tetrazol-5-one as a solid, mp 134-138 β C. The nmr spectrum was consistent with the proposed structure. The tetrazolinone prepared in Step C is listed in Table 1 as compound 61. Example 11 1- [2 ,4-DIFLUORO-5-( 1-METHYLETHOXY)PHENYL] - 1 ,4-DIHYDRO-4-PROPYL-5H-TETRAZOL-5-ONE Step A: 1-(2,4-Difluoro-5-hydroxyphenyl)-1 ,4- dihydro-4-propyl-5H-tetrazol-5-one Under a dry nitrogen atmosphere a stirred solution of 0.18 g (0.00067 mole) of 1-(2,4-difluoro-5-methoxy- phenyl)-1 ,4-dihydro-4-propyl-5H-tetrazol-5-one (compound 10) in 5 mL of methylene chloride was cooled to -40 β C. To this cold solution was added dropwise a solution of 0.5 g (0.002 mole) of boron tribromide in 5 mL of methylene chloride. After complete addition, the mixture was allowed to warm to room temperature and was OMPI stirred for approximately 70 hours. The mixture was poured into ice water and the two phases separated. The aqueous phase was extracted with methylene chloride. The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was evapo¬ rated to leave 0.14 g of 1-(2,4-difluoro-5-hydroxy- phenyl)-1 ,4-dihydro-4-propyl-5H-tetrazol-5-one as a solid, mp 65-67 β C. The nmr spectrum was consistent with the proposed structure. This reaction was repeated to obtain additional quantities of product. Step B: 1-(2,4-Difluoro-5-(1-methylethoxy)phenyl]- 1 ,4-dihydro-4-propyl-5H-tetrazol-5-one A stirred mixture of 0.87 g (0.0034 mole) of 1-(2,4-difluoro-5-hydroxyphenyl)-1 ,4-dihydro-4-propyl- 5H-tetrazol-5-one, 0.7 g (0.0051 mole) of potassium carbonate, and 1.2 g (0.007 mole) of 2-iodopropane in 40 mL of acetone was heated at reflux for approximately 18 hours. The mixture was cooled, filtered, and the solvent evaporated under reduced pressure to leave an oil. The oil was purified by filtration through a small amount of silica gel followed by crystallization from heptane to yield 0.38 g of 1-[2,4-difluoro-5-(1-methyl- ethoxy)phenyl]-1 ,4-dihydro-4-propyl-5H-tetrazol-5-one, mp 76.5-77 β C. The tetrazolinone prepared in Example 11 is listed in Table 1 as compound 35. Other tetrazolinones pre¬ pared by this method were compounds 36, 43, 48, 51-53, 55, 56, 59, 60, 67, 74, 75, 78, 83-85 and 97-99. In some cases the intermediate 5-hydroxyphenyl compound was prepared by the method of Example 10, Step A. Example 12 1-t2,4-DICHLORO-5-(2-BUTYNYLOXY) HENYL]-1,4- DIHYDRO-4-PROPYL-5H-TETRAZOL-5-ONE To a stirred solution of 0.5 g (0.0017 mole) of OMPI ° 1-(2,4-dichloro-5-hydroxyphenyl)-1 ,4-dihydro-4-propyl- 5H-tetrazol-5-one (Example 10, Step A) and 0.15 g (0.0021 mole) of 2-butyn-1-ol in 5 mL of acetonitrile was added 0.33 g (0.0016 mole) of dicyclohexylcar- bodiimide. The reaction mixture was heated at reflux temperature for 4 days, cooled to room temperature, and filtered. The filtrate was washed with 10 mL of a 10% aqueous sodium hydroxide solution, diluted with methyl¬ ene chloride, and washed with 10 L of 6 N hydrochloric acid. The washed organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated to leave an oil. The oil was purified by column chroma¬ tography on silica gel, eluting with ethyl acetate: heptane (20:80), to yield 0.12 g of 1-[2,4-dichloro-5- (2-butynyloxy)phenyl]-1 ,4-dihydro-4-propyl-5H-tetrazol- 5-one as a solid, mp 58-60 * C. The nmr and ir spectra were consistent with the proposed structure. The tetrazolinone prepared in Example 12 is listed as compound 62 in Table 1. Example 13 1-(2,4-DICHLORO-5-METHOXYMETHOXYPHENYD-1 ,4- DIHYDRO-4-ETHYL-5H-TETRAZOL-5-ONE Step A: 1-(2,4-Dichloro-5-hydroxyphenyl)-1 ,4- dihydro-4-ethyi-5H-tetrazol-5-one In the manner of Example 11, Step A, the reaction of 1.56 g (0.0054 mole) of 1-(2,4-dichloro-5-methoxy- phenyl)-1 ,4-dihydro-4-ethyl-5H-tetrazol-5-one (compound 7) and 4.06 g (0.016 mole) of boron tribromide in 20 mL of methylene chloride produced 1.25 g of 1-(2,4-di- chloro-5-hydroxyphenyl)-1 ,4-dihydro-4-ethyl-5H-tetrazol- 5-one, mp 149-150'C. Step B: 1-(2,4-Dichloro-5-methoxymethoxyphenyl)- 1 ,4-dihydro-4-ethyl-5H-tetrazol-5-one To a stirred mixture of 0.8 g (0.0029 mole) of 1-(2,4-dichloro-5-hydroxyphenyl)-1 ,4-dihydro-4-ethyl- OMPI YA/ , WIPO ■ 5H-tetrazol-5-one, 2.8 g (0.032 mole) of N,N-dimethyl- acetamide, and 0.14 g (0.0029 mole) of sodium hydride (50% in oil) in 25 L of toluene was added 0.47 g (0.0058 mole) of chloromethyl methyl ether. The reaction mixture was stirred at room temperature for approximately 18 hours then poured into ice water and extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated to leave a solid. The solid was purified by recrystallization from heptane to yield 0.19 g of 1-(2,4-dichloro-5-methoxymethoxyphenyl)-1 ,4- dihydro-4-ethyl-5H-tetrazol-5-one, mp 112-113"C. The nmr spectrum was consistent with the proposed structure. " The tetrazolinone prepared in Example 13 is listed as compound 66 in Table 1. Other tetrazolinones pre¬ pared by this method were compounds 68-72. Example 14 1-[2 ,4-DICHLORO-5-(2-TETRAHYDROFURANYLOXY)PHENYL]- 1 ,4-DIHYDRO-4-PROPYL-5H-TETRAZOL-5-ONE To a stirred solution of 1.0 g (0.0035 mole) of 1-(2,4-dichlo o-5-hydroxyphenyl)-1 ,4-dihydro-4-propyl- 5H-tetrazol-5-one (Example 10, Step A.) and 0.05 g (0.00026 mole) of 4-methylphenylsulfonic acid in 40 mL of p-dioxane was added slowly 0.88 g (0.0126 mole) of dihydrofuran in 20 mL of p-dioxane. The mixture was stirred at room temperature for approximately 18 hours, and an additional 0.88 g of dihydrofuran was added. The mixture was stirred at room temperature for an additional 48 hours. One mL of methanol saturated with ammonia was added to the mixture and stirring was continued for a short period of time. The reaction mixture was evaporated under reduced pressure to leave a residue. The residue was purified by column chromato- graphy on silica gel, eluting with methylene chloride, to yield 0.58 g of 1-[2,4-dichloro-5-(2-tetrahydro- f ur anyloxy ) phe nyl ] - 1 , 4-d ihydro-4-propyl-5H-tet razol-5- one as a solid, mp 89-90 β C. The nmr spectrum was consistent with the proposed structure. The tetrazolinone of Example 14 is listed as compound 76 in Table 1. Compounds 79, 102, and 103 were also prepared by this process. Example 15 1-( 5-ACE YLOXY-2,4-DICHLOROPHENYL)-1 ,4- DIHYDRO-4-PROPYL-5H-TETRAZOL-5-ONE To a stirred mixture of 0.1 g (0.0021 mole) of sodium hydride (50% in oil) in 30 mL of tetrahydrofuran was added slowly 0.5 g (0.0017 mole) of 1-(2,4-dichloro- 5-hydroxyphenyl)-1 ,4-dihydro-5H-tetrazol-5-one (Example 10, Step A). The mixture was stirred for 15 minutes and 0.16 g (0.0021 mole) of acetyl chloride was slowly added. The reaction mixture was stirred at room temper¬ ature for approximately 18 hours. The mixture was poured into ice water, and the resulting precipitate was collected on a filter paper. Recrystallization from ethyl acetate: heptane gave 0.15 g of 1-(5-acetoxy-2,4- dichlorophenyl)-1 ,4-dihydro-4-propyl-5H-tetrazol-5-one, mp 91-92 β C. The nmr spectrum was consistent with the proposed structure. The tetrazolinone prepared in Example 15 is listed in Table 1 as compound 81. Example 16 2,4-DICHLORO-5-( 1 ,4-DIHYDRO-5-OXO-4-PROPYL- TETRAZOL-1-YDPHENOXYACETIC ACID A stirred solution of 0.5 g (0.0014 mole) of methyl 2,4-dichloro-5-( 1 ,4-dihydro-5-oxo-4-propyltetrazol-l- yUphenoxyacetate (compound 83) and 0.08 g (0.0021 mole) of sodium hydroxide in 10 mL of methanol was heated at reflux temperature for 1.5 hours. The reaction mixture was cooled, then evaporated under reduced pressure to leave a solid residue. The residue was dissolved in 20 mL of water, and the solution acidified with con¬ centrated hydrochloric acid. A solid precipitate formed and was collected by filtration and washed with cold water. Recrystallization from diethyl ether:pentane provided 0.2 g of 2,4-dichloro-5-(1,4-dihydro-5-oxo-4- propyltetrazol-l-yl)phenoxyacetic acid, mp 134-136 * C. The nmr spectrum was consistent with the proposed structure. The tetrazolinone prepared in Example 16 is listed in Table 1 as compound 82. Example 17 1-(2,4-DICHLORO-5-METHYLSULFONYLOXYPHENYL)- 1 ,4-DIHYDRO-4-PROPYL-5H-TETRAZOL-5-ONE A stirred solution of 0.5 g (0.0017 mole) of 1-(2,4-dichloro-5-hydroxyphenyl)-1 ,4-dihydro-4-propyl- 5H-tetrazol-5-one (Example 10, Step A) and 0.26 g (0.0026 mole) of triethylamine in 30 mL of methylene chloride was cooled to 0 β C. Methanesulfonyl chloride (0.22 g, 0.0019 mole) was added slowly to the reaction mixture. After complete addition, the mixture was allowed to warm to room temperature and was stirred for several days. The mixture was poured into ice water and extracted with diethyl ether. The ether extract was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to leave a residue. The residue was purified by column chromato¬ graphy on silica gel to yield 0.33 g of 1-(2,4-dichloro- 5-methylsulfonyloxyphenyl)-l ,4-dihydro-4-propyl-5H- tetrazol-5-one was a solid, mp 64-65 β C. The nmr spectrum was consistent with the proposed structure. The tetrazolinone prepared in Example 17 is listed in Table 1 as compound 86. Compounds 87-89 were also prepared by this method. Example 18 1-(2-CHLORO-5-METHOXY-4-TRIFLUOROMETHYLPHENYL)- 1 ,4-DIHYDRO-4-PROPYL-5H-TETRAZOL-5-ONE Under a dry nitrogen atmosphere a stirred mixture of 6.0 g (0.044 mole) of sodium trifluoroacetate and 4.18 g (0.022 mole) of copper(I) iodide in 40 L of N,N-dimethylacetamide was heated at 150 * C. To the hot mixture was added 3.3 g (0.011 mole) of 1-(4-bro_no-2- chloro-5-methoxyphenyl)-1 ,4-dihydro-4-propyl-5H-tetra- zol-5-one (compound 12). After complete addition, the hot mixture was stirred for 3 hours then allowed to cool to room temperature. The mixture was filtered and the filtrate diluted with ice water to form a preci¬ pitate. The solid was collected by filtration and purified, first by column chromatography on silica gel eluting with methylene chloride:heptane (80:20), then by recrystallization from heptane to yield 0.7 g of 1-(2-chloro-5-methoxy-4-trifluoromethylphenyl)-l ,4-di- hydro-4-propyl-5H-tetrazol-5-one, mp 82-83 β C. The nmr spectrum was consistent with the proposed structure. The tetrazolinone prepared in Example 18 is listed in Table 1 as compound 94. Compound 108 was also prepared by this method. Example 19 1- t2-CHLORO-4-FLUORO-5-(2-PROPYNYLOXY)PHENYL]- 1 ,4-DIHYDRO-4-ETHYL-5H-TETRAZOL-5-ONE Step A: Di-4-chloro-2-fluorophenyl carbonate A stirred solution of 11.5 g (0.078 mole) of 2-fluoro-4-chlorophenol sodium salt in 80 mL of .p- dioxane and 30 L of water was cooled to 5-10 β C. A solution of phosgene in toluene (35 mL of a 12.5% solution, 0.039 mole phosgene) was added slowly to the cold reaction mixture. After complete addition, the mixture was stirred at room temperature for approxi¬ mately 18 hours. The mixture was poured into ice water WXEA XT O PI and the organic phase separated. The organic phase was dried over anhydrous magnesium sullfate, filtered, and the filtrate evaporated to leave an oil. The oil was purified by crystallization from petroleum ether to yield 6.0 g of di-4-chloro-2-fluorophenyl carbonate, mp 89-90 β C. Step B: Di-4-chloro-2-fluoro-5-nitrophenyl car¬ bonate To 50 mL- of fuming nitric acid, cooled to 10 β C, was added 6.0 g (0.02 mole) of di-4-chloro-2-fluorophenyl carbonate. After complete addition, the mixture was stirred for 30 minutes at 10'C then poured into ice water. A solid formed and was collected by filtration and rinsed with water to yield 7.5 g of di-4-chloro-2- fluoro-5-nitrophenyl carbonate. Step C: 4-Chloro-2-fluoro-5-nitrophenol A solution of 1.2 g (0.03 mole) of sodium hydroxide in 30 mL of water was added to a stirred solution of 7.5 g (0.019 mole) of di-4-chloro-2-fluoro-5-nitrophenyl carbonate in 60 mL of p-dioxane. After complete addi¬ tion, the mixture was stirred for 1 hour. The mixture was diluted with 100 mL of water and the resulting solution neutralized with concentrated hydrochloric acid. A solid formed and was collected by filtration and washed with petroleum ether to yield 6.0 g of 4-chloro-2-fluoro-5-nitrophenol, mp 85-86 β C. The nmr spectrum was consistent with the proposed structure. Step D: 1-Chloro-3-fluoro-4-methoxy-6-nitrobenzene in the manner of Example 3, Step C, the reaction of 6.0 g (0.031 mole) of 4-chloro-2-fluoro-5-nitrophenol, 6.35 g (0.046 mole) of potassium carbonate, and 8.8 g (0.062 mole) of methyl iodide in 80 mL of acetone produced 6.1 g of 1-chloro-3-fluoro-4-methoxy-6-nitro- benzene as a solid, mp 80-81 β C. Step E: 2-Chloro-4-fluoro-5-methoxyaniline OMPI The hydrogenation of 4.5 g (0.022 mole) of 1- chloro-3-fluoro-4-methoxy-6-nitrobenzene in the presence of 0.15 g of platinum oxide in 200 mL of absolute ethanol produced 3.2 g of 2-chloro-4-fluoro-5-meth- oxyaniline. Step F: 2-Chloro-4-fluoro-5-methoxyphenyl iso¬ cyanate In the manner of Example 2, Step D, the reaction of 3.0 g (0.017 mole) of 2-chloro-4-fluoro-5-methoxyaniline with 1.68 g (0.0085 mole) of trichloromethyl chlorofor- mate in 20 mL of toluene produced 3.0 g of 2-chloro-4- fluoro-5-methoxyphenyl isocyanate. Step G: 1-(2-Chloro-4-fluoro-5-methoxyphenyl)- 1 ,4-dihydro-5H-tetrazol-5-one In the manner of Example 2, Step E, the reaction of 3.2 g (0.016 mole) of 2-chloro-4-fluoro-5-methoxyphenyl isocyanate with 3.2 g (0.028 mole) of trimethylsilyl azide produced 3.0 g of 1-(2-chloro-4-fluoro-5-meth- oxyphenyl)-1 ,4-dihydro-5H-tetrazol-5-one. Step H: 1-(2-Chloro-4-fluoro-5-methoxyphenyl)- 1 ,4-dihydro-4-ethyl-1 ,4-dihydro-5H-tetrazol-5-one In the manner of Example 2, Step F, the reaction of 1.33 g (0.0054 mole) of 1-(2-chloro-4-fluoro-5-meth- oxyphenyl)-1 ,4-dihydro-5H-tetrazol-5-one with 0.26 g (0.0054 mole) of sodium hydride and 1.6 g (0.01 mole) of iodoethane in 60 mL of dimethylsulfoxide produced 1.26 g of 1-(2-chloro-4-fluoro-5-methoxyphenyl)-l ,4-dihydro-4- ethyl-5H-tetrazol-5-one, compound 105, 79-80 β C. Com¬ pound 106 was prepared in a similar manner. Step I: 1-(2-Chloro-4-fluoro-5-hydroxyphenyl)-1 ,4- dihydro-4-ethyl-5H-tetrazol-5-one In the manner of Example 11 , Step A, the reaction of 0.9 g (0.0033 mole) of l-(2-chloro-4-fluoro-5-meth- oxyphenyl)-1 ,4-dihydro-4-ethyl-5H-tetrazol-5-one with 2.5 g (0.01 mole) of boron tribromide in 15 mL of methylene chloride produced 0.8 g of 1-(2-chloro-4- fluoro-5-hydroxyphenyl)-1 ,4-dihydro-4-ethyl-5H-tetrazol- 5-one. Sept J: 1-[2-Chloro-4-fluoro-5-(2-propynyloxy)- phenyl]-1 ,4-dihydro-4-ethyl-5H-tetrazol-5-one In the manner of Example 8, Step B, the reaction of 0.8 g (0.0031 mole) of l-(2-chloro-4-fluoro-5-hydroxy- phenyl)-1 ,4-dihydro-4-ethyl-5H-tetrazol-5-one with 0.9 g (0.0062 mole) of 1-bromo-2-propyne and 0.63 g (0.0046 mole) of potassium carbonate in 25 L of acetone pro- duced 0.6 g of 1-[2-chloro-4-fluoro-5-(2-propynyloxy)- phenyl] -1 ,4-dihydro-4-ethyl-5H-tetrazol-5-one, mp 88-89 β C, The nmr spectrum was consistent with the proposed structure. The tetrazolinone prepared in Example 19 is listed in Table 1 as compound 44. Compound 47 was also pre¬ pared by the process described in this Example. Example 20 1-(2,4-DICHLORO-5-METHOXYPHENYL)-4-ETHENYL- 1 ,4-DIHYDRO-5H-TETRAZOL-5-ONE Step A: 1-(2 ,4-Dichloro-5-methoxyphenyl )-1 ,4- dihydro-4-(2-hydroxyethyl)-5H-tetrazol-5-one In the manner of Example 10, Step B, 3.3 g (0.058 mole) of potassium fluoride was reacted with 3.0 g (0.0115 mole) of 1-(2,4-dichloro-5-methoxyphenyl)-1 ,4- dihydro-5H-tetrazol-5-one (prepared from 2,4-dichloro- 5-methoxyaniline , Example 3, using the process of Example 2, Steps D and E) in 45 mL of N,N-dimethyl- formamide. Subsequent treatment with 5.9 g (0.035 mole) of 2-iodoethanol produced 1.1 g of 1-(2,4-dichloro-5- methoxyphenyl)-2,5-dihydro-4-(2-hydroxyethyl)-5H-tetra- zol-5-one as a solid, mp 109-110 β C. Step B: 1-(2,4-Dichloro-5-methoxyphenyl)-1 ,4-di- hydro-4- [2-(methylsulf onyloxy) ethyl] -5H-tetrazol-5-one A stirred solution of 0.9 g (0.003 mole) of 1-(2,4- dichloro-5-methoxyphenyl)-1 ,4-dihydro-4-( 2-hydroxy- ethyl)-5H-tetrazol-5-one and 0.45 g (0.0044 mole) of triethylamine in 35 mL of methylene chloride was cooled to 0*C. To the cool solution was added 0.37 g (0.0033 mole) of methanesulfonyl chloride. After complete addition, the mixture was allowed to warm to room temperature and was stirred for approximately 18 hours. The mixture was poured into ice water. Sodium chloride was added and the mixture was extracted with diethyl ether. The ether extract was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to yield 1.0 g of 1-(2,4-di- chloro-5-methoxyphenyl)-1 ,4-dihydro-4-[2-(methylsul- fonyloxy)ethyl]-5H-tetrazol-5-one as an oil. Step C: 1-(2,4-Dichloro-5-methoxyphenyl)-4- ethenyl-1 ,4-dihydro-5H-tetrazol-5-one A stirred mixture of 0.38 g (0.0066 mole) of potassium fluoride and 0.85 g (0.0022 mole) of 1-(2,4- dichloro-5-methoxyphenyl)-1 ,4-dihydro-4-[2(methylsul- fonyloxy)ethyl]-5H-tetrazol-5-one in 35 mL of N,N-di- methylformamide was heated at 120-130 β C for 2 hours, then stirred at room temperature for 3 days. The reaction mixture was poured into ice water then ex¬ tracted with diethyl ether. The ether extract was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to leave a residue. The residue was purified by column chromato- graphy on silica gel, eluting with methylene chloride, then recrystallized from ethyl acetate:heptane to yield 0.25 g of 1-(2,4-dichloro-5-methoxyphenyl)-4-ethenyl- 1 ,4-dihydro-5H-tetrazol-5-one, mp 142-143 β C. The nmr and ir spectra were consistent with the proposed structure. The tetrazolinone prepared in Example 20 is listed as compound 104 in Table 1. Example 21 1-(4-BROMOMETHYL-2-CHLORO-5-ISOPROPOXYPHENYL)- 1 ,4-DIHYDRO-4-PROPYL-5H-TETRAZOL-5-ONE Under a dry nitrogen atmosphere, a stirred solution of 4.4 g (0.014 mole) of 1-(2-chloro-4-methyl-5-isopro- poxyphenyl ) -1 ,4-dihydro-4-propyl-5H-tetrazol-5-one (compound 91), 2.5 g (0.014 mole) of N-bromosuccinimide, and 0.06 g (0.00025 mole) of benzoyl peroxide in 80 mL of carbon tetrachloride was heated at reflux temperature for two days. The reaction mixture was allowed to cool to room temperature, filtered, and the filtrate washed with a saturated aqueous sodium chloride solution. The washed filtrate was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to leave an oil. The oil was crystal¬ lized from petroleum ether to yield 2.7 g of 1-(4-bromo- methyl-2-chlo o-5-isopropoxyphenyl)-1 ,4-dihydro-4- propyl-5H-tetrazol-5-one, mp 68-70'C. The nmr spectrum was consistent with the proposed structure. The tetrazolinone of Example 21 is listed as compound 107 in Table 1. 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), rice (Oryza sativa var. Labelle), wheat (Triticum aestivium var. Prodax), field bindweed (Convolvulus arvensis) , morningglory (Ipomea lacunosa or Ipo ea hederacea) , velvetleaf (Abutilon theophrasti) , barnyardgrass (Echinochloa crus galli) , green foxtail (Setaria viridis) , johnsongrass (Sorghum halepense) , and 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 O PI uniformly on top of each flat to a depth of approxi¬ mately 0.5 cm. The flats for the preemergence test were watered, then drenched with the appropriate amount of a solution of the test compound in a mixture of acetone and water containing a small amount (up to 0.5% v/v) of sorbitan monolaurate emulsifier/solubilizer. The concentration of the test compound in solution was varied to give a range of application rates, generally 8.0 kg/ha and submultiplies thereof. The flats were placed in a greenhouse and watered regularly at the soil surface for 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 foliage of the emerged test plants was sprayed with a solution of the test compound in acetone-water containing up to 0.5% sorbitan monolaurate. After spraying, the foliage 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 determined 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: Rating Description Percent of Main Crop Weed Control Categories Description Description 0 No effect No crop reduction No weed control or injury 10 Slight discoloration Very poor weed or stunting control 20 Slight Some discoloration, Poor weed effect stunting or stand loss control 30 Crop injury more Poor to defi¬ pronounced but not cient weed lasting control 40 Moderate injury, Deficient weed crop usually control recovers 50 Moderate Crop injury more Deficient to effect lasting, recovery moderate weed control 60 Lasting crop Moderate weed injury no recovery control 70 Heavy injury and Control somewhat stand loss less than satis¬ factory 80 Severe Crop nearly des¬ Satisfactory to troyed a few good weed survivors control 90 Only occasional Very good to live plants left excellent control 100 Complete Complete crop Complete weed effect destruction destruction O PI _ Herbicidal data at selected application rates are given for various compounds of the invention in Table 3 and 4 below. The test compounds are identified in the tables below by numbers which correspond to those in Table 1 above. In the tables of herbicidal data below: "kg/ha" is kilograms per hectare, "% K" is percent kill, and "% C" is percent control. it is clear that the generic class of aryltetra- zolinones and thiones described and illustrated herein is characterized by herbicidal activity, and that the degree of this activity varies among specific compounds within this class and to some extent among the species of plant to which these compounds may be applied. Thus, selection of a specific herbicidal compound for control of a specific plant may readily be made. For herbicidal application, the active compounds as above defined are formulated into herbicidal composi- tions 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, recognizing 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 applica¬ tion. 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 act as dispersants and carriers for the toxicant; these finely divided solids have an average particle size of less than about 50 microns. A typical 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 absorbent, readily wet inorganic diluents. Wettable powders 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 disper¬ sion. 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 ligno- sulfonate 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 post- emergence application to facilitate dispersion on the foliage and absorption by the plant. Other useful formulations for herbicidal applica¬ tions are emulsifiable concentrates. Emulsifiable concentrates are homogeneous liquid or past compositions 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 concentrates are dispersed in water or other liquid carrier, and normally applied as a spray to the area to be treated. The percentage by we.ight 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 composi¬ tion. Typical wetting, dispersing or emulsifying agents used in agricultural formulations include, for example, 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 composi¬ tion. Other useful formulations for herbicidal applica¬ tions include simple solutions of the active ingredient in a dispersant in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene or other organic solvents. Granu- lar formulations, wherein the toxicant is carried on relatively coarse particles, are of particular utility for aerial distribution or for penetration of cover crop canopy. Pressurized sprays, typically aerosols wherein the active ingredient is dispersed in finely divided form as a result of vaporization of a low boiling dispersant solvent carrier, such as the Freons, may also be used. Water-soluble or water-dispersible granules OMPI - are also useful formulations for herbicidal application of the present compounds. Such granular formulations are free-flowing, non-dusty, and readily water-soluble or water- iscible. This soluble or dispersible granu- lar formulations described in U.S. patent No. 3,920,442, incorporated herein by reference are useful herein with the present 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 selective 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 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-(methoxy- methyl)acetamide (alachlor), 2-chloro-N-(2-ethyl-6- methylphenyl)-N-( 2-methoxy-1-methylethyl)acetamide (metolachlor) , and N-chloroacetyl-N-(2,j6-diethylphenyl)- glycine (diethatyl-ethyl) ; benzothiadiazinone herbicides such as 3-(1-methylethyl)-(1H)-2,1 ,3-benzothiadiazin-4- (3H)-one-2,2-dioxide (bentazon); triazine herbicides such as 6-chloro-N-ethyl-N-( l-methylethyl)-1 ,3,5-tria- zine-2,4-diamine (atrazine), and 2-{ [4-chloro-6-(ethyl- amino)-1 ,3 ,5-triazin-2-yl] amino } -2-methylpropanenitrile (cyanazine) ; dinitrolaniline herbicides such as 2,6- dinitro-N ,N-dipropyl-4- ( trif luoromethyl ) benzene amine ( trif luralin) ; and aryl urea herbicides such as N ' - ( 3 , 4-dichlorophenyl ) -N ,N-dimethylurea ( diuron ) and N ,N-dimethyl-N' - [3- ( trif luoromethyl ) phenyl] urea ( fluo- meturon ) . OMPI IPO , It is apparent that various modifications may be made in the formulation and application of the compounds of this invention without departing from the inventive concepts herein as defined in the claims. - \3UEAtT OMPI . , IPO -Λ> X ATiO*ϊ Table 1 Representative Compounds Cpd No. _X_ • _ R W 1 Cl Cl Cl • n-C 3 H 7 0 2 CH=CH 2 0 2 Cl Cl Cl CH Table 1 (Continued) 24 Cl Cl O-n-C j R, n-C-H 0 25 α. Cl 0-n-C 3 H 7 CH 2 CH=CH 2 0 26 Cl Cl CCH(CH 3 ) 2 n- ^ 0 28 Br Br CCH(CH 3 ) 2 CH 2 CH=CH 2 0 29 Br Br OWCB.). OΪ 2 OCH 3 0 30 Cl l 0-n-C 4 H 5 ° rC Λ 0 31 Cl Cl OCH 2 CH 2 F n-CgBy 0 32 Cl Cl 0(CE 2 ) 2 CH 2 F ll-C j Hy 0 33 Cl Cl OCHF 2 n-C 3 H ? 0 36 Cl Br OCH(CH 3 ) 2 n-C 3 H ? 0 37 Cl Cl OCH 2 CK(CH 3 ) 2 n-C^ 0 38 l Cl OCH 2 CH 2 OH n-C 3 H 7 0 39 Cl Cl OCH 2 CH=CH 2 n-C 3 H ? 0 40 Cl Cl CCH 2 C(C1)=CH 2 n-C 3 H 7 0 41 Cl Cl OCH 2 CSCH CH 3 0 42 Cl Cl OCH 2 C=CH % 0 43 F F OCH j C≡CH C 2 H 5 0 44 Cl F CCH 2 C=CH Λ 0 45 Cl α OCH 2 C=CH n-CgHy 0 47 α F CCH j C≡CH ^^ 0 48 F Cl OCH 2 C=CH n-Cjϊi j 0 49 Cl Br CCH 2 C=CH n-C^ 0 50 Br Cl CCH 2 C=CH n-C 3 H ? 0 51 Cl Cl OCH 2 CΞCH CH(CH 3 ) 2 0 52 Cl Cl OCH 2 CΞCH -C^ 0 53 Cl Cl CCH 2 C=CH CH 2 CH(CH 3 ) 2 0 54 Cl OCH 2 C=CH HF 2 0 55 α Cl CCH -ΞCR W 0 Table 1 (Continued) 76 Cl Cl °-0 n-C 3 H ? 0 77 Cl Cl OCH 2 -^ n-C 3 H 7 0 78 Cl Cl •~ _- ι n-C 3 H 7 0 79 Cl Cl o - n-C 3 H 7 0 80 Cl Cl n-C 3 H 7 0 0 II 81 ci Cl 0-CCH 3 n-C 3 H 7 0 ^ i-^ ' u f OMPI \fλτ- 9 . WIPO . * ^NAT\ Q $ - 5 ' S - Table 1 (Continued) 82 Cl Cl oα_ 2 co 2 H n—C-jH-i 0 83 Cl Cl ocH 2 σo 2 <_H 3 n-C 3 H 7 0 84 Cl Cl OCH 2 C0 2 C 2 H 5 n-C 3 H 7 0 85 Cl Cl cα_2 sσϊ 3 n-GjB, 0 86 Cl Cl 0SO 2 CH 3 n-C 3 H 7 0 87 Cl Br 0SO 2 CH 3 n-C 3 H 7 0 88 Cl Cl 0SO 2 CH(CH 3 ) 2 n-C 3 H 7 0 89 Cl Cl OS0 2 CF 3 n-C 3 H ? 0 90 Cl α_ 3 oα_ 3 n-C 3 H 7 0 91 Cl CH 3 OCH(CH 3 ) 2 n-C^ 0 92 Cl 0CH 2 C3CH n-C 3 H ? 0 <*3 93 Cl CH 3 0(CH 2 ) 2 OC 2 H 5 n-C 3 H ? 0 94 Cl CF 3 OCH 3 n-C 3 H 7 0 95 CH 3 Cl CCH 3 n-C 3 H 7 0 96 CH 3 Cl OCH 3 CH 2 CH=CH 2 0 97 α_ 3 Cl oca 2 c≡zs n- 3 H ? 0 98 CH 3 Cl OCH 2 CΞCH CH 2 CH=CH 2 0 99 CH., Cl 0CH 2 0CH 3 n-C 3 H ? 0 3 100 Cl Cl OCH(CH 3 ) 2 CH(CH 3 ) 2 0 101 Cl OCH(CH 3 ) 2 CH 2 OCH 3 0 102 Cl Br °- n-C 3 H ? 0 103 Cl Br °^> n-C 3 H 7 0 104 Cl α OCH αι=α_ 2 0 105 Cl F oα_ 3 0 % 106 Cl F 0CH 3 n-C 3 H ? 0 107 Cl CH^r 0CH(CH 3 ) 2 n-C 3 H 7 0 108 Cl CF 3 OCH(CH 3 ) 2 n-C 3 H ? 0 109 Cl Cl H n-C 3 H 7 0 110 Cl Cl H CB(CH 3 ) 2 0 Table 1 (Continued) 112 Cl Cl H CH j SO^ 0 113 Cl Cl H (_H 2 CH-=CH 2 0 114 Cl Cl H CH 2 CN 0 115 F Cl OCH 2 C≡CI n-C 3 H 7 0 116 F Cl ' OCH 2 C≡CH C Λ 0 117 Cl Cl OCH—OC«H q (CH 2 ) 2 α_ 2 F 0 118 F Cl OCH 3 < Ά 0 119 Cl Cl OCH 2 C 6 H 5 CH 2 C(0)CH 3 0 .120 F Cl OCH 2 C 6 H 5 (CH 2 ) 2 CH 2 F 0 121 F Cl OCH 2 C=CH (CH 2 ) 2 CH 2 F 0 122 Cl Cl OCH 2 CBr=CHBr n-C 3 H ? 0 123 Cl Cl OCH 2 C 6 H 5 CH 2 CH 2 OH 0 124 Cl Cl 0CH(CH 3 )CO 2 C 2 H 5 n-C 3 H ? 0 125 F Br 0CH 2 C33_ n—CoH»— . 0 126 Cl Cl OCH(CH 3 )C0 2 C 2 H 5 (CH 2 ) 2 CH 2 F 0 127 Cl Cl 0C0 2 C 2 H 5 (CH 2 ) 2 CH 2 F 0 128 F Cl OCH(CH 3 )C0 2 C 2 H 5 (CH 2 ) 2 CH 2 F 0 129 Cl Cl OCH(CH 3 )C(0)CH 3 (CH 2 ) 2 CH 2 F 0 130 Cl Cl OCH(CH 3 )C0 2 CH(CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 131 Cl Cl OCH 3 CH 2 CH 2 C(0)H 0 132 Cl Cl OCH(CH 3 )C0 2 CH 2 CH 2 F (CH 2 ) 2 CH 2 F 0 133 F Cl oα_ 2 c=cι (CH 2 ) 2 CH 2 F 0 134 Cl Cl OCH(CH 3 )C0 2 CH 2 CF 2 (CH 2 ) 2 CH 2 F 0 135 Cl Cl OCH(CH 3 )C0 2 CH(CH 2 F) 2 (CH 2 ) 2 CH 2 F 0 136 Cl Cl OCH(CH 3 )CN (CH 2 ) 2 CH 2 F 0 137 F Cl OCH(CH 3 )C0 2 C(CH 3 ) 3 (CH 2 ) 2 CH 2 F 0 138 F Cl OCH(CH 3 )C0 2 CH(CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 139 F Cl CCH(CH 3 )CN (CH 2 ) 2 CH 2 F 0 140 F Cl 0CH(CH3)C0 2 CH(C 2 H 5 ) 2 (CH 2 ) 2 CH 2 F 0 141 F Cl 0CH 2C3 _H (CH 2 ) 2 CHF 2 0 142 F Cl OCH(CH 3 )C0 2 CH(CH 3 )CH(CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 Table 1 (Continued) 143 F Cl oα_(o_ 3 ) 2 H S 144 F Cl OH (CH 2 ) 2 CH 2 F o 145 Cl Cl OS0 2 CF 3 (CH 2 ) 2 CH 2 F 0 146 Cl Cl OCH 3 (CH 2 ) 2 CHF 2 0 17 Cl Cl N0 2 n- 3 H ? O 148 Cl Cl oα_ 3 C_H 2 CH 2 C(0)H s 149 Cl Cl OCH 3 (CH 2 ) 2 CHF 2 s 150 F . OCH 2 C 6 H 5 CH 2 CH 2 C(0)H 0 151 Cl Cl OCH(CH 3 ) 2 CH 2 CH 2 C(0)H s 152 F Cl OCH(CH 3 )C0 2 CH(CH 2 F) 2 (Oi 2 ) 2 CH 2 F 0 153 F Cl 0CH(CH 3 )CO 2 CH[CH(CH 3 ) 2 ] 2 (σ_2) 2 CH 2 F 0 154 F Cl OCH(CH 3 )00 2 N=C(CH 3 ) 2 (CH 2 ) 2 CH 2 F o 155 F Cl OCH 2 C 6 H 5 CΉ(CH 3 ) 2 0 156 F CL OCH(CH 3 ) 2 CH 2 CH 2 C(0)H s 157 F Cl OCH 2 CgH 5 ^3 0 158 F Cl OCH(CH 3 )C0 2 α_(CH 3 )C 2 H 5 (CH 2 ) 2 CH 2 F 0 159 F Cl OCH 2 C≡CH CH(CH 3 ) 2 0 160 F Cl OCH(CH 3 )C(0)NH 2 (CH 2 ) 2 CH 2 F 0 161 F Cl CCH-C≡CH ^3 0 162 F Cl CC^CgH,- n-C 3 H 7 0 163 Cl Cl OCH(CH 3 ) 2 n-C 3 E- 0 164 F Cl 0CH(CH 3 )CO 2 CH(CH 2 ) 3 CH 2 (CH 2 ) 2 CH 2 F o 165 F Cl OCH(C 2 H 5 )00 2 CH(CH 3 ) 2 (CH 2 )CH 2 F 0 166 F Cl CCH(O_ 3 )C0 2 CH(CH 3 )C=CH (CH 2 ) 2 CH 2 F o 167 F Cl OCH(.CH 3 )C0 2 C(CH 3 ) 2 C=CH (CH 2 ) 2 CH 2 F o 168 F Cl OCH 2 C-CH n-c^ o 169 F Cl OCH(CH 3 )C≡CH (CH 2 ) 2 CH 2 F 0 170 Cl Cl OCH(CH 3 )C≡CH n-C 3 H 7 0 171 F Cl OCH(CH 3 )C0 2 CH 2 CHCH 2 CH 2 (CH 2 ) 2 CH 2 F 0 172 F Cl OCH(CH 3 ) 2 (CH 2 ) 2 CHF 2 s 173 F Cl OCH 2 C * KH CH 2 CHFCH 3 0 174 F Cl OCH 2 C=CH (CH 2 ) 2 CHF 2 s Table 1 (Continued) 178 Cl OCH 2 C 6 H 5 CH 2 CHFCH 3 0 179 F Cl OCH(CH 3 )C0 2 H H 0 180 F Cl OCH 2 CgH 5 CH(CH 3 )C 2 H 5 0 181 F Cl OH CH(CH 3 )C 2 H 5 " 0 182 F Cl OCH(CH 3 )C0 2 H (CH 2 ) 2 CH 2 F 0 183 F Cl OCH(CH 3 )C0 2 CH(CH 2 OCH 3 ) 2 (CH 2 ) 2 CH 2 F 0 184 F Cl ocH(α_ 3 )oo 2 c 3 H 7 (CH 2 ) 2 CHF 0 185 F Cl 0CH 2 C3CH CH(α_ 3 )c 2 H 5 0 186 F Cl 0 2 H 0 187 F Cl H (CH 2 ) 2 CH 2 F 0 188 F Cl OCH(CH 3 )C0 2 C(CH 3 ) 2 CN (CH 2 ) 2 CH 2 F 0 189 F Cl 0 2 (CH 2 ) 2 CH 2 F 0 190 F Cl oα_ 2 ocH 3 (CH 2 ) 2 CH 2 F 0 191 F Cl NHC(0)N(O_ 3 ) 2 (CH 2 ) 2 CH 2 F 0 192 F Cl NHC(0)NHCH 2 CH(CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 0 195 F Cl N(S0 2 CH 3 ) 2 (CH 2 ) 2 CH 2 F O 196 F Cl OH CH 2 OCH 3 0 197 F Cl OCH 2 C 6 H 5 H 2 0CH 3 0 198 F ci OCH 2 C 6 H 5 CH 2 SCH 3 0 199 F Cl OCH(CH 3 )C(0)N(CH 2 CH=CH 2 ) 2 (CH 2 ) 2 CH 2 F 0 200 F Cl N(CH 2 CN)C(0)CH 3 (CH 2 ) 2 CH 2 F 0 201 F Cl N(C 2H 5 )C(0)O_3 (CH 2 ) 2 CH 2 F 0 202 F Cl NHC(0)CH 3 (CH 2 ) 2 CH 2 F 0 203 F Cl 0(CH 2 ) 2 0C 2 H 5 (CH 2 ) 2 CH 2 F 0 204 F 0CH(CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 Table 1 (Continued) Cpd NO. z R W 205 F Cl 0CH(CH 3 )CH 2 0CH 3 (CH 2 ) 2 α_ 2 F O 206 F Br OCH 2 C3CH (CH 2 ) 2 CH 2 F 0 208 F Cl oα-2sα_ 3 (CH 2 ) 2 CB 2 F 0 209 F Cl OCH(CH 3 )C0 2 C(CH 3 ) 2 C≡CH 0 ^ GH 2>2 CH 2 F 210 F Br ' OH (CH 2 ) 2 CH 2 F 0 211 F Br OCH 2 C 6 H 5 H 0 212 F Br OCH 2 C 6 H 5 (CH 2 ) 2 Cfl 2 F 0 213 F Cl OCH 2 C 6 H 5 SCF 3 0 214 F Cl OCH 2 C 6 H 5 CH 2 CN 0 215 F Cl (CH 2 ) 2 CH 2 F 0 CT 3 216 F Cl OCH^tO)^ (CH 2 ) 2 CH 2 F 0 218 Cl 1 (CH 2 ) 2 CH 2 F 219 F Cl 0(CH 2 ) 2 OCH 3 (CH 2 ) 2 CH 2 F O 220 F 0 2 CCH 2 C3_H (CH 2 ) 2 CH 2 F 0 221 F Cl 0CH(CH 3 )C(0)CH 3 (CH 2 ) 2 CH 2 F 0 222 F Cl OCH (CH 3 ) C ( CH 3 )=N-OH (CH 2 ) 2 CH 2 F 0 224 F Br OCH 2 OCH 3 (CH 2 ) 2 CH 2 F 0 229 F CH, oα_ 2 c≡CH (CH 2 ) 2 CH 2 F o - 230 F OCH(CH 3 )00 2 CH(CH 3 ) 2 ^3 (CH 2 ) 2 CH 2 F 0 231 F C 2H 5 0CH 2 C 6 H 5 (CH 2 ) 2 CH 2 F 0 232 F C 2 H 5 OH (CH 2 ) 2 CH 2 F 0 233 F CCH 2 C≡CH (CH 2 ) 2 CH 2 F 0 <_% 234 F C 2 H 5 0CH(CH 3 )CO 2 CH(CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 Table 1 (Continued) 236 F Cl OCH(CH 3 )C0 2 CH(CH 3 ) 2 OΪ 2 CF 2 CH 3 0 237 F Cl SCH 2 CN (CH 2 ) 2 CH 2 F 0 238 F Cl SCH 2 C=CH (CH 2 ) 2 CH 2 F 0 239 F Cl SCH(CH 3 )C0 2 CH(CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 240 F Cl N(CH 3 )(S0 2 CH 3 ) (CH 2 ) 2 CH 2 F 0 241 F Cl N(C 2 H 5 )(S0 2 OΪ 3 ) (CH 2 ) 2 CH 2 F 0 242 F Cl N(CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 243 F Cl N(C 2 H 5 ) 2 (CH 2 ) 2 CH 2 F 0 244 F Cl N(S0 2 CF 3 ) 2 (CH 2 ) 2 α_ 2 F 0 245 F Cl HC0 2 CH 3 (CH 2 ) 2 CH 2 F 0 246 F Cl ____*:_ _ (CH 2 ) 2 CH 2 F 0 247 F Cl NHCH(CH 3 )C0 2 C 2 H 5 (CH 2 ) 2 CH 2 F 0 248 F Cl NHCK 2 C0 2 C 2 H 5 (CH 2 ) 2 CH 2 F 0 250 F Cl N=C(0_ 3 ) 2 (CH 2 ) 2 CH 2 F 0 251 F Cl «», (CH 2 ) 2 CH 2 F 0 252 F Cl OCH(CH3)OCH3 (CH 2 ) 2 CH 2 F 0 253 F Cl OCH(CH 3 )S(0)CH3 (CH 2 ) 2 CH 2 F 0 o 255 F Cl 0CH(CH3)00N(CH3) 2 (CH 2 ) 2 CH 2 F 0 257 F Cl OCH(CH 3 )CONHS(O) 2 CH 3 (CH 2 ) 2 CH 2 F 0 258 CF 3 Cl OCH 2 C=CH (CH 2 ) 3 CH 2 F 0 259. F Cl OCSjCn (CH 2 ) 2 CH 2 F s 260 F Cl 0C(CH 3 ) 2 C=CH (CH 2 ) 2 CH 2 F 0 OMPI Table 1 (Continued) Cpd NO. z R W 261 F Cl 0CH 2 C3_H CH 2 CH=CHF 0 262 F Cl Q. (CH 2 ) 2 CH 2 F 0 263 F Cl C0 2 C 2 H 5 (CH 2 ) 2 CH 2 F 0 264 F Cl C0 2 H (CH 2 ) 2 CH 2 F 0 266 F Cl S0 2 N(C 2 H 5 ) 2 (GEL j J j CH jj P 0 267 F Cl SO^gH,. (CH 2 ) 2 CH 2 F 0 268 F Cl 0 S0 2 NH 2 (CH 2 ) 2 CH 2 F 269 F Cl CH(0C 2 H 5 ) 2 (CH 2 ) 2 CH 2 F 0 270 F Cl C(CH 3 ){0C 2 H 5 ) 2 (CH 2 ) 2 CH 2 F 0 271 F Cl CH 2 C=CH (CH 2 ) 2 CH 2 F 0 272 F Cl H (CH 2 ) 2 CH 2 F s 273 F Cl 0CH 2 C 6 H 5 H 0 274 Cl Cl 0CH 2 C=CH C_H 2 CH 2 0CHF 2 0 276 Cl Cl ∞2 n-C 3 H 7 0 277 Cl Cl NHC(0)CH 3 n-C 3 H ? 0 278 F Cl 0CH 2 C 6 H 5 (CH 2 ) 2 CHF 2 0 279 F Cl OH (CH 2 ) 2 CHF 2 0 280 Cl Cl oα_ 2 c≡CH (CH 2 ) 2 CHF 2 s 281 F Cl OH CH(CH 3 ) 2 0 282 F Cl OH ∞S 0 283 F Cl OH n-C 3 H 7 0 284 F Cl OCH 2 C 6 H 5 CH 2 CF 2 CH 3 0 285 F Cl OH C3J 2 CF 2 CH 3 0 286 F Cl OH (CH 2 ) 2 CH 2 F s 287 F Cl OH CH 2 CHFCH 3 0 288 F Cl 0CH 2 C0 2 C 2 H 5 (CH 2 ) 2 CH 2 F Q 289 F Cl H H 0 290 F Cl NCO (CH 2 ) 2 CH 2 F 0 291 F Cl OH CH 2 SCH 3 0 292 F Cl 0CH 2 C=CH CH2SCH 3 0 Table 1 (Continued) Cpd NO. z R W 293 F 0 s H 294 Cl Cl OCH 2 CsCH CH 2 CF 2 CH 3 0 295 F H F H 0 296 F Cl OCH 3 " H 0 297 F Cl OCH 2 C=CBr (CH 2 ) 2 CH 2 F 0 298 F Cl 0O_ 2 C0 2 Na (CH 2 ) 2 CH 2 F 0 299 F Cl OCH(CH 3 )C0 2 K (CH 2 ) 2 CH 2 F 0 300 F Cl 0CH(CH 3 )CO 2 NH 4 (CH 2 ) 2 CH 2 F 0 301 F Cl 00 2 Na (CH 2 ) 2 CH 2 F 0 302 F Cl S0 3 Na (CH 2 ) 2 CH 2 F 0 303 F Cl OCH(CH 3 )C0 2 H (CH 2 ) 2 CH 2 F 0 304 F • Cl OCH(CH )CH=CH 2 (CH 2 ) 2 CH 2 F 0 305 F Cl SCH(CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 306 F Cl SCHF 2 (CH 2 ) 2 CH 2 F 0 307 F Cl SCH 2 C=CI (CH 2 ) 2 CH 2 F 0 308 F Cl SCH 2 CF 3 (CH 2 ) 2 CH 2 F 0 309 F Cl SCH 2 OCH 3 (CH 2 ) 2 CH 2 F 0 310 F Cl SCH^O^ (CH 2 ) 2 CH 2 F 0 311 F Cl 0(CH 2 ) 2 F (CH 2 ) 2 CH 2 F 0 312 F Cl 0(CH 2 ) 2 Br (CH 2 ) 2 CH 2 F 0 313 F Cl 0SO 2 CH 3 (CH 2 ) 2 CH 2 F 0 314 F Cl 0SO CF 3 (CH 2 ) 2 CH 2 F 0 315 F Cl CS0 2 CH 2 CH(CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 316 F Cl QS0 2 CHC1 2 (CH 2 ) 2 CH 2 F 0 317 F Cl 0SO 2 CH 2 C 6 H 5 (CH 2 ) 2 CH 2 F 0 318 F Cl CS0 2 CH 2 CN (CH 2 ) 2 CH 2 F 0 319 F Cl 0SO 2 CH 2 C^H (CH 2 ) 2 CH 2 F 0 320 F Cl CSO^CCI (CH 2 ) 2 CH 2 F " 0 321 F Cl 0SO 2 NHCH 3 (CH 2 2 CH 2 F 0 322 F Cl OS0 2 (CH 2 ) 2 N(CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 323 F Cl OS0 2 ( CH 2 ) 2 SCH 2 CH=CH 2 (CH 2 ) 2 CH 2 F 0 324 F Cl 0SO 2 ( CH 2 ) 2 OCH 2 C__CH (CH 2 ) 2 CH 2 F 0 325 F Cl . 0SO 2 ( CH 2 ) 2 0CH 2 CO 2 CH 3 (CH 2 ) 2 CH 2 F 0 ^ * Q ' _. JL. Λ u '* _ DjsϊH___ [ /Λ . W ' IPO .r Table 1 (Continued) 326 F Cl CS0 2 (CH 2 ) 2 OCH 2 C0 2 H (CH 2 ) 2 CH 2 F 0 327 F Cl QS0 2 (CH 2 ) 2 OCH(CH 3 )C0 2 Na (CH 2 ) 2 CH 2 F 0 328 F Cl αso 2 (α_2 Ϊ2 . 3CHGH 3 ) CO 2 CH 3 (CH 2 ) 2 CH 2 F 0 329 F Cl SCH 2 C0 2 H (CH 2 ) 2 CH 2 F 0 330 F Cl SCT 2 CO-SCH 3 (CH 2 ) 2 CH 2 F 0 332 F Cl OCHF00 2 H (CH 2 ) 2 CH 2 F 0 333 F Cl SCH 2 C0 2 N=C(CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 334 F Cl 0CHFC0 2 N=C(SCH 3 ) (CH 3 ) (CH 2 ) 2 ca 2 F 0 335 F Cl OCH(CH 3 )C0 2 N=C(SCH 3 ) (CH 3 ) (CH 2 ) 2 CH 2 F 0 336 F Cl 0CH(CH 3 )CO 2 N=C(CH 3 ) (C 2 H 5 ) (CH 2 ) 2 CH 2 F 0 337 F Cl 0CH 2 O0 2 (CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 338 F Cl SCH(CH 3 )C(CH 3 )-^lOH (CH 2 ) 2 CH 2 F 0 339 F Cl OCH 2 C(CH 3 )=NOH (CH 2 ) 2 CH 2 F 0 340 F Cl SCH(CH 3 )C(CH 3 ) * =N-OCH 3 (CH 2 ) 2 OΪ 2 F 0 341 F Cl 0CH(O_ 3 )C(CH 3 )==N-0CH(CH 3 ) 2 (CH 2 ) 2 CH 2 F 0 342 F Cl SCH(CH 3 )COCH 3 (CH 2 ) 2 CH 2 F 0 343 F Cl 0CH 2 00CH 3 (CH 2 ) 2 CH 2 F 0 344 F Cl SCH 2 C0CH 3 (CH 2 ) 2 CH 2 F 0 345 F Cl N=C(SCH 3 )(CP 3 ) (CH 2 ) 2 CH 2 F 0 346 F Cl α>-5CH 3 (CH 2 ) 2 CH 2 F 0 347 F Cl C0NH 2 (CH 2 ) 2 CH 2 F 0 348 F Cl C0NHCH 3 (CH 2 ) 2 CH 2 F 0 349 F Cl 00N(C 2 H 5 ) 2 (CH 2 ) 2 CH 2 F 0 350 F Cl OONHCgHg (CH 2 ) 2 CH 2 F 0 351 F Cl 0C_H 2 C=CH SCF 3 0 352 F CH 2 F ∞-∞ (CH 2 ) 2 CH 2 F 0 Table 2 Characterizing Data Compound ESnpirical ε Ilemental Anε ilysis No. mp( β C) Formula C H N 1 89-90 C 10 H 9 Cl 3 4 O C 39.05 2.95 18.22 F 39.13 3.22 17.80 2 100-101 C 10 H 7 C1 3 N 4° C 39.31 2.31 18.34 F 40.38 2.64 18.33 3 114-115 C 9 H 7 C1 3 N 4°2 C 34.92 2.28 18.10 F 36.01 2.59 17.91 4 47-48 C 11 H 12 C1 2 N 4° C F 5 55-57 C 11 H 10 C1 2 N 4° C F 6 158-159 C 9 H 8 C1 2 4 0 2 C 39.29 2.93 20.37 F 39.35 3.14 20.30 7 99-100 C 10 H 10 C1 2 N 4°2 C 41.54 3.49 19.38 F 42.55 3.50 16.91 8 59-60 C 10 H 10 P 2°2 N 4 C F 9 86-87 C 11 H 12 C1 2 4°2 C 43.57 3.99 18.48 F 44.40 4.02 16.35 10 65-67 C 11 H 12 F 2 N 4°2 C F 11 60-62 C 11 H 12 C1EΪΪ 4°2 C F 12 89-90 C 11 H 12 ErClN 4°2 C 38.00 3.48 16.11 F 38.07 3.41 15.96 13 65-67 Cl l H 12 BrCl 4 0 2 C F 14 54-56 C 12 H 14 C1 2 N 4°2 C F 15 81-85 C^H^Cl^^ C F Table 2 Characterizing Data Compourid Empirical Elemental Analysis No. I ( * C> Formula C H N 16 58-59 C 45.444.45 17.66 C 12 H 14 C1 2 N 4°2 F 45.51 4.28 17.17 17 144-145 C 9 E 6 C1 2 F 2 N 4°2 C 34.75 1.95 18.01 F 34.97 2.14 18.01 18 110-111 C 10 H 9 C1 2 BN 4°2 C 39.11 2.95 18.24 F 39.10 2.90 18.18 19 80-81 C 41.14 3.45 17.44 F 41.39 3.36 16.64 20 107-108 C 11 H 10 C1 24°2 C 43.873.35 18.61 F 43.95 3.40 17.05 21 103-104 C 12 H 12 C1 2 N 4°2 C 45.73 3.84 17.78 F 45.99 3.85 15.99 22 108-109 C 11 H 12 C1 2 N 4°3 C 41.39 3.79 17.56 F 43.97 4.04 14.24 23 86-87 43.58 4.00 C 11 H 12 C1 2 N 4°2 C 18.48 F 43.51 4.02 18.28 24 oil 13 H 16 C1 2 K 4°2 C 47.14 4.87 16.91 F 47.40 4.94 15.75 25 85-86 C 13 H 14 C1 24°2 C 47.43 4.29 17.02 F 47.66 4.35 17.02 26 oil C 13 H 16 C1 2 N 4°2 C 47.14 4.87 16.91 F 47.77 4.99 15.05 27 oil 47.43 4.29 17.02 C 13 H 14 C1 2 N 4°2 C F 47.72 4.15 15.80 28 oil C 13 H 14 Br 2 N 4°2 C 37.343.38 13.40 F 37.51 3.48 13.32 29 94-95 C 12 H 14 Br 2 N 4°3 C 34.15 3.34 13.28 F 34.28 3.41 13.28 30 71-72 C 14 H 18 C1 2 4 0 2 C 48.79 5.26 16.23 F 50.48 5.91 16.71 OMPI ■ Table 2 Characteπzinσ Data Compound Empirical Ielemental Analysis No. π-p('C) Formula C H N 31 74-75 C 12 H 13 Cl 2 fN 4 0 2 C 43 .00 3.91 16 .72 F 42.93 3.84 16 .71 32 78-79 C 13 H 15 C1 2 FN 4 0 2 C 44 .71 4.33 16 .05 F 44 .72 4.28 15 .83 33 oil C C 11 H 10 C1 2 F 2 N 4°2 F 34 83-84 C 38 C 12 H 11 C1 2 F 3 N 4°2 .83 2.99 15 .10 F 38 .84 2.90 14 .99 35 77-78 C 13 H 16 F 2 N 4°2 C 52 .34 5.41 18 .77 F 52 .38 5.18 18 .71 36 49-50 C 13 H 16 ErClN 4°2 C 41 .56 4.29 14, .92 F 42 .02 4.22 14, .73 37 51-52 C 14 H 18 C1 24°2 C 48, .70 5.26 16, .23 F 48, .79 5.16 16. .09 38 87-88 C 12 H 14 C1 2 N 4°3 C 43, .26 4.24 16, .82 F 43. .63 4.29 16. .86 39 57-58 C 13 H 14 C1 2 N 4°2 C 47. .43 4.29 17. .02 F 47. .49 4.50 16. .86 40 56-57 C 13 H 13 C1 3 N 4 0 2 C 42. ,94 3.60 15. ,41 F 43. ,65 3.68 14. ,96 41 155 C 11 H 8 C1 2 N 4°2 C 44. ,17 2.69 18. ,73 F 44. ,33 2.88 18. 55 42 120-121 C 12 H 10 C1 2 N 4°2 C 46. ,03 3.22 17. 89 F 46. 60 3.20 16. 37 43 71-72 C 12 H 10 F 2 N 4°2 C 51. 43 3.59 19. 99 F 51. 74 3.47 19. 95 44 88-89 C 12 H l0 ClN 4 O 2 C 48. 58 3.39 18. 88 F 48. 70 3.37 18. 90 45 70-72 C C 13 H 12 C1 24°2 F Table 2 Characterizing Data Compound Eirpirical E lemental Analysis No. mp( β C) Formula C H N 46 oil C 13 H 12 P 2 N 4°2 C F 47 72-73 C 13 H li ClF V4 C 50.25 3.89 18.03 F 50.21 3.79 17.97 48 60-62 - C 13 H 12 C1EN 4°2 C F 49 87-88 C l 3 H 12 BrClN 4 0 2 C 42.01 3.26 15.08 F 41.94 3.34 14.96 50 70-71 C 13 H 12 BTC1 4 0 2 C F 51 120-121 C 13 H 12 C1 2 N 4 0 2 C 47.72 3.70 17.12 F 47.67 3.32 16.70 52 73-74 C 14 H 14 α 2 N 4 0 2 C 49.27 4.14 16.42 F 50.04 3.94 15.07 53 90-91 C 14 H 14 C1 2 N 4 0 2 C 49.28 4.14 16.42 F 49.22 3.96 15.65 54 63-65 C 11 H 6 α 2 F 2 N 4 0 2 C F 55 118-120 C 12 H 9 C1 2 FN 4 0 2 C 44.53 2.69 16.69 F 43.52 2.74 16.92 56 86-87 Λi A C 45.54 3.15 16.05 F 45.23 3.21 16.23 57 oil C 13 H 11 BrCl 2 N 4°2 C 38.44 2.73 13.80 F 39.40 2.83 13.03 58 115-116 C 12 H 8 C1 2 4°2 C 46.24 2.59 17.98 F 47.12 2.83 16.93 59 127-128 C 12 H 10 Cl 2 N 4 O 3 C 43.79 3.06 17.02 F 44.42 3.01 17.03 60 79-80 C 13 H 12 C1 2 N 4 0 3 C 45.50 3.52 16.32 F 45.84 3.18 17.07 Table 2 Characterizing Data Compound Empirical E .lement.__l Analysis NO. mpCC) Formula C H N 61 134-138 34.46 2.45 12. C 13 H 11 C1 2 IN 4°2 C 37 F 34.85 2.46 12.37 62 58-60 C 14 H 14 C1 2 N 4°2 C F 63 oil C 12 H 11 C1 2 N 5°2 C 43.92 3.38 21.34 F 43.48 3.37 19.09 64 oil C 13 H 13 C1 2 5°2 C 45.63 3.82 20.46 F 45.66 3.72 20.10 65 oil C 15 H 17 C1 2 N 5°2 C F 66 112-113 C 11 H 12 C1 2 N 4°3 C 41.39 3.79 17.56 F 42.09 3.81 17.35 67 76-77 C 43.26 4.23 16.82 C 12 H 14 C1 2 N 4°3 F 43.73 3.97 16.82 68 oil C 12 H 14 P 4 N 4°3 C 47.99 4.70 18.66 F 48.21 4.72 18.08 69 oil C C 12 H 14 C1EΪI 4°3 F 70 72-73 C 38.16 3.74 14.84 C 12 H 14 BrClN 4°3 F 38.14 3.88 14.95 71 60-61 C C 13 H 16 C1 2 N 4°3 44.90 4.64 16.13 F 45.20 4.52 15.89 72 - C 12 H 13 C1 2 EN 4 C 3 C 41.04 3.73 15.96 F 35.44 3.12 11.49 73 60-61 C 14 H 18 C1 2 N 4°3 C 46.42 5.29 15.47 F 46.44 4.93 15.06 74 63-64 C 14 H 13 BrClN 4°3 C 41 .45 4.47 13.81 F 41.47 4.56 13.71 75 87-88 C 14 H 16 C1 2 N 4°3 C 46.81 4.49 15.60 F 46.95 4.39 15.60 Table 2 Characterizing Datat Compound Empirical Elemental Analysis No. mp( * C) Formula C H N 76 89-90 C 46.81 C 14 H 16 C1 2 N 4°3 4.49 15.60 F 47.0C 4.20 15.44 77 81-82 C 15 H 18 C1 2 N 4°3 C 48.26 4.86 15.01 • F 48.47 4.84 15.06 78 99-101 44.81 C 14 H 16 C1 2 N 4°4 C 4.30 14.93 F 44.93 4.32 14.58 79 83-84 48.27 4.86 15.01 C 15 H 18 C1 2 N 4°3 C F 48.44 4.85 14.78 80 oil C C 15 H 18 C1 24°4 F 81 91-92 C 12 H 12 C1 2 N 4°3 C 43.52 3.65 16.91 F 43.58 3.76 16.83 82 134-136 C C 12 H 12 C1 2 N 4°4 F 83 76-78 C C 13 H 14 C1 2 K 4°4 F 84 80-81 C 14 H 16 C1 2 N 4°4 C 44.81 4.30 14.93 F 45.45 4.22 13.48 85 58-59 C 12 H 14 C1 2 N 4°2 S C 41.28 4.04 16.05 F 41.63 3.86 16.07 86 64-65 C 11 H 12 C1 2 N 4°4 S C 35.98 3.29 15.25 F 36.37 3.28 14.55 87 75-76 C 11 H 12 BrClN 4 0 4 S C 32.09 2.94 13.61 F 32.15 2.84 13.59 88 60-61 C 13 H 16 C1 2 N 4°4 S C 39.50 4.08 14.17 F 39.76 4.00 13.98 89 52-53 C 11 H 9 C1 2 F 3 N 4°4 S C 31.37 2.15 13.31 F 31.76 2.13 13.38 90 74-75 C 12 H 15 C1N 4°2 C 50.975.35 19.82 F 51.04 5.40 19.77 ΓRE-AΪ OMPI • Table 2 Characterizinσ Data Ccmpound Empirical E " lemental Analysis No. mp( β C) Formula C H N 91 67-68 C 54.106.16 18.03 C 14 19 C1N 4°2 F 54.39 6.22 17.95 92 89-90 C 14 H 15 C1N 4°2 C 54.81 4.93 18.27 F 54.70 4.97 18.15 93 50-51 C. 5 H 2 .C1N 4 0 3 C 52.86 6.21 16.44 F 53.20 6.33 16.29 94 82-83 42.8 C 12 H 12 C1P 34°2 C 1 3.59 16.63 F 42.05 3.42 16.02 95 59-60 C 12 H 15 C1N 4 0 2 C F 96 65-66 C 12 H 13 C1 4°2 C F 97 100-101 • C 14 H 15 C1N 4°2 C F 98 129-130 C C 14 H 13 C1N 4°2 F 99 oil C C 13 H 17 C1N 4°3 F 100 oil C 13 H 16 C1 2 N 4°2 C 47.14 4.87 16.91 F 48.144.84 15.01 101 68-69 C 12 H 14 C1 2 N 4°3 C 43.26 4.24 16.81 F 43.68 4.36 16.31 102 170-171 41.66 3.99 13.87 C 14 fl 16 BrClN 4°3 C F 41.663.79 13. " 69 103 83-84 C 43.134.34 13.41 C 15 K 18 BrC1N 4°3 F 43.124.04 13.25 104 142-143 C 10 H 8 C1 2 N 4°2 C 41.832.81 19.51 F 41.70 2.72 19.51 105 79-80 C 10 H 10 C1FN 4°2 C F Table 2 Characterizing Data Ccmpound Empirical E lemental Analysis No. π-p('C) Formula C H N 106 85-86 C 11 H 12 C1E1Ϊ 4°2 C F 107 68-70 C u H T8 BrClN 4 0 2 C F 108 oil C 1 4 H 16 C1F 3 N 4 0 2 C 46.10 4.41 15.35 F 45.33 4.41 14.12 109 40-41 C C 10 H 10 C1 2 N 4 0 43.95 3.69 20.52 F 44.42 3.84 20.34 110 58-59 C C 10 l0 α 2 N 4° 43.95 3.69 20.52 F 43.64 3.69 20.37 111 116-1 17 C C 9 H 8 C1 2 N 4 0 2 39.27 2.93 20.37 F 39.29 2.90 20.45 112 99-100 C 9 H 8 C1 2 N 4 0S C 37.12 2.77 19.24 F 37.15 2.82 18.96 113 49-50 C C 10 H 8 C1 2 N 4° 44.30 2.97 20.66 F 44.73 3.07 20.50 1 14 121-122 C 9 H 5 C1 2 N 5 0 C 40.02 1.87 25.93 F 40.28 1.79 25.98 115 104-105 C^H^CIFIN^ C 35.76 2.54 12.83 F 38.87 3.03 12.84 116 90-91 C C 12 H 10 C1EN 4°2 48.58 3.40 18.89 F 49.30 3.49 18.80 117 45-46 C C 13 E 15 C1 2 N 4°3 F 42.75 4.15 15.34 F 43.37 4.30 15.85 118 70-72 C l 0 H 10 ClEN 4 O 2 C F 1 19 154-155 C C 17 H 14 C1 2 4°3 F 120 78-79 C 17 H 15 αF 2 N 4°2 C F OMPI _ Table 2 Characterizing Data Compound Empirical 1 Elemental Analysis No. p( β C) Formula C H N 121 49-51 C 13 H 11 C1F 2 N 4°2 C 47.50 3.38 17.04 F 47.85 3.38 16.40 122 64-65 C 13 H 12 Br 2 Cl 2 N 2°2 C 32.06 2.48 11.51 F 31.93 2.53 11.27 123 117--118 C 16 H 14 C1 2 N 4°3 C F 124 oil C 15 H 18 C1 2 N 4 0 4 C 46.28 4.67 14.39 F 48.50 5.49 11.68 125 oil C 13 H 12 BrfN 4 0 2 C F 126 oil C 15 H 17 C1 2 FN 4 0 4 C 44.24 4.21 13.76 F 46.66 4.87 12.32 127 oil C 13 H 13 C1 Λ 0 4 C 41.18 3.46 14.78 F 41.70 3.52 14.53 128 oil C 15 H 17 C1F 2 N 4°4 C 46.10 4.64 14.34 F 46.95 4.16 13.65 129 oil C 14 H 15 C1 Λ 0 3 C 44.58 4.01 14.85 F 44.89 3.93 14.05 130 oil C 16 H 19 C1 2 FN 4°4 C 45.62 4.55 13.30 F 45.95 4.56 12.98 131 73-74 C 11 H 10 C1 2 N 4°3 C 41.66 3.18 17.67 F 42.10 3.25 16.87 132 oil C 15 H 16 α 2 F 2 N 4°4 C 42.37 3.79 13.18 F 42.97 4.10 10.89 133 120-123 c 13 H l 0 F 2 iN 4 o 2 C 34.12 2.20 12.24 F 34.96 2.35 11.78 134 oil c 15 H 14 2 F 2 o 4 N 4 C 39.06 3.06 12.14 F 39.43 2.99 11.26 135 oil C 16 H 17 C1 2 F 3 N 4 0 4 C 42.03 3.75 12.25 F 41.90 3.59 11 .60 Table 2 Characterizing Data Goπpound Empirical Elemental Analysis No. mp( β C) Formula C H N C l3 H 12 α 2 ra 5°2 C 43.353. 36 19.45 F 43.423.14 18.30 137 oil 'iΛ i αF 2 N 4°4 C 48.755.06 13.38 F 48.555.01 12.52 138 oil C 47.474. C 16 H 19 C1F 2 N 4°4 74 13.84 F 47.734.69 13.48 139 oil C 13 H 12 C1F 2 N 5 0 2 C 45.423.52 20.37 F 47.423.88 18.90 140 oil Aa^A C 49.945.36 12.94 F 50.645.75 12.28 141 44-47 C C 13 H 10 C1F 3 N 4°2 F 142 oil : IΛ3 CIP A O 4 C 49.945. 36 12.94 F 49.655, 26 12.54 143 134-135 o^o 01 ^ 08 C F 144 83-85 C C 10 H 9 C1F 2 N 4°2 F 145 oil C 11 H 8 C1 2 F 4 N 4°4 S C 30.08 1. 84 12.76 F 30.89 1 , 89 12.49 146 81-82 C 11 H 10 C1 2 F 2 K 4°2 C F 147 77-78 C 10 H 9 α 2 N 5°3 C F 148 80-83 C 11 H 10 C1 2 N 4°2 S C F F 150 83-84 C 17 H 14 αF 4°2 C F ^ l ή ^ Table 2 Characterizing Data Compound Empirical Elemental Analysis No. mp( 'C) Formula C H N 151 oil C 15 H 17 C1 2 N 3 0 2 S C F 152 oil C 16 H 17 C1F 4 N 4 0 4 C 43.60 3.88 12.70 F 44.72 3.90 12.08 153 oil c 20 H 27 αF 2 N 4 o 4 C 52.11 5.91 12.16 F 52.76 5.83 11.37 154 oil C 16 H 18 C1F 2 N 5°4 C 46.00 4.34 16.79 F 46.70 4.26 15.37 155 oil C 17 H 16 C1F 4 0 2 C F 156 oil C 13 H l4 α 4°2 S C F 157 93-95 c l 5 H 12 αEN 4 o 2 C F 158 oil C 17 H 21 C1F 2 N 4°4 C 48.74 5.05 13.38 F 48.57 4.76 13.10 159 oil C 13 H 12 C1F 4°2 C 160 oil C 13 H 14 C1F 2 N 5°3 C F 161 137-138 c 1 7 H 8 αEN 4 o 2 C 46.74 2.85 19.82 F 47.14 2.93 19.77 F 163 52-54 C 14 H 16 C1 2 N 4°3 C F 164 oil C 18 H 2i αF 2 N 4°4 C 50.18 4.91 13.00 F 52.44 5.27 11.26 165 oil C 17 H 21 C1F 2 N 4 0 4 C 48.74 5.05 13.38 F 49.10 5.26 13.20 Table 2 Characterizing Data Compound Empirical E lemental Analysis No. πp('C) Formula C H N 166 oil C 49.22 4.13 C 17 H 17 C1F 2 N 4°4 13.51 F 49.49 4.02 13.19 167 oil C 18 H. 9 C1F2N 4 0 4 C 50.41 4.47 13.07 F 53.62 4.68 10.98 168 58-59 C 14 H 14 C1BN 4 0 2 C 51.78 4.35 17.25 F 51.91 4.41 17.22 169 78-79 C 14 H 13 C1F 2 N 4°2 C F 170 80-81 C 14 H 14 C1 2 N 4°2 C 49.28 4.14 16.42 F 49.45 4.19 16.59 171 oil C 17 H 19 C1F 2 N 4°4 C 48.98 4.60 13.44 F 49.38 4.51 12.71 172 oil C 13 H 14 ClF 3 N 4 OS C F 173 oil C 13 H 1 1 C1F 2 4 0 2 C 47.50 3.37 17.05 F 47.80 3.35 16.32 174 86-87 c 13 H 10 ciF 3 N 4 ns C 43.04 2.78 15.45 F 43.71 2.98 15.56 175 oil C 43.78 C 16 H 18 C1F 3 N 4°3 S 4.14 12.77 F 44.19 4.07 12.07 176 154-156 C H 14 ClEN 4 0 3 C 54.19 3.75 14.87 F 55.15 3.75 13.83 177 95-97 o^W 6 C - F 178 oil C 17 H 15 C1F 2 N 4 0 2 C F 179 122-123 C 10 H 8 C1 ^4°4 C F 180 68-70 C 18 H 18 C1BN 4 0 2 C F Table 2 Characterizing Data Compound Empirical Ielemental Analysis No. mp( β C) Formula C H N 181 102-105 C C 11 H 12 C1FN 4°2 F 182 oil C 13 H 13 C1F 2 N 4°4 C F 183 oil C 18 H 23 C1F 2 K 4°6 C 46,51 4.98 12.05 F 48.035.09 12.02 184 oil C 16 H 19 C1F 2 N 4°4 C 47.47 4.92 13.84 F 47.46 4.77 13.65 185 oil C 14 H 14 C1E* 4 0 2 C 51.784.35 17.25 F 50.794.39 16.55 186 157-158 C 7 H 3 C1FN 5 0 3 C F 187 62-63 C 10 H 9 ClF 2 4 O C F 188 oil C 17 H 18 C1F 2 N 5°4 C 47.50 4.22 16.29 F 47.57 4.05 15.48 189 80-81 C C 10 H 8 C1F 2 N 5°3 F 190 oil C C 12 H 13 C1P 2 N 4°3 F 191 oil C 15 H 19 C1F 26°2 C 46.33 4.93 21.61 F 46.59 4.85 21.32 192 132-134 C 15 H 19 C1F 2 N 6°2 C 46.334.93 21.61 F 46.434.85 21.45 193 115-116 C 12 H 10 C1EN 4°3 C 46.09 3.22 17.92 F 46.643.10 17.68 194 oil C C 18 H 16 C1F 2 N 5°3 F 195 92-94 C 12 H 14 C1F 2 5 0 5 S 2 C F Table 2 Characterizing Data Ccrrpound Empirical E, lemental Analysis No. mp( β C) Formula C H N 196 130-131 C C 9 F 8 C1FN 4°3 F 197 oil C C 16 H 14 C1BN 4°3 F 198 67-68 C 16 H 14 C1FN 4 0 2 S C F 199 oil C 19 H 22 C1F 2 N 5 0 3 C 51.64 5.01 15.84 F 49.12 4.55 14.44 200 113-115 C C 14 H 13 C1F 2 N 6°2 F 201 oil C 14 H 16 C1F 2 N 5°2 C F 202 112-113 C C 12 H 12 C1F 2 N 5°2 F 203 oil C C 14 H 17 C1F 2 N 4°3 46.35 4.72 15.45 F 46.65 4.65 15.30 204 oil C C 13 H 15 C1F 2 K 4°2 46.92 4.54 16.84 F 47.10 4.23 16.50 205 oil C 14 H 17 C1F 2 N 4°3 C 46.35 4.72 15.44 F 46.25 4.36 15.15 206 75-76 C 13 H π BrF 2 N 4 0 2 C 41.84 2.96 15.01 F 42.03 2.89 14.70 207 81-84 C C 10 H 10 C1F 2 N 5° F 208 66-67 c 12 H 13 F 2 N 4 o 2 s C F 209 oil Λθ∞VΛ C 45.68 4.05 11.84 F 45.98 4.20 11 .37 21C 121-122 C 10 H 9 ErF 2 N 4°2 C F OMPI Table 2 Characterizing Data Compound Eirpirical I Slemental Analysis No. πp( * C) Formula C H N 211 171-172 C 14 H 10 ErM 4°2 C F 212 84-86 C 17 H 15 BrF 2 N 4°2 C F 213 75-76 C 15 H 9 C1F 4 N 4°2 C F 214 111-112 C 16 H 11 C T 5°2 C F 215 44-45 C 11 H 11 C1F 2 K 4° C F 216 oil C 39.30 3.57 15.28 C 12 H 13 C1F 2 4°3 S F 40.07 3.89 13.94 217 oil C 10 H 8 F 3 N 5°3 C 39.61 2.66 23.10 F 39.55 3.09 21.27 218 oil C 46.60 4.19 15.53 C 14 H 15 C1F 2 N 4°3 F 46.30 3.97 14.91 219 69-70 C 44.77 4.34 16.07 C 13 H 15 C1F 2 N 4°3 F 44.78 4.24 16.08 220 oil C 13 H 11 C1F 2 N 5°4 C 46.02 3.27 20.64 F 45.59 3.45 20.85 221 oil C 46.61 4.19 15.53 C 14 H 15 C1F 2 N 4°3 F 46.41 4.15 15.31 222 100-106 C 14 H 16 C1F 2 N 5°3 C 44.63 4.28 18.59 F 44.51 4.38 17.70 223 81-82 C 44.71 4.19 18.72 C 14 H 17 C1 2 N 5°4 F 44.93 4.58 18.72 224 oil C 38.01 3.46 14.77 C 12 H 13 ErF 2 N 4°3 F 37.76 3.30 14.34 225 78-80 C 14 H 13 BrF 2 N 4°2 C F 226 oil C 1Q H 9 F 3 N 4 0 C F tTable 3 Preemergence Herbicidal . Activity Compound No. 1 2 3 4 5 6 Rate (kg/ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % K % K % K % K % K % K Cotton 0 0 0 0 0 0 Soybean 0 0 0 0 0 0 Field Corn - — - 0 0 - Rice 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 Field Bindweed - - 0 0 - - Morningglory 0 0 0 0 0 0 Velvetleaf 100 100 100 80 80 90 Barnyardgrass 0 0 0 25 0 0 Green Foxtail 90 95 90 85 60 100 Johnsongrass 0 0 0 90 40 0 Yellow Nutsedge ™• <-_-> 0 0 ~* Ccmpound No. 7 8 9 10 11 12 Rate Og/ha) 4.0 4.0 4.0 4.0 0.25 4.0 Species % K % K % K % K % K % K Cotton 0 0 0 0 0 0 Soybean 0 100 60 50 0 0 Field Corn - 0 - - 0 0 Pice 10 100 100 90 30 - Wheat 20 100 0 100 20 - Field Eindweed - 100 - - 0 50 Morningglory 0 0 0 0 0 0 Velvetleaf 100 100 100 100 100 100 Barnyardgrass 70 100 20 100 80 100 Green Foxtail 100 100 100 100 95 100 Johnsongrass 90 100 95 100 50 95 Yellow Nutsedge - 20 - - 0 0 -grTEUSA . OMPI . vfy, IΪO Table 3 (Continued) <_e_npound No. 13 14 15 16 17 18 Rate (kg ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % K % K % K % K % K % K Cotton _ 0 0 0 0 0 Soybean - 0 0 0 0 0 Field Corn - 0 100 - - 60 Rice 30 0 0 - 0 0 Wheat 20 100 100 - 0 90 Field Bindweed - 0 0 - - 0 Morningglory - 0 0 0 0 0 Velvetleaf 100 0 100 100 100 100 Barnyardgrass 95 0 80 0 0 0 Green Foxtail 100 0 100 100 90 100 Johnsongrass 100 0 90 95 60 40 Yellow Nutsedσe 100 0 0 — - 0 Compound No. 19 20 21 22 23 24 Pate (kg/ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % K % K % K % K % K % K Cotton 40 0 0 0 0 0 Soybean 80 0 0 0 0 60 Field COrn 100 - - - - - Rice 60 30 20 95 0 95 Wheat 100 0 30 85 0 80 Field Bindweed 0 - - - - - Morningglory 40 0 0 20 0 0 Velvetleaf 100 100 100 100 75 100 Barnyardgrass 100 0 0 0 0 100 Green foxtail 100 100 100 100 95 100 Johnsongrass 90 95 85 10 40 100 Yellow Nutsedge 50 - - - - - Table 3 (Continued) Ccmpound No. 25 26 27 28 29 30 Rate ( g/ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % K % % K % K % K % K Cotton 20 0 0 0 0 50 Soybean 10 0 0 0 0 0 Field Corn - - 75 - - - Rice 0 20 0 0 0 0 Wheat 10 70 20 0 0 0 Field Bindweed - - 0 - - - Morningglory 0 0 0 0 0 70 Velvetleaf 90 100 100 80 80 90 Barnyardgrass 0 90 100 0 0 60 Green Foxtail 90 100 100 100 95 100 Jo__nsongrass 20 70 100 0 0 50 Yellow Nutsedge - - 0 - - - Ccmpound No. 31 32 33 34 35 36 Rate (kg/ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % K % K % K % K % K % K Cotton ' 0 0 0 C 30 0 Soybean 20 0 0 0 30 20 Field Corn 0 60 - 40 0 - Rice 10 0 20 0 100 0 Wheat 100 90 20 50 95 40 Field Bindweed 0 0 - 0 20 - Morningglory 0 0 100 0 0 0 Velvetleaf 100 80 100 100 100 100 Barnyardgrass 90 90 60 80 100 100 Green Foxtail 100 100 100 100 95 100 Johnsorigrass 90 90 100 95 30 100 Yellow Nutsedge 0 30 — 30 100 — Table 3 (Continued) Compound No. 37 38 39 40 41 42 Rate (kg ha) 4.0 4.0 4.0 4.0 4.0 0.25 Species % K % K % K % K % K % K Cotton 0 0 0 0 0 0 Soybean 0 0 0 0 0 0 Field Corn - 0 - 0 60 0 Rice 0 0 20 0 90 0 . ■" heat 0 0 0 70 100 0 Field Bindweed - 100 - 20 70 0 Morningglory 0 50 0 0 0 0 Velvetleaf 90 0 100 90 100 100 Barnyardgrass 40 0 40 90 100 0 Green Foxtail 100 50 100 100 100 90 Johnsongrass 20 0 95 60 100 90 Yellcw Nutsedσe 0 0 — 0 0 0 Compound No. 43 44 45 46 47 48 49 Rate (kg/ha) 0.25 4.0 0.25 0.25 4.0 0.25 0.25 Species % K % K % K % K % K % K % K Cotton 0 0 0 0 0. 0 0 Soybean 0 30 0 0 0 0 0 Field Corn 30 30 0 50 30 30 - Rice 30 100 - 40 100 90 0 Wheat 0 30 - 0 100 80 0 Field Bindweed 0 100 0 40 90 80 - Morningglory 0 0 0 0 0 0 0 Velvetleaf 100 100 100 100 100 100 100 Barnyardgrass 80 100 20 50 100 100 60 Green Foxtail 95 100 95 100 100 100 100 Johnsongrass 30 95 50 100 100 100 30 Yellcw Nutsedge 0 10 0 20 90 0 - OMPI Table 3 (Continued) Confound NO. 50 51 52 53 54 55 Rate (kg ha) 0.25 0.25 4.0 4.0 2.0 4.0 Species % R % K % K % K % K % K Cotton 0 0 0 0 0 0 Soybean 10 0 20 0 0 70 Field Corn 0 0 30 60 100 30 Rice 0 0 0 10 50 10 Wheat 0 0 100 0 90 10 Field Bindweed 0 0 70 0 85 60 Morningglory 0 0 20 20 10 50 Velvetleaf 95 100 100 100 100 100 Barnyardgrass 90 40 0 80 100 95 Green Foxtail 100 50 100 100 100 100 Johnsongrass 10 100 30 100 100 100 Yellow Nutsedge 0 0 0 0 10 0 Compound No. 56 57 58 59 60 61 Rate (kg ha) 0.25 4.0 4.0 4.0 4.0 4.0 Species % K % K % K % K % K % K Cotton 0 0 0 20 0 0 Soybean 0 0 0 30 20 0 Field COrn 0 0 0 30 0 90 Rice 0 0 30 90 0 90 Wheat 0 0 0 80 0 20 Field Bindweed 0 0 20 100 0 50 Morningglory 0 0 0 90 0 0 Velvetleaf 100 100 100 100 100 100 Barnyardgrass 100 0 100 90 50 100 Green Foxtail 100 70 100 100 100 100 Johnsongrass 100 20 90 100 100 100 Yellow Nutsedge 0 0 0 40 0 30 Table 3 (Continued) Coπpound No. 62 63 64 65 66 67 Rate (kg ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % K % K % K % K % R % R Cotton 0 0 0 0 0 0 Soybean 0 0 0 0 0 60 Field Corn 0 0 - 0 75 0 Rice 0 - 80 0 90 - heat 0 - 100 0 100 - Field Bindweed 0 0 - 0 0 100 Morningglory 0 30 20 20 0 20 Velvetleaf 100 20 100 100 100 100 Barnyardgrass 10 0 60 90 100 95 Green Foxtail 95 30 100 100 100 100 Johnsongrass 80 0 95 100 100 80 Yellow Nutsedge 0 0 - 0 75 40 Conipound No. 68 69 70 71 72 73 Rate (kg/ha) 0.25 0.25 4.0 4.0 4.0 4.0 Species % K % R % R % R % R % R Cotton 0 0 0 0 0 0 Soybean 0 0 90 0 0 0 Field Corn 0 60 - 0 0 0 Rice 0 90 90 0 0 - Wheat 0 60 100 0 0 - Field Bindweed 0 80 - 0 0 100 Morningglory 0 0 0 0 0 20 Velvetleaf 100 100 100 20 80 100 Barnyardgrass 90 100 100 95 0 40 Green Foxtail 90 100 100 100 95 100 Johnsongrass 30 90 100 90 0 40 Yellow Nutsedge 0 0 0 0 0 / ^ s^ t OMPI Table 3 (Continued) Ccmpound No. 74 75 76 77 78 79 Pate (kg ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % R % R % R % R % R % R Cotton 0 0 0 0 0 0 Soybean 0 0 0 0 0 0 Field Corn - - 0 - - 0 Rice 0 0 0 0 95 0 Wheat 60 0 0 30 100 0 Field Bindweed - - 0 - - 0 Morningglory 30 100 0 0 20 0 Velvetleaf 100 80 0 100 100 0 Barnyardgrass 0 0 0 0 95 0 Green Foxtail 100 40 0 95 100 0 Johnsongrass 10 90 0 0 50 0 Yellow Nutsedge - — 0 — — 0 Ccmpound No. 80 81 82 83 84 85 Rate (kg/ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % K % K % K % K % R % R Cotton 0 0 0 50 0 0 Soybean 0 0 0 20 0 40 Field Corn 75 - 0 0 - - Rice 0 0 0 0 0 25 Wheat 0 0 0 0 0 10 Field Bindweed 0 — 0 80 - - Morningglory 0 0 0 60 20 100 velvetleaf 100 100 40 100 0 100 Barnyardgrass 25 0 0 0 0 65 Green Foxtail 100 0 0 70 0 95 Johnsongrass 100 0 0 0 0 100 Yellow Nutsedσe — — 0 0 — — Table 3 (Continued) Compound No. 86 87 88 89 90 91 Rate (kg/ha) 4.0 4.0 4.0 4.0 4.0 Species % R % R % K % K % R % R Cotton 0 0 0 0 0 0 Soybean 0 0 0 0 0 0 Field Corn - - - - - - Rice 0 0 0 0 30 10 Wheat 60 30 0 0 0 0 Field Bindweed - - - - - - Morningglory 70 70 0 0 0 0 Velvetleaf 100 100 100 100 90 30 Barnyardgrass 50 100 100 0 0 90 Green Foxtail 100 100 100 90 0 100 Johnsongrass 100 100 95 0 10 80 Yellow Nutsedge - - - - - - Compound No. 92 93 94 95 96 97 Rate (kg/ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % R % K % K % K % K % K Cotton 0 0 0 0 0 0 Soybean 0 0 0 0 0 60 Field Corn - - 80 0 0 0 Rice 20 0 0 20 10 50 Wheat 40 0 40 0 0 30 Field Bindweed - - 0 0 0 60 Morningglory 0 0 0 0 0 70 Velvetleaf 100 100 100 100 100 100 Barnyardgrass 100 0 50 50 0 100 Green Foxtail 100 30 100 100 100 100 Johnsongrass 100 0 60 90 0 100 Yellow Nutsedge — — 0 0 0 0 ' SLEXtr' OMPI Table 3 (Continued) Compound No. 98 99 100 101 102 103 Rate (kg ha) 2.0 2.0 4.0 8.0 4.0 4.0 Species % R % R % R % R % R % R Cotton 0 0 0 0 0 0 Soybean 20 20 0 0 0 0 Field Corn 0 35 0 0 0 0 Rice 10 75 0 0 0 0 Wheat 10 90 0 0 0 0 Field Bindweed 10 0 0 0 0 0 Morningglory 0 0 0 0 0 0 Velvetleaf 10 80 60 50 0 0 Barnyardgrass 95 70 0 0 0 0 Green Foxtail 100 100 50 0 0 75 Johnsongrass 60 50 60 0 0 0 Yellow Nutsedge 0 0 0 0 0 0 Compound No. 104 105 106 107 108 109 Rate (kgTa) 4.0 4.0 4.0 2.0 4.0 8.0 Species % R % R % R % R % R % R Cotton 0 0 0 0 0 _. Soybean 0 0 0 0 0 0 Field Corn 0 0 0 0 0 0 Rice 0 0 0 0 0 - Wheat 0 0 0 0 0 0 Field Bindweed 0 0 0 30 0 0 Morningglory 0 0 0 0 0 0 Velvetleaf 90 95 100 0 0 100 Barnyardgrass 0 0 0 0 0 100 Green Foxtail 90 0 80 0 100 100 Johnsongrass 0 0 0 30 0 95 Yellow Nutsedge 0 0 0 0 0 - Table 3 (Continued) Compound No. no 111 112 113 114 115 Rate (kg ha) 8.0 8.0 8.0 8.0 8.0 4.0 Species % R % R % R % R % R % R Cotton _ _ * _> _ 100 Soybean 30 0 0 0 0 100 Field Corn 30 100 0 0 0 100 Rice - - - - - 100 Wheat 0 0 0 0 0 100 Field Bindweed 0 0 0 0 0 100 Morningglory 0 - - - - 100 Velvetleaf 100 100 50 40 90 100 Barnyardgrass 20 100 0 0 0 100 Green Foxtail 100 95 80 10 0 100 Johnsongrass 40 - 0 - - 100 Yellow Nutsedge - - - - - 100 Compound No. 116 117 118 119 120 121 Rate (kg ha) 2.0 4.0 8.0 8.0 8.0 2.0 Species % R % K % K % R % K % C Cotton 100 0 100 0 0 100 Soybean 100 100 100 0 0 100 Field Corn 100 100 100 0 30 100 Rice 100 90 - - - 100 Wheat 100 100 100 0 0 100 Field Bindweed 100 70 100 0 0 100 Morningglory 100 70 100 0 0 100 Velvetleaf 100 100 100 0 0 - Barnyardgrass 100 100 100 0 0 100 Green Foxtail 100 - 100 0 0 100 Johnsongrass 100 100 100 0 0 100 Yellow Nutsedge 100 20 100 Table 3 (Continued) Ccmpound NO. 122 123 124 125 126 127 Rate (kg ha) 8.0 8.0 4.0 ~ " ΪTθ 4.0 2.0 Species % C % C % C % C % C % C Cotton 0 0 40 80 60 10 Soybean 0 0 10 100 0 10 Field Corn 0 0 0 90 30 10 Rice 0 - 40 80 40 20 heat 0 0 20 80 40 0 Field Bindweed 0 0 60 70 80 10 Morningglory 0 0 100 100 100 30 Velvetleaf 0 0 100 100 100 10 Barnyardgrass 30 0 90 100 80 20 Green Foxtail 40 0 100 100 100 70 Johnsongrass 30 0 70 100 100 10 Yellow Nutsedge 0 — 20 80 50 10 Compound NO. 128 129 130 131 132 133 Rate (kg ha) 2.0 2.0 4.0 8.0 2.0 2.0 Species % C % C % C % C % C % C Cotton 100 30 100 100 50 100 Soybean 10 20 10 70 20 100 Field Corn 30 100 50 30 40 100 Rice 90 70 80 - 70 100 Wheat 90 70 80 40 60 100 Field Bindweed 100 40 100 100 100 100 Morningglory 100 20 100 100 90 100 Velvetleaf 100 100 100 60 100 100 Barnyardgrass 100 100 100 0 90 100 Green Foxtail 100 100 100 100 100 100 Johnsongrass 100 90 100 80 80 100 Yellow Nutsedge 90 20 90 40 100 Table 3 (Continued) Ccmpound No. 134 135 136 137 138 139 Rate (kg ha) 2.0 2.0 2.0 2.0 2.0 2.0 Species % C % C % C % C % C % C Cotton 80 40 20 80 100 100 Soybean 20 0 30 20 10 100 Field Corn 20 0 80 80 70 100 Rice 70 40 90 100 100 100 Wheat 60 40 80 80 100 90 Field Bindweed 100 100 90 100 100 100 Morningglory 80 80 100 90 100 100 Velvetleaf 80 90 100 100 100 100 Barnyardgrass 80 50 100 100 100 100 Green Foxtail 100 100 100 100 100 100 Johnsonσrass 30 90 100 100 100 100 Yellow Nutsedge 50 10 30 100 100 100 Compound No. 140 141 142 143 144 145 Rate (kg/ha) 2.0 0.125 2.0 8.0 4.0 8.0 Species % C % C % C % C % C % C Cotton 100 30 100 0 60 10 Soybean 10 30 20 0 60 • 0 Field Corn 70 80 50 0 90 40 Rice 100 80 100 - 70 - Wheat 100 20 90 0 100 0 Field Bindweed 100 40 100 0 90 0 Morningglory 100 50 100 0 50 70 _ Velvetleaf 100 100 100 0 100 90 Barnyardgrass 100 100 100 0 90 90 Green Foxtail 100 90 100 0 100 100 Johnsongrass 100 60 100 0 80 90 Yellow Nutsedge 100 50 100 30 Table 3 (Continued) Compound No. 146 147 148 149 150 151 Rate (kg ha) 8.0 8.0 8.0 8.0 8.0 8.0 Species % C % C % C % C % C % C Cotton 50 20 0 40 0 0 Soybean 100 50 0 70 0 0 Field Corn 90 20 30 90 0 0 Rice - - - - - - Wheat 100 0 0 40 0 0 Field Bindweed 100 0 0 80 0 0 Morningglory 100 50 0 90 0 0 Velvetleaf 100 90 0 100 0 0 Barnyardgrass 100 40 0 100 0 0 Green Foxtail 100 50 0 100 0 0 Johnsongrass 100 0 0 100 0 0 Yellow Nutsedge - - - - - - Compound No. 152 153 154 157 158 159 Rate (kg ha) 1.0 1.0 2.0 8.0 8.0 8.0 Species % C % C % C % C % C % C Cotton 100 20 100 20 100 90 Soybean 10 10 20 0 80 100 Field Corn 10 0 30 0 90 100 Rice 90 0 90 - - - Wheat 70 0 90 0 90 100 Field Bindweed 100 90 100 10 100 100 Morningglory 90 20 100 60 100 100 Velvetleaf 100 90 100 60 100 100 Bamyardgrass 100 90 100 50 100 100 Green Foxtail 100 100 100 80 100 100 Johnsongrass 90 20 100 20 100 100 Yellcw Nutsedge 90 0 90 - - - Table 3 (Continued) Compound No. 160 161 162 163 164 165 Rate (kg ha) 1.0 8.0 153 Species % C % C % c % c % c % C Cotton 90 100 20 30 80 80 Soyhean 70 100 10 50 10 10 Field Corn 90 100 0 90 0 80 Rice 90 - - - 100 80 Wheat 90 100 0 50 80 80 Field Bindweed 100 100 20 100 100 60 Morningglory 100 100 30 70 80 60 Velvetleaf 100 100 30 100 100 100 Barnyardgrass 100 100 20 100 100 100 Green Foxtail 100 100 80 100 100 100 Johnsongrass 100 100 0 90 90 60 Yellow Nutsedge 90 - — — 60 80 Compound No. 166 167 168 169 170 171 Pate (kg/ha) 8.0 8.0 1.0 0.125 1.0 1.0 Species % C % c % c % C % c % c Cotton 100 100 20 40 10 100 Soybean 90 90 50 40 10 60 Field Corn 90 90 80 90 70 10 Rice - - 70 80 30 100 Wheat 100 90 40 80 40 100 Field Bindweed 100 100 10 100 0 100 Morningglory 100 100 30 80 10 90 Velvetleaf 100 100 100 100 90 100 Barnyardgrass 100 100 70 100 90 100 Green Foxtail 100 100 100 100 100 100 Johnsongrass 100 100 70 100 90 90 Yellow Nutsedge 40 50 10 90 OMPI ^^ Table 3 (Continued) Compound No. 172 173 174 175 176 177 Rate (kg ha) 0.5 0.125 0.5 1.0 8.0 8.0 Species % C % C % C % C % C % C Cotton 20 10 20 20 0 70 Soyhean 20 40 90 50 0 90 Field Corn 40 70 60 0 0 90 Rice 60 80 70 70 - - Wheat 20 40 40 90 0 70 Field Bindweed 30 30 100 100 0 40 Morningglory 10 0 100 60 0 70 Velvetleaf 100 100 100 100 0 100 Earnyardgrass 90 100 100 80 0 90 Green Foxtail 100 100 100 100 0 90 Johnsongrass 80 90 90 100 0 70 Yellow Nutsedge 40 30 30 70 — — Ccarpound No. 178 179 180 181 182 183 Pate (kg ha) 8.0 4.0 8.0 8.0 2.0 1.0 Species % C % C % C % C % C % C Cotton 20 60 0 20 100 100 Soybean 50 20 0 40 20 20 Field Corn 90 10 0 60 70 20 Rice - 80 - 0 100 90 Wheat 70 50 0 30 90 80 Field Bindweed 20 100 0 40 100 100 Morningglory 80 90 20 10 90 90 _ Velvetleaf 100 100 10 30 100 100 Barnyardgrass 90 100 80 80 100 100 Green Foxtail 100 100 90 90 100 100 Johnsongrass 50 90 80 40 100 100 Yellow Nutsedge 60 100 90 OMPI A^ IPO Λ, Table 3 (Continued) Ccmpound No. 184 185 186 187 188 189 Rate (kg/ha) 1.0 1.0 8.0 0.5 1.0 1.0 Species % C % C % C % C % C % C Cotton 100 20 0 0 100 10 Soybean 20 20 0 30 0 0 Field Corn 40 80 0 90 10 0 Rice 100 80 - 70 90 10 Wheat 90 70 0- 70 70 10 Field Bindweed 100 30 0 30 100 0 Morningglory 100 60 0 50 100 10 Velvetleaf 100 100 0 100 100 70 Barnyardgrass 100 100 0 100 90 40 Green Foxtail .100 100 0 100 100 30 Johnsongrass 100 90 0 90 100 10 Yellow Nutsedge 90 20 40 90 0 Compound No. 190 191 192 193 194 195 Rate (kg/ha) 0.25 1.0 1.0 1.0 1.0 1.0 Species % C % C % C % C % C % C Cotton 80 40 10 90 0 100 Soybean 70 30 0 100 60 50 Field Corn 100 100 10 100 10 100 Rice - 60 0 100 0 - Wheat 100 90 10 100 10 90 Field Bindweed - 50 0 90 0 - Morningglory 50 90 0 90 60 100 _ Velvetleaf 100 100 80 100 60 100 Barnyardgrass 100 60 0 100 70 100 Green Foxtail 100 90 0 100 0 100 Johnsongrass 100 90 50 100 0 80 Yellow Nutsedge 90 60 0 90 0 90 Table 3 (Continued) Compound No. 196 197 * 198 199 200 201 Rate (kg/ha) 8.0 8.0 8.0 0.5 2.0 2.0 Species % C % C % C % C % C % C Cotton 50 10 10 0 30 90 Soybean 40 0 0 10 50 90 Field Corn 40 70 50 60 70 100 Rice - - - 10 20 90 Wheat 80 70 70 40 20 100 Field Eindweed 60 90 60 50 20 60 Morningglory 40 60 80 10 10 20 Velvetleaf 100 100 90 90 10 100 Barnvardσrass 90 100 90 30 10 100 Green Foxtail 90 100 100 70 50 100 Johnsongrass 70 90 90 60 10 70 Yellow Nutsedge - — — 20 10 50 Cαrpound NO. 202 203 204 205 206 207 Rate (kg/ha) 2.0 0.5 0.5 0.5 0.25 4.0 Species % C % C % C % C % C % C Cotton 20 80 40 60 90 50 Soybean 60 70 70 40 90 90 Field Corn 0 90 80 90 90 20 Rice 20 90 90 90 70 20 Wheat 10 90 70 90 60 30 Field Eindweed 10 100 100 100 100 30 Morningglory 10 100 90 100 90 30 Velvetleaf 90 100 * 100 100 100 100 Barnyardgrass 0 100 100 100 100 40 Green Foxtail 0 100 100 100 100 10 Johnsongrass 0 90 100 100 100 40 Yellow Nutsedσe 0 70 40 60 60 20 OMPI WIFO ^ Table 3 (Continued) Compound No. 208 209 210 211 212 213 Rate (kg ha) 0.5 1.0 8.0 4.0 8.0 8.0 Species % C % C % C % C % C % C Cotton 50 50 0 0 0 0 Soybean 40 20 0 0 0 0 Field Corn 50 40 100 0 0 . 0 Rice 40 90 - 0 - - Wheat 40 50 0 0 0 0 Field Bindweed 100 100 0 0 0 0 Morningglory 50 90 0 0 0 0 Velvetleaf 100 100 0 0 0 0 Barnyardgrass 100 100 0 0 0 0 Green Foxtail 100 100 0 0 0 90 Johnsongrass 90 90 0 0 0 0 Yellow Nutsedσe 40 70 — 0 — — Compound No. 214 215 216 217 218 219 Rate (kg/ha) 8.0 8.0 2.0 8.0 0.5 0.5 Species % C % C % C % C % C % C Cotton 0 100 100 30 90 80 Soybean 0 100 90 20 80 60 Field Corn 0 100 100 40 100 100 Rice - 80 100 - 90 80 Wheat 0 100 100 40 100 90 Field Bindweed 0 100 100 0 100 80 Morningglory 0 100 100 0 100 100 Velvetleaf 0 100 100 90 100 100 Barnyardgrass 40 100 100 40 100 100 Green Foxtail 0 100 100 0 100 100 Johnsongrass 60 100 100 70 100 100 Yellow Nutsedσe — 100 90 — 90 90 OMPI Table 3 (Continued) C ipound No. 220 221 222 223 224 225 Rate (kg/ha) 2.0 TO " ' 1.0 1.0 0.5 0.5 Species % C % C % C % C % C % C Cotton 70 90 60 10 80 90 Soybean 40 80 60 0 70 100 Field Corn 80 100 100 20 100 100 Rice 50 95 50 10 95 90 Wheat 70 95 80 0 100 95 Field Bindweed 20 100 90 0 100 100 Morningglory 50 95 80 20 100 100 Velvetleaf 100 100 100 40 100 100 Barnyardgrass 90 100 95 10 100 100 Green Foxtail 90 100 95 0 100 100 Johnsongrass 90 100 70 0 100 95 Yellow Nutsedge 40 70 40 0 95 70 Table 4 Postemergence Herbicidal Activity Compound NO. 4 5 8 9 11 12 Rate (kg ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % R % R % K % K % K % R Cotton 90 30 50 50 100 30 Soybean 0 0 0 0 100 0 Field Corn 0 0 0 0 100 0 Rice 0 0 0 0 100 0 Wheat 0 0 0 0 100 0 Field Bindweed 0 0 0 80 100 0 Morningglory 0 0 0 0 100 0 Velvetleaf 100 100 100 100 100 100 Parnyardgrass 0 0 0 0 100 0 Green Foxtail 20 80 0 40 100 80 Johnsongrass 0 0 0 0 100 0 Yellow Nutsedge 0 0 0 0 60 0 "7 Compound No. 14 15 18 19 20 21 Rate ( σ/ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % R % R % R % K % K % K Cotton 60 20 60 100 0 80 Soybean 0 0 0 0 0 0 Field Corn 0 0 0 0 0 0 Rice 0 0 0 20 0 0 Wheat 0 0 0 0 0 0 Field Bindweed 0 0 20 70 40 0 Morningglory 0 0 0 30 0 0 Velvetleaf 100 100 100 100 100 100 Barnyardgrass 0 0 0 10 0 0 Green Foxtail 0 0 0 100 80 60 Johnsongrass 0 0 70 90 0 0 Yellow Nutsedge 0 0 0 0 0 0 Table 4 Postemergence Herbicidal Activity Cαrpound NO. 24 27 - 28 31 32 34 Rate (kg ha) 4.0 4.0 4.0 4.0 4.0 Species % R % R % R % K % R % R Cotton 100 0 50 90 70 60 Soybean 0 0 0 10 0 0 Field Corn 0 0 0 0 0 0 Rice 0 0 0 30 0 0 Wheat 0 0 0 0 0 0 Field Bindweed 0 0 0 20 0 95 Morningglory 0 0 0 80 0 20 Velvetleaf 90 95 0 10Q 100 100 Barnyardgrass 0 0 0 90 0 0 Green Foxtail 0 0 0 95 95 95 Johnsongrass 0 0 0 100 50 50 Yellow Nutsedge 0 0 0 0 0 0 Compound No. 35 36 37 38 40 41 Pate (kg/ha) 4.0 4.0 4.0 4.0 4.0 Species % R % K % K % K % K % K Cotton 100 100 20 100 70 0 Soybean 0 0 0 0 0 0 Field Corn 0 0 0 0 0 0 Rice 30 0 0 0 0 0 Wheat 0 0 0 0 0 0 Field Bindweed 95 50 0 50 90 0 Morningglory 50 0 0 20 30 0 Velvetleaf 100 100 100 100 100 60 " Barnyardgrass 40 85 20 0 0 0 Green Foxtail 90 40 70 90 100 0 Johnsongrass 60 65 0 0 10 0 Yellow Nutsedge 40 0 0 0 0 0 Table« 4 Postemergence Herbicidal Activity Compound No. 42 43 44 45 47 48 Rate (kg ha) 4.0 4.0 4.0 2.0 4.0 4.0 Species % K % R % K % K % R % R Cotton 65 100 100 80 100 100 Soybean 0 30 IP 0 10 100 Field Corn 0 40 0 0 0 100 Rice 40 . 95 0 50 30 100 Wheat 0 - 0 40 - 100 Field Bindweed 65 100 80 90 0 100 Morningglory 90 100 90 80 100 100 Velvetleaf 100 100 100 100 100 100 Barnyardgrass 100 100 100 70 80 100 Green Foxtail 90 90 100 100 100 100 Johnsongrass 100 100 80 100 100 100 Yellcw Nutsedge 0 - 0 0 0 90 Compound No. 49 51 52 53 54 55 Rate (kg/ha) 4.0 4.0 4.0 4.0 " TJS 4.0 Species % K % K % K % K % K % K Cotton 100 100 100 100 50 40 Soybean 0 50 G 10 0 0 Field Corn 0 30 0 0 0 0 Rice 0 30 0 0 0 0 Wheat 0 - 80 0 0 0 Field Bindweed 0 100 60 90 85 100 Morningglory 60 90 20 100 30 80 Velvetleaf 100 100 100 100 100 100 Barnyardgrass 20 95 0 70 10 50 Green Foxtail 0 100 90 100 70 90 Johnsongrass 80 100 10 100 100 95 Yellow Nutsedge 0 0 0 0 0 0 Table 4 Postemergence Herbicidal Activity Compound No. 56 57 58 59 60 61 Rate (kg ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % R % R % R % R % R % R Cotton 100 100 90 100 100 100 Soybean 80 0 0 0 0 0 Field Corn 100 0 0 0 0 0 Rice 40 0 0 0 0 0 Wheat 100 0 0 0 0 0 Field Bindweed 100 100 0 0 0 100 Morningglory 100 100 0 0 10 0 Velvetleaf 100 100 100 100 90 100 Barnyardgrass 100 0 0 0 0 100 Green Foxtail 100 30 90 95 0 100 Johnsongrass 100 0 0 50 70 100 Yellow Nutsedσe 40 0 0 0 0 50 Compound No. 65 66 68 69 70 71 Rate (kg/ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % K % K % K % K % R % K Cotton 100 10 100 100 90 60 Soybean 0 0 0 100 0 10 Field Corn 0 0 0 100 0 0 Rice 0 10 0 100 0 0 Wheat 0 0 0 100 0 0 Field Bindweed 20 30 50 100 30 30 Morningglory 50 50 40 100 30 80 Velvetleaf 100 100 100 100 100 100 Barnyardgrass 80 70 0 100 90 30 Green Foxtail 20 65 100 100 20 30 Johnsongrass 80 10 0 100 30 0 Yellow Nutsedge 0 0 0 100 0 0 Table 4 Postemergence Herbicidal Activity Compound No. 72 73 " 74 76 78 79 Rate (kg/ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % R % R % K. % K % R % R Cotton 10 0 10 50 60 90 Soybean 0 0 0 0 0 0 Field Corn 0 0 0 0 0 0 Rice 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 Field Bindweed 100 0 0 40 0 50 Morninqglory 10 0 10 50 0 0 Velvetleaf 60 0 100 100 0 100 Barnyardgrass 0 0 0 0 0 0 Green Foxtail 0 0 0 0 0 0 Johnsongrass 0 0 0 0 0 0 Yellow Nutsedge 0 0 0 0 0 0 Compound No. 80 84 87 88 94 95 Pate (kg/ha) 4.0 4.0 4.0 4.0 4.0 4.0 Species % K % K % K % K % K % R Cotton 95 60 30 60 0 85 Soybean 0 0 0 0 0 0 Field Corn 0 0 0 0 0 0 Rice 0 0 0 0 0 10 Wheat 0 0 0 0 0 0 Field Bindweed 10 70 0 30 90 35 Morningglory 10 0 20 0 0 20 Velvetleaf 100 20 100 100 90 100 Barnyardgrass 20 0 25 50 0 0 Green Foxtail 20 0 10 65 0 10 Johnsongrass 20 0 0 40 40 0 Yellow Nutsedσe 0 0 0 0 0 0 Table 4 Postemergence Herbicidal Activity Corπpound NO. 96 97 115 116 117 118 Rate (kg ha) - 4.0 4.0 4.0 2.0 4.0 8.0 Species % R % R % R % R % R % R Cotton 85 10 100 100 80 100 Soybean 0 0 40 100 40 100 Field Corn 0 0 100 100 100 100 Rice 0 0 100 100 30 - Wheat 0 0 100 100 60 100 Field Bindweed 50 0 100 100 90 100 Morningglory 0 0 100 100 70 100 Velvetleaf 100 100 100 100 100 100 Barnyardgrass 0 90 100 100 90 100 Green Foxtail 0 60 100 100 - 100 Johnsongrass 0 90 100 100 100 100 Yellow Nutsedge 0 0 100 100 0 - Compound NO. 119 120 121 122 123 124 Rate (kg/ha) 8.0 8.0 2.0 8.0 8.0 4.0 Species % R % R % C % C % C % C Cotton 0 100 100 30 20 100 Soybean 0 10 100 10 20 30 Field Corn 0 30 100 0 30 40 Rice - - 100 0 - 90 Wheat 0 10 100 0 10 20 Field Bindweed 0 90 100 70 10 100 Morningglory 0 90 100 0 20 100 _. Velvetleaf 0 100 - 50 20 100 Barnyardgrass 0 100 100 30 20 100 Green Foxtail 0 100 - 0 70 100 Johnsongrass 0 100 100 0 20 30 Yellow Nutsedge 100 10 0 Table 4 Postemergence ' Herbicidal Activity Compound No. 125 126 127 128 129 130 Rate (kg ha) 1.0 4.0 2.0 2.0 2.0 4.0 Species % C % C % C % C % C % C Cotton 100 100 100 100 100 100 Soybean 100 40 0 60 30 50 Field Corn 100 30 0 100 30 20 Rice 100 100 0 100 60 20 Wheat 90 70 0 100 10 30 Field Bindweed 100 100 10 100 100 100 Morningglory 100 100 10 100 100 100 Velvetleaf 100 100 100 100 100 100 Barnyardgrass 100 90 10 100 20 90 Green Foxtail 100 100 90 100 100 100 Johnsongrass 100 80 0 100 40 80 Yellow Nutsedge 70 30 0 80 0 30 Compound No. 131 132 133 134 135 136 Rate (kg/ha) 8.0 2.0 2.0 2.0 2.0 2.0 Species % C % C % C % C % C % C Cotton 0 100 100 100 100 70 Soybean 20 60 100 40 40 50 • Field Corn 0 10 100 40 0 90 Rice - 60 100 10 20 30 Wheat 0 20 100 30 40 90 Field Bindweed 0 100 100 100 100 100 Morningglory 0 80 100 80 90 80 Velvetleaf 0 100 100 100 100 100 - Barnyardgrass 0 80 100 90 90 80 Green Foxtail 0 100 100 100 100 100 Johnsongrass 0 10 100 50 90 80 Yellow Nutsedge 10 100 0 10 50 Table 4 Postemergence Herbicidal Activity Garpound No. 137 138 * 139 140 141 142 Rate (kg ha) 2.0 2.0 2.0 2.0 0.125 2.0 Species % C % C % C % C % C % C Cotton 100 100 100 100 100 100 Soybean 20 50 100 20 50 50 Field Corn 60 40 100 50 30 90 Rice 100 100 100 90 40 100 heat 90 100 100 100 10 100 Field Bindweed 100 100 100 100 80 100 Morningglory 100 90 100 100 80 100 Velvetleaf 100 100 100 100 100 100 Barnyardgrass 100 100 100 100 70 100 Green Foxtail 100 100 100 100 90 100 Johnsongrass 100 100 100 100 10 90 Yellcw Nutsedge 80 70 100 60 20. 80 Ccmpound NO. 143 144 145 146 147 148 Rate (kg ha) 8.0 4.0 8.0 8.0 8.0 8.0 Species % C % C % C % C % C % C Cotton 30 100 90 90 20 10 Soybean 10 40 30 70 20 30 Field Corn 20 60 60 90 20 20 Rice 70 - - - - Wheat 20 80 20 80 10 10 Field Bindweed 10 90 20 30 0 0 Morningglory 20 90 50 100 20 20 Velvetleaf 20 100 100 100 30 20 Barnyardgrass 0 100 20 90 0 10 Green Foxtail 50 90 70 70 0 0 Johnsongrass 0 70 20 80 0 0 Yellow Nutsedge - 10 - - - - 9 MEAlT OMPI " _ Table 4 Postemergence Herbicidal Activity • Compound No. 149 150 151 152 153 154 Rate (kg ha) 8.0 8.0 8.0 1.0 1.0 2.0 Species % C % C % C % C % C % C Cotton 80 40 20 100 100 100 Soybean 40 20 30 30 30 50 Field Corn 40 20 20 30 20 50 Rice - - - 100 20 100 Wheat 30 10 10 100 20 100 Field Bindweed 80 0 10 100 90 100 Morningglory 60 50 20 100 90 100 Velvetleaf 100 50 20 100 100 100 Barnyardgrass 20 0 10 100 70 100 Green Foxtail 100 10 10 100 100 100 Johnsongrass 80 0 10 40 40 100 Yellow Nutsedge - - - 30 20 90 Compound No. 155 156 157 158 159 160 Rate (kg/ha) 8.0 8.0 8.0 8.0 1.0 Species % C % C % C % C % C % C Cotton 100 80 40 100 100 100 Soybean 70 60 30 100 100 70 Field Corn 70 30 20 100 100 30 Rice - - - - - 90 Wheat 20 10 0 100 100 40 Field Bindweed 100 20 0 100 100 100 Morningglory 100 80 20 100 100 90 Velvetleaf 100 90 90 100 100 100 Barnyardgrass 100 - 0 100 100 100 Green Foxtail 100 40 20 100 100 100 Johnsongrass 90 40 20 100 100 100 Yellow Nutsedge 40 Table 4 Postemergence Herbicidal Activity Conpound NO. 161 162 163 164 165 166 Rate (kg ha) 8.0 8.0 8.0 0.5 1.0 Species % C % C % C % C % C % C Cotton 100 60 80 100 100 100 Soybean 100 30 40 50 40 80 Field Corn 100 0 30 60 40 90 Rice - - - 80 60 - Wheat 100 20 40 80 70 100 Field Bindweed 100 20 90 90 100 100 Morningglory 100 20 50 90 100 100 Velvetleaf 100 90 100 100 100 100 Barnyardgrass 100 0 60 60 100 - Green Foxtail 100 - - 100 100 100 Johnsongrass 100 20 40 30 40 100 Yellow Nutsedge - - - 50 10 - Conpound NO. 167 168 169 170 171 172 Rate (kg ha) 8.0 1.0 0.125 1.0 1.0 0.5 Species % C % C % C % C % C % C Cotton 100 80 100 100 100 100 Soybean 70 20 80 50 50 60 Field Corn 100 30 30 50 10 90 Rice - 80 50 40 100 40 Wheat 100 30 70 30 90 60 Field Bindweed 100 20 90 100 100 90 Morningglory 100 100 100 90 90 50 Velvetleaf 100 100 100 100 100 100 Barnyardgrass - 80 50 40 100 90 Green Foxtail 100 40 100 100 100 90 Johnsongrass 100 30 50 40 50 80 Yellow Nutsedge - 10 30 20 60 30 OMPI - Ill - Table 4 Postemergencei Herbicidal Activity Compound No. 173 174 * 175 176 177 178 Rate (kg ha) 0.125 0.5 1.0 8.0 8.0 8.0 Species % C % C % C % C % C % C Cotton 90 100 100 30 80 70 Soybean 40 90 80 20 50 40 Field Corn 60 100 60 10 60 20 Rice 60 50 90 - - - heat 70 80 100 0 40 20 Field Bindweed 70 100 100 40 70 40 Morningglory 90 100 90 0 80 50 Velvetleaf 100 100 100 20 100 90 Barnyardgrass 60 100 100 30 70 40 Green Foxtail 50 100 100 20 70 40 Johnsongrass 60 90 100 20 80 50 Yellow Nutsedge 20 40 70 - 100 - Compound No. 179 180 181 182 183 184 Rate (kg/ha) 4.0 8.0 8.0 2.0 1.0 1.0 Species % C % C % C % C % C % C Cotton 100 40 30 80 90 100 Soybean 40 30 30 30 30 50 Field Corn 30 20 20 20 20 30 Rice 40 - - 60 90 80 Wheat 20 0 10 50 50 50 Field Bindweed 100 50 0 90 100 100 Morningglory 100 40 30 80 90 100 Velvetleaf 100 50 60 100 100 100 Barnyardgrass 100 30 90 100 80 90 Green Foxtail 100 30 30 90 90 90 Johnsongrass 50 30 0 50 50 40 Yellow Nutsedge 20 - - 60 30 50 Table 4 Postemergence Herbicidal Activity Compound No. 185 186 187 188 189 190 Rate (kg ha) 1.0 8.0 0.5 1.0 1.0 0.125 Species % C % C % C % C % C % C Cotton 50 0 90 100 10 100 Soybean 30 10 20. 70 10 60 Field Corn 20 10 0 10 0 70 Rice 40 - 0 90 0 100 Wheat 20 10 0 100 0 80 Field Bindweed 70 0 50 100 0 100 Morningglory 60 0 20 90 0 30 Velvetleaf 100 0 100 100 0 100 Barnyardgrass 50 0 0 100 10 90 Green Foxtail 60 0 10 100 0 100 Johnsongrass 60 0 60 80 0 70 Yellow Nutsedge 20 - 0 90 0 40 Compound No. 191 192 193 194 195 196 Rate (kg ha) 1.0 1.0 1.0 1.0 1.0 8.0 Species % C % C % C % C % C % C Cotton 80 40 90 60 100 60 Soybean 70 30 90 80 60 40 Field Corn 70 10 100 20 50 10 Rice 70 0 100 0 60 - Wheat 80 0 30 10 10 30 Field Bindweed 90 80 100 100 100 100 Morningglory 90 10 100 30 100 30 Velvetleaf 100 90 100 100 100 100 Barnyardgrass 100 20 100 60 100 30 Green Foxtail 100 100 100 80 100 30 Johnsongrass 90 70 100 20 70 20 Yellcw Nutsedge 10 0 70 0 20 - Table 4 Postemergence Herbicidal Activity Cotton 80 90 90 60 90 90 Soybean 30 20 40 60 90 40 Field Corn 30 10 20 40 20 30 Rice - - 10 10 20 10 Wheat 50 40 50 0 40 10 Field Bindweed 100 100 90 20 60 10 Morningglory 80 60 90 20 10 60 Velvetleaf 100 100 100 10 100 100 Barnyardgrass 80 40 0 10 10 0 Green Foxtail 100 50 100 70 90 50 Johnsongrass 60 30 10 0 30 0 Yellow Nutsedge - - 0 0 10 0 Compound No. 203 204 205 206 207 208 Rate (kg/ha) 0.5 0.5 0.5 0.25 4.0 0.5 Species % C % C % C % C % C % C Cotton 90 90 100 100 90 100 Soybean 80 80 50 70 90 60 Field Corn 70 80 40 40 30 30 Rice 30 40 40 70 20 50 Wheat 50 100 90 60 30 70 Field Bindweed 100 90 90 100 40 90 Morningglory 90 100 90 100 30 100 Velvetleaf 100 100 100 100 100 100 Barnyardgrass - - - - - 60 Green Foxtail 80 100 100 100 40 90 Johnsongrass 40 70 50 90 20 70 Yellcw Nutsedge 40 50 60 40 30 30 ^ XO f OMPI K WIPO V N AT lO Table 4 Postemergence Herbicidal Activity Ccttpound No. 209 210 212 213 214 215 Rate (kg ha) 1.0 8.0 8.0 8.0 8.0 8.0 Species % C % C % C % C % C % C Cotton 100 0 0 10 0 100 Soybean 40 0 0 10 0 100 Field Corn 20 0 0 10 0 100 Rice 100 - - - - 100 heat 90 0 0 0 0 100 Field Bindweed 100 0 0 0 0 100 Morningglory 100 0 0 80 0 100 Velvetleaf 100 0 0 0 0 100 Barnyardgrass 100 0 0 0 0 100 Green Foxtail 100 0 0 0 0 100 Johnsongrass 70 0 0 0 0 100 Yellow Nutsedge 70 - - - - 80 Compound No. 216 217 218 219 220 221 Rate (kg ha) 2.0 8.0 0.5 0.5 2.0 1.0 Species % C % C % C % C % C % C Cotton 100 80 100 90 100 100 Soybean 90 40 60 60 90 90 Field Corn 90 10 70 60 50 90 Rice . 90 - 90 50 100 95 Wheat 100 20 60 70 60 90 Field Bindweed 100 80 100 100 100 100 Morningglory 100 70 100 100 100 100 Velvetleaf 100 100 100 100 100 100 Barnyardgrass 100 40 90 100 60 100 Green Foxtail 100 20 100 60 50 95 Johnsongrass 100 10 90 90 60 90 Yellow Nutsedge 80 - 90 40 40 40 Table 4 Postemergence Herbicidal Activity Compound No. 222 223 224 225 Rate (kg ha) 1.0 1.0 0.5 0.5 Species % C % C % C % C Cotton 100 95 100 100 Soybean 90 50 95 100 Field Corn 80 50 100 100 Rice 60 40 95 90 Wheat 70 . 30 100 95 Field Bindweed 90 70 100 100 Morningglory 90 95 100 100 Velvetleaf 100 80 100 100 Barnyardgrass 100 30 100 100 Green Foxtail 100 10 100 100 Johnsongrass 70 20 100 100 Yellow Nutsedge 30 10 95 40

Claims: Claims: 1. A compound of the formula characterized in that W is oxygen or sulfur; R is alkyl of 1 to 6 carbon atoms, fluoroalkyl of 1 • j^0 to 5 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, alkylthioalkyl of 2 to 6 carbon atoms, cyanoalkyl of 1 to 5 alkyl carbon atoms, haloalkoxyalkyl of 2 to 6 carbon atoms, trifluoromethylthio, alkenyl of 2 to 5 carbon atoms, or haloalkenyl of 2 to 5 carbon atoms? 5 one of X 1 and X2 is fluorine, chlorine, or bromine and the other is fluorine, chlorine, bromine, alkyl of 1 to 6 carbon atoms, or haloalkyl of 1 to 5 carbon atoms; or X 1 is fluorine, chlorine, or bromine and X2 is selected from the substituents above and nitro; and 0 Z is selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, alkyl of 1 to 6 carbon atoms, alkyl of 1 to 5 carbon atoms substituted with fluorine, chlorine, bromine, or alkoxy of 1 to 4 carbons, and alkynyl of 3 to 5 carbon atoms. 5 2. The compound of claim 1 characterized in that W is oxygen, R is n-propyl or 3-fluoropropyl, X is 2 fluorine or chlorine, and X is chlorine. 3. A compound of the formula 5 characterized in that W is oxygen or sulfur; R is alkyl of 1 to 6 carbon atoms, fluoroalkyl of 1 to 5 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, alkylthioalkyl of 2 to 6 carbon atoms, cyanoalkyl of 1 to 5 alkyl carbon atoms, haloalkoxyalkyl of 2 to 6 carbon atoms, trifluoromethylthio, alkenyl of 2 to 5 carbon atoms, or haloalkenyl of 2 to 5 carbon atoms; one of X 1 and X2 is fluorine, chlorine, or bromine and the other is fluorine, chlorine, bromine, alkyl of 1 to 6 carbon atoms, or haloalkyl of 1 to 5 carbon atoms; or X 1 is fluorine, chlorine, or bromine and X2 is selected from the substituents above and nitro; and °) , r; of 1 to 5 carbon atoms, hydroxyalkyl of 1 to 5 carbon atoms, cyanoalkyl of 1 to 5 alkyl carbon atoms, alkoxy¬ alkyl of 2 to 6 carbon atoms, alkylthioalkyl, alkyl- sulfinylalkyl, or alkylsulfonylalkyl (each of 2 to 6 carbon atoms), alkanoyl of 2 to 5 carbon atoms, alkenyl of 2 to 5 carbon atoms, haloalkenyl of 2 to 5 carbon atoms, alkenyloxyalkyl of 3 to 6 carbon atoms, alkynyl of 2 to 5 carbon atoms, haloalkynyl of 2 to 5 carbon atoms, alkoxycarbonyl of 1 to 4 alkyl carbon atoms, or a three- to eight-membered ring heterocyclic group of one or two, same or different, ring heteroatoms selected • from oxygen and sulfur or an alkyl radical of 1 to 4 carbon atoms substituted with said heterocyclic group; 2 R is alkyl of 1 to 8 carbon atoms, haloalkyl, cyanoalkyl, or arylalkyl wherein each alkyl is of 1 to " 5 carbon atoms, cyclic alkyl of 3 to 8 carbon atoms, alkenyl, haloalkenyl, or arylalkenyl wherein each alkenyl is of 2 to 5 carbon atoms, alkynyl, haloalkynyl, or arylalkynyl wherein each alkynyl is of 2 to 5 carbon atoms, phenyl, or a group of the formula -(CH„__)mNR 3 R 4 or (CH_;)n-Y-R 5 wherein m is 0 to 5 and n is 1 to 5; R 3 is hydrogen or alkyl of 1 to 5 carbon atoms; R 4 is alkyl of 1 to 5 carbon atoms or a group alkyl of 1 to 5 carbon atoms, alkenyl or alkynyl of 2 to 5 carbon atoms, or a radical -CH(R 18)CO,R19: R 18 and R19 are independently hydrogen or alkyl of 1 to 4 carbon atoms; and Y is oxygen or S(O) in which r is 0 to 2; 7 * ■ R is an alkylene or fluoroalkylene radical of 1 to 3 carbon atoms; R is hydrogen, alkyl or substituted alkyl of 1 to 8 carbon atoms, alkenyl or alkynyl of 2 to 5 car¬ bon atoms, phenyl, 3-tetrahydrofuranyl, 2-oxo-3-tetra- hydro uranyl, 3-tetrahydrothienyl or the oxide or dioxide thereof, 3-pyridyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, tetrahydrofurfuryl, furfuryl, thenyl, or benzyl; one of R 9 and R10 is alkyl and the other is alkyl or alkylthio, each alkyl (independently) being of 1 to 4 carbon atoms; R 11 is oxygen or N-OR20 in which R20 is hydro- gen or alkyl of 1 to 4 carbon atoms; and one of R 12 and R13 is hydrogen, alkyl of 1 to 4 carbon atoms, or alkenyl of 3 to 5 carbon atoms and the • other is hydrogen, alkyl of 1 to 4 carbon atoms, cyanoalkyl of 1 to 4 alkyl carbon atoms, alkoxyalkyl of 2 to 4 carbon atoms, alkenyl of 3 to 5 carbon atoms, alkynyl of 3 to 5 carbon atoms, alkylsulfonyl of 1 to-4 carbon atoms, arylsulfonyl in which aryl is unsubsti¬ tuted phenyl or phenyl substituted with halogen or alkyl of 1 to 4 carbon atoms, haloalkylsulfonyl of 1 to 4 carbon atoms, alkylaminosulfonyl or dialkylaminosulfonyl in which each alkyl independently is of 1 to 4 carbon OMPI / _ ipo ^ ato s, or CH(H or CH,)C0,alkyl in which alkyl is of 1 to 4 carbon atoms, or N(R 1 )(R13) is a pyrrolidino, piperidino, or morpholino ring. 4. The compound of claim 3 characterized in that W is oxygen, R is n-propyl or 3-fluoropropyl, X is 2 fluorine or chlorine, and X is chlorine. 5. A compound of the formula characterized in that W is oxygen or sulfur; R is alkyl of 1 to 6 carbon atoms, fluoroalkyl of 1 to 5 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, alkylthioalkyl of 2 to 6 carbon atoms, cyanoalkyl of 1 to 5 alkyl carbon atoms, haloalkoxyalkyl of 2 to 6 carbon atoms, trifluoromethylthio, alkenyl of 2 to 5 carbon atoms, or haloalkenyl of 2 to 5 carbon atoms; one of X 1 and X2 is fluorine, chlorine, or bromine and the other is fluorine, chlorine, bromine, alkyl of 1 to 6 carbon atoms, or haloalkyl of 1 to 5 carbon atoms; or 1 is fluorine, chlorine, or bromine and X2 is selected from the substituents above and nitro; and z is -N(R 14 )(R 15 ), -SO,R 16 , or -CO-R 17 ; R 14 and R15 are independently selected from hydro¬ gen, alkyl of 1 to 4 carbon atoms, alkenyl or alkynyl of 3 to 5 carbon atoms, cyanoalkyl of 1 to 4 alkyl carbon atoms, acetyl, alkoxycarbonyl of 1 to 4 alkyl carbon atoms, alkoxyalkyl of 2 to 4 carbon atoms, aminocar- bonyl, alkylaminocarbonyl or dialkylaminocarbonyl in which each alkyl is of 1 to 4 carbon atoms, alkylsul¬ fonyl of 1 to 4 carbon atoms, haloalkylsulfonyl of 1 to 4 carbon atoms, arylsulfonyl in which aryl is unsubstituted phenyl or phenyl substituted with halogen or alkyl of 1 to 4 carbon atoms, or CH(H or CH 3 )C0 2 - alkyl in which alkyl is of 1 to 4 carbon atoms, or N(R 14 )(R 15 ) is a group N=C(R 9 ) (R 10 ) in which one of R 9 and R is alkyl and the other is hydrogen, alkyl, or alkylthio, each alkyl (independently) being of 1 to 4 carbon atoms, or N(R ) (R ) is a tetrahydrophthalimido or 2-oxopyrrolidino group; R is hydroxy, amino, alkylamino or dialkyl- amino in which each alkyl is of 1 to 4 carbon atoms, or arylamino in which aryl is unsubstituted phenyl or phenyl substituted with halogen or alkyl of 1 to 4 carbon atoms; and R 17 is hydroxy, alkoxy or alkylthio of 1 to 4 carbon atoms, amino, alkylamino or dialkylamino in which each alkyl is of 1 to 4 carbon atoms, or arylamino in which aryl is unsubstituted phenyl or phenyl substituted with halogen or alkyl of 1 to 4 carbon atoms. 6. The compound of claim 5 characterized in that W is oxygen, R is n-propyl, or 3-fluoropropyl, X is fluorine 2 or chlorine, and X is chlorine. 7. A compound of the formula characterized in that W is oxygen or sulfur; R is alkyl of 1 to 6 carbon atoms, fluoroalkyl of 1 to 5 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, alkylthioalkyl of 2 to 6 carbon atoms, cyanoalkyl of 1 to 5 alkyl carbon atoms, haloalkoxyalkyl of 2 to 6 carbon atoms, trifluoromethylthio, alkenyl of 2 to 5 carbon atoms, haloalkenyl of 2 to 5 carbon atoms, 2-oxopropyl, or 3-oxopropyl; one of X 1 and X2 is fluorine, chlorine, or bro¬ mine and the other is fluorine, chlorine, bromine, alkyl OMPI of 1 to 6 carbon atoms, or haloalkyl of 1 to 5 carbon atoms; or X is fluorine, chlorine, or bromine and X is selected from the substituents above and nitro; and Z is hydroxy, mercapto, or benzyloxy. 8. The compound of claim 7 characterized in that W is oxygen, R is n-propyl or 3-fluoropropyl, X is fluorine or chlorine, and X 2 is chlorine. 9. A compound of the formula characterized in that 1 2 one of X and X is fluorine, chlorine, or bromine and the other is fluorine, chlorine, bromine, alkyl of 1 to 6 carbon atoms, or haloalkyl of 1 to 5 carbon atoms; or X 1 is fluorine, chlorine, or bromine and X2 is selected from the substituents above and nitro; and Z is hydrogen, fluorine, chlorine, bromine, cyano, nitro, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 5 carbon atoms, alkynyl of 3 to 5 carbon atoms, or QR in which Q is sulfur or oxygen and R is alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 5 carbon atoms, cyanoalkyl of 1 to 5 alkyl carbon atoms, alkoxyalkyl of * 2 to 6 carbon atoms, alkylthioalkyl, alkylsulfinylalkyl, or alkylsulfonylalkyl (each of 2 to 6 carbon atoms), alkenyl of 2 to 5 carbon atoms, haloalkenyl of 2 to 5, carbon atoms, alkenyloxyalkyl of 3 to 6 carbon atoms, alkynyl of 2 to 5 carbon atoms or haloalkynyl of 2 to 5 carbon atoms. 10. The compound of dim 9 characterized in that W is oxygen, X 1' is fluorine or chlorine, X2 is chlorine, and Z is -OR in which R is benzyl or alkyl of 1 to 4 carbon atoms. 11. An herbicidal composition characterized in that it contains an herbicidally effective amount of a compound of any one of claims 1-6 in admixture with a suitable carrier. 12. A method for controlling undesired plant growth characterized in applying to the locus where control is desired an herbicidally effective amount of the composition of claim 11. 13. The method of claim 12 characterized in that the locus where . control is desired is planted or to be planted with soybeans, corn, or cotton. OMPI *_> IP ° & 14. A process for producing a compound of the formula in which W is oxygen or sulfur; R is alkyl of 1 to 6 carbon atoms, fluoroalkyl of 1 to 5 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, alkylthioalkyl of 2 to 6 carbon atoms, cyanoalkyl of 1 to 5 alkyl carbon atoms, haloalkoxyalkyl of 2 to 6 carbon atoms, trifluoromethylthio, alkenyl of 2 to 5 carbon atoms, or haloalkenyl of 2 to 5 carbon atoms; 1 one of X and X is fluorine, chlorine, or bromine and the other is fluorine, chlorine, bromine, alkyl of 1 to 6 carbon atoms, or haloalkyl of 1 to 5 carbon atoms; or X 1 is fluorine, chlorine, or bromine and X2 s selected from the substituents above and nitro; and Z is selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, alkyl of 1 to 6 carbon atoms, alkyl of 1 to 5 carbon atoms substituted with fluorine, chlorine, bromine, or alkoxy of 1 to 4 carbons, and alkynyl of 3 to 5 carbon atoms; characterized by reacting a compound of the formula OMPI " v Λ* • V W .¥I_P_ ■ O*- ■ . v t . , - 1 2 with R-X in the presence of a base, , X . X . Z, and R being as defined above and X being a leaving group. 15. The process of claim 14 characterized in that W is oxygen, R is n-propyl or 3-fluoropropyl, X is fluo- rine or chlorine, and X 2 is chlorine. 16. process for producing a compound of the formula in which W is oxygen or sulfur; R is alkyl of 1 to 6 carbon atoms, fluoroalkyl of 1 to 5 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, alkylthioalkyl of 2 to 6 carbon atoms, cyanoalkyl of 1 to 5 alkyl carbon atoms, haloalkoxyalkyl of 2 to 6 carbon " atoms, trifluoromethylthio, alkenyl of 2 to 5 carbon atoms, or haloalkenyl of 2 to 5 carbon atoms; 1 2 one of X and X is fluorine, chlorine, or bromine and the other is fluorine, chlorine, bromine, alkyl of 1 to 6 carbon atoms, or haloalkyl of 1 to 5 carbon atoms; or X 1 is fluorine, chlorine, or bromine and X2 is selected from the substituents above and nitro; and R 10 ) , fur; ' l of 1 to 5 carbon atoms, hydroxyalkyl of 1 to 5 carbon atoms, cyanoalkyl of 1 to 5 alkyl carbon atoms, alkoxy- alkyl of 2 to 6 carbon atoms, alkylthioalkyl, alkyl¬ sulfonylalkyl, or alkylsulfonylalkyl (each of 2 to 6 carbon atoms), alkanoyl of 2 to 5 carbon atoms, alkenyl of 2 to 5 carbon atoms, haloalkenyl of 2 to 5 carbon atoms, alkenyloxyalkyl of 3 to 6 carbon atoms, alkynyl of 2 to 5 carbon atoms, haloalkynyl of 2 to 5 carbon atoms, alkoxycarbonyl of 1 to 4 alkyl carbon atoms, or a OMPI - 1J5- three- to eight-membered ring heterocyclic group of one or two, same or different, ring heteroatoms selected from oxygen and sulfur or an alkyl radical of 1 to 4 carbon atoms substituted with said heterocyclic group; R 2 is alkyl of 1 to 8 carbon atoms, haloalkyl, cyanoalkyl, or arylalkyl wherein each alkyl is of 1 to 5 carbon atoms, cyclic alkyl of 3 to 8 carbon atoms, alkenyl, haloalkenyl, or arylalkenyl wherein each alkenyl is of 2 to 5 carbon atoms, alkynyl, haloalkynyl, or arylalkynyl wherein each alkynyl is of 2 to 5 carbon atoms, phenyl, or a group of the formula -(CH 2 ) m NR 3 R 4 or (CH 2 ) n -Y-R 5 wherein m is 0 to 5 and n is 1 to 5; R is hydrogen or alkyl of 1 to 5 carbon atoms; 4 R is alkyl of 1 to 5 carbon atoms or a group alkyl of 1 to 5 carbon atoms, alkenyl or alkynyl of 2 to 5 carbon atoms, or a radical -CH(R 18)C0 9 R1 R 18 and R1 are independently hydrogen or alkyl of 1 to 4 carbon atoms; and Y is oxygen or S(0) in which r is 0 to 2; R 7 is an alkylene or fluoroalkylene radical of 1 to 3 carbon atoms; g R i s hydrogen , alkyl or substituted alkyl of 1 to 8 carbon atoms , alkenyl or alkynyl of 2 to 5 car¬ bon atoms , phenyl , 3-tetrahydrof uranyl , ' 2-oxo-3-tetra- hydrof uranyl , 3-tetrahydrothienyl or the oxide or dioxide thereof , 3-pyridyl , cyclopropyl , cyclopentyl , cyclohexyl , cyclopropylmethyl , tetrahydrofurf uryl , furfuryl , thenyl , or benzyl ; one of R 9 and R 1 0 i s alkyl and the othe r i s alkyl or alkylthio , each alkyl ( independently) being of 1 to 4 carbon atoms; R is oxygen or N-OR in which R is hydro- gen or alkyl of 1 to 4 carbon atoms; and 1 13 one of R and R i s hydrogen , alkyl of 1 to 4 Λ2 - carbon atoms, or alkenyl of 3 to 5 carbon atoms and the other is hydrogen, alkyl of 1 to 4 carbon atoms, cyanoalkyl of 1 to 4 alkyl carbon atoms, alkoxyalkyl of 2 to 4 carbon atoms, alkenyl of 3 to 5 carbon atoms, alkynyl of 3 to 5 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, arylsulfonyl in which aryl is unsubsti¬ tuted phenyl or phenyl substituted with halogen or alkyl of 1 to 4 carbon atoms, haloalkylsulfonyl of 1 to 4 carbon atoms, alkylaminosulfonyl or dialkylaminosulfonyl in which each alkyl independently is of 1 to 4 carbon atoms, or CH(H or CH,)CO,alkyl in which alkyl is of 1 to 4 carbon atoms, or N(R 12)-(R13) is a pyrrolidino, piperidino, or morpholino ring; characterized by reacting the appropriate compound of the formula a leaving group. 17. The process of claim 16 characterized in that W is oxygen, R is n-propyl or 3-fluoropropyl, is fluo- πne or chlorine, and X 2 is chlorine. 18. A process for producing a compound of the formula in which W is oxygen or sulfur; R is alkyl of 1 to 6 carbon atoms, fluoroalkyl of 1 to 5 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, alkylthioalkyl of 2 to 6 carbon atoms, cyanoalkyl of 1 to 5 alkyl carbon atoms, haloalkoxyalkyl of 2 to 6 carbon atoms, trifluoromethylthio, alkenyl of 2 to 5 carbon atoms, or haloalkenyl of 2 to 5 carbon atoms; one of and X is fluorine, chlorine, or bromine and the other is fluorine, chlorine, bromine, alkyl of 1 to 6 carbon atoms, oc haloalkyl of 1 to 5 carbon atoms; or 1 is fluorine, chlorine, or bromine and 2 is selected from the substituents above and nitro; and Z is -QR 7 -CO-SR 8 , -QR 7 CO,N=C(R 9 ) (R 10 ) , or -QR 7'CON(R1 ,z )(R1 , 3 J ); Q is oxygen or sulfur; 7 R • is an alkylene or fluoroalkylene radical o£ 1 to 3 carbon atoms; R is hydrogen, alkyl or substituted alkyl of 1 to 8 carbon atoms, alkenyl or alkynyl of 2 to 5 car- bon atoms, phenyl, 3-tetrahydrofuranyl, 2-oxo-3-tetra- hydro uranyl , 3-tetrahydrothienyl or the oxide or dioxide thereof, 3-pyridyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyl ethyl, tetrahydrof rfuryl, furfuryl, thenyl, or benzyl; one of R 9 and R10 is alkyl and the other is alkyl or alkylthio, each alkyl (independently) being of 1 to 4 carbon atoms; and one of R 12 and R13 is hydrogen, alkyl of 1 to 4 carbon atoms, or alkenyl of 3 to 5 carbon atoms and the other is hydrogen, alkyl of 1 to 4 carbon atoms, cyanoalkyl of 1 to 4 alkyl carbon atoms, alkoxyalkyl of 2 to 4 carbon atoms, alkenyl of 3 to 5 carbon atoms, alkynyl of 3 to 5 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, arylsulfonyl in which aryl is unsubsti- tuted phenyl or phenyl substituted with halogen or alkyl of 1 to 4 carbon atoms, haloalkylsulfonyl of 1 to 4 - 2- carbon atoms, alkylaminosulfonyl or dialkylaminosulfonyl in which each alkyl independently is of 1 to 4 carbon atoms, or CH(H or CH 3 )C0 2 alkyl in which alkyl is of 1 to 4 carbon atoms, or N(R 12 )(R 13 ) is a pyrrolidino, piperidino, or morpholino ring; characterized by reacting the compound of the formula with R 8 SH, HO-N=C(R 9 )(R 10 ), or ϊψ(R 12 )(R 13) 7 « 9 in the presence of a base, W, X , X , R, Q, R , R , R , R , R , and R being as defined above and X being a leaving group. 19. The process of claim 18 characterized in that X is a chlorine, bromine, or iodine atom. 20. A process for producing a compound of the formula in which W is oxygen or sulfur; R is alkyl of 1 to 6 carbon atoms, fluoroalkyl of 1 to 5 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, alkylthioalkyl of 2 to 6 carbon atoms, cyanoalkyl of 1 to 5 alkyl carbon atoms, haloalkoxyalkyl of 2 to 6 carbon atoms, trifluoromethylthio, alkenyl of 2 to 5 carbon atoms,, or haloalkenyl of 2 to 5 carbon atoms; one of X 1 and X2 is fluorine, chlorine, or bromine and the other is fluorine, chlorine, bromine, alkyl of 1 to 6 carbon atoms, or haloalkyl of 1 to 5 carbon 1 2 atoms; or X is fluorine, chlorine, or bromine and X is selected from the substituents above and nitro; and Z is -N(R 14 )(R 15 ), -S0 2 R 16 , or -CO-R 17 ; R 14 and R 15 are independently selected from hydro¬ gen, alkyl of 1 to 4 carbon atoms, alkenyl or alkynyl of 3 to 5 carbon atoms, cyanoalkyl of 1 to 4 alkyl carbon atoms, acetyl, alkoxycarbonyl of 1 to 4 alkyl carbon atoms, alkoxyalkyl of 2 to 4 carbon atoms, aminocar- bonyl, alkylaminocarbonyl or dialkylaminocarbonyl in which each alkyl is of 1 to 4 carbon atoms, alkylsul¬ fonyl of 1 to 4 carbon atoms, haloalkylsulfonyl of 1 to 4 carbon atoms, arylsulfonyl in which aryl is unsub¬ stituted phenyl or phenyl substituted with halogen or alkyl of 1 to 4 carbon atoms, or CH(H or CH 3 )CO 2 ~ alkyl in which alkyl is of 1 to 4 carbon atoms, or N(R 1 )(R 15 ) is a group N=C( 9 ) (R 1 °) in which one Q in of and R is alkyl and the other is hydrogen, alkyl, or alkylthio, each alkyl (independently) being of 1 to 4' carbon atoms, or N(R 14)(R15) is a tetrahydro- phthali ido or 2-oxopyrrolidino group; R 16 is hydroxy, amino, alkylamino or dialkyl- amino in which each alkyl is of 1 to 4 carbon atoms, or arylamino in which aryl is unsubstituted phenyl or phenyl substituted with halogen or alkyl of 1 to 4 carbon atoms; and R 17 is hydroxy, alkoxy or alkylthio of 1 to 4 carbon atoms, amino, alkylamino or dialkylamino in which each alkyl is of 1 to 4 carbon atoms, or arylamino in which aryl is unsubstituted phenyl or phenyl substituted with halogen or alkyl of 1 to 4 carbon atoms; characterized by (a) reducing a compound of the formula above in which z is -NO 2 to give the corresponding compound in which Z is -NH 2 and converting the compound in which Z is -NH 2 to the compound in which Z is -N(R 14 )(R 15 ), or (b) treating a compound of the formula above in which z is -S0 2 X in the presence of a base with R 16 -H to - 150 - give the corresponding compound in which Z is -S0 2 , or (c) treating a compound of the formula above in which Z is -CO-X in the presence of a base with R 17-H to give the corresponding compound in which Z is -CO-R 17, X being a leaving group. 21. i jhe process of claim 20 characterized in that X is a chlorine, bromine, or iodine atom.

Inventors: THEODORIDIS GEORGE, THEODORIDIS, GEORGE
Applicants: FMC CORP, FMC CORPORATION
Application year: 1984
Main classification: C07D257
IPC codes: A01N43, C07C205, C07D257, C07D403, C07D405, C07D409