CERTAIN 2-(2'NITROBENZOYL)-1,3-CYCLOHEXANEDIONES

Abstract: Compounds of the formula wherein R¹ is hydrogen or C₁-C₄ alkyl; R² is hydrogen, C₁-C₄ alkyl or R a -O-- wherein R a is C₁-C₄ alkyl; R¹ and R² together are alkylene having 3 to 6 carbon atoms; R³ is hydrogen or C₁-C₄ alkyl; R⁴ is hydrogen or C₁-C₄ alkyl, R⁵ is hydrogen or C₁-C₄ alkyl; R⁶ is hydrogen or C₁-C₄ alkyl; and R⁷ and R⁸ independently are (1) hydrogen; (2) halogen; (3) C₁-C₄ alkyl; (4) C₁-C₄ alkoxy; (5) OCF₃; (6) cyano; (7) nitro; (8) C₁-C₄ haloalkyl; (9) R b SO n - wherein n is the integer 0, 1 or 2; and R b is (a) C₁-C₄ alkyl; (b) C₁-C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) -NR c R d wherein R c and R d independently are hydrogen or C₁-C₄ alkyl; (11) R e C(O)-wherein R e is C₁-C₄ alkyl or C₁-C₄ alkoxy; or (12) SO₂NR c R d wherein R c and R d are as defined, with the proviso that R⁷ is not attached to the 6-position, are effective as herbicides.

Description: CERTAIN 2-(2'-NITROBENZOYL)-1,3-CYCLOHEANEDIONES Background of the Invention Compounds having the structural formula EMI1.1 wherein X can be an alkyl, n can be 0, 1, or 2, and R1 can be phenyl or substituted phenyl are described in Japanese Patent Application 84632-1974 as being intermediates for the preparation of herbicidal compounds of the formula EMI1.2 wherein R1, X, and n are as defined above and R2 is alkyl, alkenyl, or alkyl Specifically taught herbicidal compounds of this latter group are those where n is 2, X is 5,5-dimethyl, R2 is allyl and R1 is phenyl, 4-chlorophenyl or 4-methoxyphenyl. me precursor intermediates for these three specifically taught canpounds have no or almost no herbicidal activity. European Patent Application No. 83 102 599.4 was published October 5, 1983 ard relates to certain novel 2-(2-substituted benzoyl) cyclohexane-l, 3-diones as herbicides. The compounds have the following structural formula EMI1.3 wherein R and R1 are hydrogen or C1-C4 alkyl; R2 is chlorine, bromine, or iodine; R3 is hydrogen or halogen; and R4 is hydrogen, chlorine, branine, iodine, C1-C4 alkyl, t-C4 alkoxy, nitro or trifluoranethyl. Description of the Invention This invention relates to 2-(2-nitrobenzoyl)-1,3-cyclohexane- diones and their use as herbicides. The canpounds have a nitro substitution in the 2-position of the phenyl moiety of their compounds. The nitro substitution imparts exceptional herbicidal activity to the compounds of this invention. One embodiment of this invention is an herbicidal composition comprising an herbicidally active 2-(2-nitrobenzoyl)-1,3-cyclohexanedione and an inert carrier therefor. The 4-, 5- and 6-positions of the 1,3-cyclohexanedione moiety can be substituted, preferably with the groups hereinafter recited. More preferably, the 1,3-cyclohexanedione moiety has no substitution or the 4- or 6-positions are substituted with one or two methyl groups. The 3-, 4- and 5-positions of the benyl moiety can be substituted, preferably with the groups hereinafter recited. Also embodied within the scope of this invention are navel compounds having the following structural formula EMI2.1 wherein R1 is hydrogen or C14 alkyl, preferably C1-C2 alkyl, more preferably methyl, most preferably R1 is hydrogen or methyl; R2 is hydrogen; C1-C4 alkyl, preferably C1-C2 alkyl, more preferably methyl or EMI2.2 wherein Ra is C1-C4 alkyl, most preferably R2 is hydrogen or methyl; or R1 and R2 together are alkylene having 3 to 6 carbon atoms; R3 is hydrogen or C1-C4 alkyl, preferably C1-C2 alkyl, more preferably methyl; most preferably R3 is hydrogen or methyl; R4 is hydrogen or C1-C4 alkyl, preferably Cl-C2 alkyl, more preferably methyl; most preferably R4 is hydrogen or methyl; R5 is hydrogen or C1-C4 alkyl, preferably C1-C2 alkyl, more preferably methyl; most preferably R5 is hydrogen or methyl; R6 is hydrogen or C1-C4 alkyl, preferably C1-C2 alkyl, more preferably methyl, most preferably R6 is hydrogen; R7 and R8 independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C1-C4 alkyl, preferably methyl; (4) C1-C4 alkoxy, preferably methoxy; (5) OCF3; (6) cyano (7) nitro; (8) C1-C4 haloalkyl, more preferably trifluoromethyl; (9) RbSOn- wherein n is the integer 0, 1 or 2, preferably 2; and Rb is (a) C1-C4 alkyl, preferably methyl; (b) C1-C4 alkyl substituted with halogen or cyano, preferably chloranethyl, trifluoromethyl or cyano methyl; (c) phenyl; or (d) benzyl; (10) -NRcRd wherein Rc and Rd independently are hydrogen or C1-C4 alkyl; (11) ReC(O)- wherein Re is C1-C4 alkyl or C1-C4 alkoxy; or (12) -SO2NRcRd wherein Rc and Rd are as defined, with the proviso that R7 is not attached to the 6-position. Preferably, R7 is in the 3-position. MDst preferably R7 is hydrogen or C1-C4 alkoxy and R8 is hydrogen, chlorine, branine, fluorine, CF3, or RbSO2 wherein Rb is C1-C4 alkyl, preferably methyl. The term "C1-C4 alkyl includes methyl, ethyl. n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. The terms "C1-C4 alkoxy" includes methoxy, ethoxy, n-propoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "haloalkyl" includes the eight alkyl groups with one or more hydrogens replaced by chlorine, bromine, iodine or fluorine. Salts of the above-described compounds (as defined hereinafter) are also the subject of the instant invention. The compounds of this invention can have the following four structural formulae because of tautanerisn: EMI4.1 wherein R1, R2, R3, R4, R5, R6, R7 and R8 are as defined above. The circled proton On each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: EMI4.2 wherein R1, R2, R3, R4, R5, R6, R7 and R8 are as defined above. Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodiun, and potassium organic cations such as substituted ammonium, sulfoniun or phosphonium Wherein the substitutent is an aliphatic or aranatic group. The compounds of this invention and their salts are active herbicides of a general type. Ihat is, they are herbicidally effective against a wide range of plant species. The method of controlling undesirable vegetation of the present invention comprises applying an herbicidally effective amount of the above-described compounds to the area where control is desired. The compounds of the present invention can be prepared by the following step general method. The e process proceeds via the production of an enol ester intermediate as shown in reaction (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using oonventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction mediun after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reacton (1). EMI5.1 <tb> <SEP> R2 <SEP> R1 <tb> <SEP> O1R7 <SEP> Moderate <tb> 1) <SEP> t <SEP> + <SEP> X-C <SEP> x-c8 <SEP> Base <tb> <SEP> R4 <SEP> 0 <tb> <SEP> R5 <SEP> R6 <tb> <SEP> R4 <SEP> R3 <SEP> R2 <SEP> R1 <SEP> N32 <tb> <SEP> R5 <SEP> > <SEP> c?I/R7B <tb> <SEP> R6 <tb> wherein R1 through R8 and moderate base are as defined and X is halogen, preferably chlorine, C1-C4 alkyl-C(O)-O-, C1-C4 alkoxy-C(O)-O- or EMI5.2 wherein R7 and R8 in this portion of the molecule are identical with those in the reactant shown above and the moderate base is as defined, preferably tri-C1-C6 alkylanine, pyridine, alkali metal carbonate or alkali metal psos- phate. Generally, in step (1) mole amounts of the dione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. two two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate or dimethylformanide. The base or benzoyl reactant preferably are added to the reaction mixture with candling. The e mixture is stirred at 0 C-50 C until the reaction is substantially complete. EMI6.1 <tb> <SEP> R4 <SEP> R3 <SEP> R2 <SEP> R1 <SEP> No2 <SEP> R2 <SEP> R1 <tb> <SEP> R5 <SEP> R7 <SEP> R3 <tb> 2) <SEP> W <SEP> --C <SEP> ss <SEP> 8 <SEP> * <SEP> ffi <SEP> < <SEP> g <SEP> 8 <tb> <SEP> R6 <SEP> o <SEP> - <SEP> Moderate <SEP> Ease <tb> <SEP> R5 <SEP> R6 <tb> * = Cyanide source. wherein the moderate base and R1 through R8 are as defined above. Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably around 0.1 mole of the cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 50-C, preferably about 20 C to about 40"C, and the desired product is recovered by conventional techniques. The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion. The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base. Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having fran 1-4 carbon atans in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C25 aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc., cyanohy- drins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpensive. Among cyanohydrins the preferred cyanide source is acetone cyanohyd rin. The cyanide source is used in an amount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction at about 400C on a snall scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred. The process is conducted with a molar excess, with respect to the enol ester, of a moderate base. By the term "moderate base" is meant a substance which acts as a base yet ose se strength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effectively). Mbderate bases suitable for use in this embodiment include both organic bases such as tertiary amines and inorganic bases such as alkali metal carbonates and phosphates. Suitable tertiary amines include trialkylanines such as triethylamine, trialkanolanines such as triethanolanine, and pyridine. Suitable inorganic bases include potassium carbonate and trisodiun phosphate. The base is used in an amount of fran about 1 to about 4 moles per mole of enol ester, preferably about 2 moles per mole. When the cyanide source is an alkali metal cyanide, particularly potassiun cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the Crown ethers. A nunber of different solvents may be usable in this process, depending on the nature of the acid chloride or the acylated product. A preferred solvent for this reaction is 1, 2-dichloooethane. Other solvents which may be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethyl formanide, and methyl isobutyl ketone (MIBK). In general, depending on the nature of the reactants and the cyanide source, the rearrangement may be conducted at temperatures up to about 50 C. The above described substituted bennoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L.F. Fieser and M. Fieser, pp. 767-769 (1967). EMI8.1 wherein R7 and R8 are as previously defined. The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C.A. Buehler and D.F. Pearson, J. Wiley and Sons, (1970). The following are three representative exules of the methods described therein. EMI8.2 wherein R7 and R8 are as previously defined. In reaction (a) the substituted bennonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. EMI9.1 wherein R7 and R8 are as previously defined. In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. EMI9.2 wherein R7 and R8 are as previously defined. In reaction (c) the substituted toluene is heated to reflux in an aqueous solution of potassiun permanganate for several hours. The solution is then filtered and the reaction product is isolated by conventional techniques. The following examples teach the synthesis of representative compounds of this invention. EXAMPLE 1 2-(2'-Nitrobenzoyl)-1,3-cyclohexanedione EMI9.3 2Hitrobenzoyl chloride (5.0 g, 27 mnol) and cyclohexanedione (3.0 g, 27 mnol) were dissolved in methylene chloride. Triethylanine (4.9 ml, 35 mnol) was added dropwise and the resulting solution stirred for one hour. The solution was washed with 2 normal hydrochloric acid (2N HCl), water, 5% potassiun carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under vacuum. The residue was dissolved in 20 ml acetonitrile. Triethylanine (1 equivalent) and potassium cyanide (40 mol %) were added and the solution stirred for one hour at roan temperature. After dilution with ether, the solution was washed with 2N HCl and extracted with 5% potassium carbonate solution. The aqueous extract was acidified and ether was added. Filtration of the resulting mixture yielded 3.2 g of the desired compound (m.p. 132-135iC) which was identified by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy. EXAMPLE 2 2-(2'-Nitrobenzoyl)-5,5-dimethyl-1,3-cyclohexanedione EMI10.1 Triethylanine (3.4 ml, 25 mmnl) was added dropwise to a methylene chloride solution of 2-nitooreooyl chloride (3.5 g, 19 mmol) and 5, 5-d imethylcyclohexanedione (2.4 g, 19 mrol). After stirring for one hour at roan temperature an additional 3 equivalents of triethylamine and 0.4 ml a acetone cyanonydrin were added. The solution was stirred for 2.5 hours, then washed with 2N ¯¯ and extracted with 5% potassiun carbonate solution. The e basic extracts were acidified with 2N HC1 and extracted with ether. The ether portion was washed with saturated sodiun chloride solution, dried over anhydrous magnesium sulfate and concentrated under vacuun. The residue was recrytallized from ethyl acetate yielding 2.0 g of the desired compound (m.p. 130-133 C) which was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy. The following is a table of certain selected compounds that are preparable according to the procedure described hereto. Compound nunbers are assigned to each canpound and are used throughout the remainder of the application. TABLE I EMI11.1 Comp. No. R1 Rê R3 R4 R5 R6 R7 R8 nD30 or m.p. 1 CH3 H H H H H H H viscous oil 2 CH3 CH3 H H CH3 H H H viscous oil 3a) H H H H H H H H 132-135 4 CH3 CH3 H H H H H H viscous oil 5b) H H CH3 CH3 H H H H 130-133 6 CH3 H H H CH3 H H H viscous oil 7 CH3 CH3 H H H H H CF3 52-61 8 H H H H H H H CF3 88-94 9 H H CH3 CH3 H H H cF3 3 89-97 10 CH3 CH3 H H H H 3-CH3 H 119-122 11 CH3 CH3 H H H H 3-Cl H 72-79 12 CH3 CH3 H H H H H Cl 118-121 13 CH3 CH3 H H H H 5-Cl H 118-120 14 CH3 CH3 H H H H 5-F H 130-133 15 CH3 CH3 H H H H 3-CH3O H H 139-142 16 CH3 CH3 CH3 H H H H CF3 viscous oil 17 CH3 CH3 H H H H H NO2 viscous oil 18 CH3 CH3 H H H H H Br viscous oil 19 CH3 CH3 H H H CH3 5-CH3 H viscous oil 20 CH3 CH3 H H H H 5-CH3 H viscous oil 21 H H H H H H H F 123-128 22 CH3 CH3 H H H H H F viscous oil 23 H H H H H H H Cl viscous oil 24 CH3 CH3 H H H H H SO2CH3 130-133 25 CH3 CH3 H H H H H SO2-n-C3H7 viscous oil 26 H H H H H H H SO2CH3 157-159 27 H H H H H H H SO2-n-C3H7 120-123 28 CH3 CH3 H H H H 5-F H 165-195 TABLE I (continued) EMI12.1 <tb> Come. <tb> <SEP> ND. <SEP> RL <SEP> Rz <SEP> R3 <SEP> R4 <SEP> R5 <SEP> R6 <SEP> R7 <SEP> R7 <SEP> R8 <SEP> nD30 <SEP> or <SEP> m.p. <tb> <SEP> 29 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> sO2-C2H5 <SEP> oil <tb> <SEP> 30 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> H <SEP> S02-CH3 <SEP> gum <tb> <SEP> 31 <SEP> CH3 <SEP> nrc4Rg <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> viscous <SEP> oil <tb> <SEP> 32 <SEP> H <SEP> H <SEP> i-C9 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> viscous <SEP> oil <tb> <SEP> 33 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> So2-c2E5 <SEP> vi <SEP> viscous <SEP> oil <tb> <SEP> 34 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> CN <SEP> viscous <SEP> oil <tb> <SEP> 35 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> SOaN(CH3)2 <SEP> 158-159 <tb> <SEP> 36 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> So2N(CH3)2 <SEP> 120-130 <tb> <SEP> 37 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> S02N(C2A5)2 <SEP> 158-163 <tb> <SEP> 38 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> sO2N(C2H5)2 <SEP> oil <tb> <SEP> CH3 <tb> <SEP> 39 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> SO2 <SEP> 4 <SEP> oil <tb> <SEP> n-C4H9 <tb> <SEP> 40 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> S 2-N(C2Hs)2 <SEP> oil <tb> <SEP> 41 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> SC2Hs <SEP> oil <tb> <SEP> 42 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> S(O)-nrC3H7 <SEP> oil <tb> <SEP> 43 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> S-nrc3H7 <SEP> oil <tb> <SEP> 44 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> H <SEP> S-n-C3H7 <SEP> oil <tb> <SEP> 45 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> S-n-C3H7 <SEP> oil <tb> <SEP> 46 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> H <SEP> S-C2H5 <SEP> oil <tb> <SEP> 47 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> S-C2H5 <SEP> oil <tb> <SEP> 48 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> S-CE3 <SEP> 94-97 <tb> <SEP> 49 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> H <SEP> CF3 <SEP> oil <tb> <SEP> 50 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> S-CH3 <SEP> oil <tb> <SEP> 51 <SEP> c) <SEP> H <SEP> i-C3H7 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 145-148 <tb> <SEP> 52 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 5-CH30 <SEP> Br <SEP> oil <tb> <SEP> 53 <SEP> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> Cl <SEP> oil <tb> <SEP> 54 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 3¯cm30 <SEP> Cl <SEP> oil <tb> <SEP> 55 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 3-CH30 <SEP> Cl <SEP> oil <tb> <SEP> 56 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> CH3 <SEP> H <SEP> H <SEP> CE3S <SEP> oil <tb> <SEP> H <tb> <SEP> 57 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 502N <SEP> 120-125 <tb> <SEP> n-C3H7 <tb> TABIE I (continued) Comp. No. R1 Rê R3 R4 R5 R6 R7 R8 nD30 or m.p. 58 H H CH3 CH3 H H H CN 175-177 59 CH3 CH3 H H H H H CN 151-153 60 CH3 CH3 H H CH3 H H CN oil 61 c) H H H H H H H oil 62 d) H H H H H H H oil 63 H H CH3 H H H H Cl 110-115 64 H H CH3 H H H H SO2-n-C3H7 oil 65 d) CH3 H H H H H Cl oil 66 H H H H H H H SO2CHCl2 oil 67 CH3 CH3 H H H H H SO2CHCl2 oil 68 H H H H H H c) Br oil 69 H H H H H H H SO2CH2Cl oil 70 CH3 CH3 H H H H H SO2CH2Cl wax 71 d) CE3 H H H H H H oil 72 H H H H H H C2H5O Cl oil 73 CH3 CH3 H H CH3 H CH30 CF3 oil a) Prepared in Example I. c) = b) Prepared in Example II. d) = i-C3H7OC(O)- Herbicidal Screening Tests As previously mentioned, the herein described compounds produced in the above-described manner are phytotoxic canpounds which are useful and valuable in controlling various plant species. Selected compounds of this invention were tested as herbicides in the following manner. Pre-emergence herbicide test. Cn the day preceding treatment, seeds of eight different weed species are planted in loany sand soil in individual rows using one species per row across the width of a flat. The seeds used are green foxtail (FT) (Setaria viridis), watergrass (WG) (Echinochloa crusgalli), wild oat (WO) (Avena fatua), annual morningglory (AMG) (Ipomoea lacunosa), velvetleaf (VL) (Abutilon theophrasti), Indian mustard (MD) (Brassica juncea), curly dock (CD) (Rumex crispus), and yellow nutsedge (YNG) (Cypers esculentus). Anple seeds are planted to give about -20 to 40 seedlings per row, after emergence, depending upon the size of the plants. Using an analytical balance, 600 milligrams (mg) of the compound to be tested are weighed out on a piece of glassine weighing paper. The paper and compound are placed in a 60 milliliter (ml) wide-motth clear bottle and dissolved in 45 ml of acetone or substituted solvent. Eighteen ml of this solution are transferred to a 60 ml wide-mouth clear bottle and diluted with 22 ml of a water and acetone mixture (19:1) containing enough polyoxyethylene sorbitan monolaurate emulsifier to give a final solution of 0.5% (v/v). The solution is then sprayed on a seeded flat on a linear spray table calibrated to deliver 80 gallons per acre (748 L/ha). The application rate is 4 lb/acre (4.48 Kg/ha). After treatment, the flats are placed in the greenhouse at a temperature of 70 to 80 F and watered by sprinkling. Two weeks after treatment, the degree of injury or control is determined by comparison with untreated check plants of the sane age. The injury rating from 0 to 100% is recorded for each species as percent control with 0% representing no injury and 100% representing complete control. The results of the tests are shown in the following Table II. TABLE II Pre-Emergence Herbicidal Activity Application Rate - 4.48 kg/ha Cmpd. No. FT WG WO AMG VL MD CD Yl 1 100 100 85 30 100 100 90 90 2 100 100 100 50 100 100 95 95 3 100 100 85 25 100 100 100 95 4 100 100 100 20 100 85 95 90 5 100 100 45 25 100 100 90 90 6 100 100 95 40 100 100 85 90 9 100 100 90 90 100 100 80 90 10 100 90 20 10 100 70 100 90 11 90 100 50 230 100 100 90 90 12 100 100 95 80 100 100 90 90 13 40 75 0 10 80 100 100 90 14 50 0 0 0 100 80 70 90 15 65 95 20 15 100 80 90 85 17 100 100 60 30 100 100 90 35 18 100 100 100 100 100 100 100 95 19 100 100 0 50 100 100 100 95 20 75 100 0 25 100 90 65 90 21 100 100 100 80 100 100 90 95 22 100 100 100 80 100 100 95 95 23 100 100 98 95 100 100 100 95 25 100 100 80 100 100 100 80 26 100 100 75 100 100 100 80 27 90 100 50 100 100 100 100 90 28 75 50 50 0 100 100 90 65 30 100 100 85 100 100 100 95 90 31 85 75 0 25 100 25 0 35 32 83 85 35 20 95 100 75 50 36 100 100 50 100 100 100 100 75 37 20 75 0 20 100 95 100 75 38 85 95 40 60 100 100 75 85 39 85 95 45 75 100 95 70 90 51 60 60 35 0 25 0 0 30 52 75 75 0 50 90 75 40 0 65 100 100 80 100 100 100 - 80 A blank (-) indicates that the weed was not tested. Post-Emergence Herbicide Test: This test is conducted in an identical manner to the testing procedure for the pre-emergence herbicide test, except the seeds of the eight different weed species are planted 1012 days before treatment. Also, watering of the treated flats is confined to the soil surface and not to the foliage of the sprouted plants. The results of the post-nergence herbicide test are reported in Table III. TABLE III Post-Emergence Herbicidal Activity Application Rate - 4.48 kg/ha Cmpd. No. FT WG WO AMG VL MD CD YNG 1 95 75 85 70 100 90 85 40 2 45 70 95 75 100 90 100 65 3 100 80 100 90 - 100 100 80 4 100 80 100 100 - 100 85 75 5 90 70 45 60 95 70 60 80 6 95 75 80 70 100 90 90 65 9 100 90 90 100 100 100 95 85 10 45 75 10 15 100 100 20 75 11 100 70 60 75 100 100 100 45 12 100 75 100 100 100 100 90 90 13 30 55 0 30 60 60 15 60 14 20 65 0 40 70 60 40 25 15 20 75 30 20 100 70 60 40 17 85 80 50 65 95 95 100 60 18 100 95 100 100 100 100 100 75 19 20 95 30 100 100 35 30 70 20 30 80 15 100 100 45 20 70 21 100 80 100 55 100 90 100 80 22 100 80 100 60 100 95 95 95 23 100 90 90 100 100 100 85 70 25 70 75 50 85 90 85 60 75 26 100 85 85 95 95 95 90 60 27 90 90 60 100 100 100 100 28 15 45 20 50 75 80 15 30 30 100 100 80 85 85 85 100 31 80 90 100 100 100 100 100 60 32 75 85 85 75 75 90 95 50 36 35 50 35 70 50 50 35 60 37 60 75 15 70 70 90 90 40 38 95 90 65 70 90 90 100 50 39 95 85 30 50 70 80 100 50 51 60 75 60 35 30 60 40 60 52 60 75 25 100 100 100 100 75 65 70 50 70 90 80 85 - 80 A blank (-) indicates the weed was not tested. Pre-Emergence Multi-Weed Herbicide Test Several compounds were evaluated at an application rate of 2, 1, 1/2 or 1/4 lb/acre (2.24, 1. 12, 0.56 or 0.28 kg/ha) for pre-emergence activity against a larger number of weed species. The e process was generally similar to the pre-emergence herbicide test described above except that only 300, 150, 75 or 37.5 milligrams of test compound were weighed out and the application rate was 40 gallons per acre. Redroot pigweed (PW) and curly dock (CD) were eliminated in this test and the following weed species were added: Grasses: downy brane Bromus tectorum (DB) annual ryegrass Lolium multiflorum (ARG) shattercane Sorghum bicolor (SBC) hemp sesbania Sesbania exaltata (SESB) sickepod Cassia obtusifolia (SP) cocklebur Xanthium sp. (CB) broadleaf signalgrass ENrachiaria platyphylla (BSG) The results of the test are shown in Tables IV, V and VI. ABLE IV Pre-Emergence Multi-weed Herbicide Test Application Rate - 2.24 kg/ha Qnpd. No. DB FT ARG WG SHC WO BSG AMG SESB VL SP MD YNG CB 7 100 100 100 100 100 100 100 100 100 100 100 100 95 100 8 100 100 100 100 100 100 100 100 100 100 100 100 95 16a 70 100 65 100 100 60 98 55 100 100 90 100 90 24 100 100 100 100 100 100 100 100 100 100 100 100 100 29 100 100 100 100 100 100 100 100 100 100 30 100 95 80 33 75 15 60 90 90 20 95 100 100 100 60 100 95 100 53 100 100 100 100 100 90 100 100 100 100 100 100 95 100 57 100 100 25 100 100 30 25 100 100 100 100 100 95 100 64a ¯ 0 0 95 35 0 15 50 75 75 25 - 75 40 66a ¯ 0 15 15 50 20 50 100 100 75 0 - 90 100 67a - 0 0 100 100 0 25 95 75 50 25 - 30 75 69a - 30 0 100 100 0 70 100 100 100 35 - 95 100 70a - 100 10 100 100 25 65 100 100 100 0 - 95 100 (-) = Not tested. (a) - Tested at 0.28 kg/ha. TABLE V Pre-Emergence Multi-weed Herbicide Test Application Rate - 1.12 kg/ha Onpd. No. DB FT ARG WG SHC WO BSG AMG SESB VL SP MD YNG CB 34 90 85 30 95 - 45 98 75 100 100 40 100 50 35 100 85 70 100 - 90 100 100 100 100 40 100 75 40 100 100 20 100 - 70 100 98 98 100 20 100 50 41 100 100 80 100 - 60 100 100 100 100 25 100 95 42 50 60 40 85 - 30 100 100 100 100 100 100 90 43 90 95 60 100 - 30 98 100 98 100 45 100 95 44 60 100 20 100 - 60 100 100 90 100 20 100 80 45 95 100 35 100 - 60 90 100 100 100 0 100 90 46 100 100 90 100 - 95 100 100 100 100 40 100 95 47 100 100 100 100 - 98 100 100 98 100 30 100 95 48 100 100 100 100 - 100 100 100 100 100 90 100 100 49 100 100 100 100 - 100 100 100 100 100 90 100 - 50 100 100 100 100 100 85 100 100 100 100 90 100 98 54 100 100 85 100 100 15 100 25 100 100 65 100 95 100 55 85 100 35 100 98 15 100 15 100 100 65 100 95 56 100 100 100 100 100 100 100 100 100 100 100 100 100 100 58 98 100 40 95 40 20 95 100 100 100 85 100 100 95 59 100 100 100 100 100 90 100 100 100 100 100 100 85 80 60 100 100 100 100 100 100 100 100 100 100 75 100 85 80 (-) = Not tested. TABLE VI Pre-Emergence Multi-weed Herbicide Test Application Rate - 0.56 kg/ha Cmpd. EB FT ARG WG SEC WO BSG AMG SESB VL SP MD YNG (3 61 - 100 65 100 65 20 80 20 40 80 10 - 20 0 62 - 50 35 70 50 0 0 0 25 50 0 - 0 0 63 100 100 100 100 100 95 100 90 95 100 75 100 100 85 68 - 0 20 0 0 0 0 60 100 100 90 - 75 75 71 - 50 40 50 75 40 35 75 50 70 0 - 75 75 72 - 35 60 100 85 50 100 25 65 100 35 - 100 35 73 - 90 70 100 95 25 0 70 100 100 0 - 50 25 (-) = Not tested. Post-Emergence Multi-weed Herbicide Test: This test is conducted in an identical manner to the testing procedure for the postemergence herbicide test, except the seeds of the eight weed species used in the pre-emergence multi-weed herbicide test were used ard the seeds were planted 10-12 days before treatment. Also, watering of the treated flats is confined to the soil surface and not to the foliage of the sprouted plants. The results of the post-emergence multi-weed herbicide test are reported in Tables VII, VIII and IX. TABLE VII - V C Post-Emergence Multi-Weed Herbicidal Activity application Rate - 2.24 kg/ha Qnpd. No. DB FT ARG WG SHC WO BSG AMG SESB VL SP MD YNG CB 7 100 100 100 100 80 90 10 95 100 100 55 100 45 100 16a 100 85 35 100 100 100 100 100 100 100 100 100 85 70 24 100 100 100 100 100 100 100 100 100 100 100 100 100 29 100 100 60 100 90 100 100 100 100 100 100 100 100 33 90 98 85 100 100 80 100 100 100 100 90 100 90 100 53 100 100 60 100 100 100 100 100 100 100 100 100 100 57 25 40 10 100 10 0 10 100 95 100 35 100 - 100 64a - 0 0 90 0 0 85 40 100 80 50 - 35 100 66a ¯ 0 0 65 0 0 70 75 80 75 0 - 25 75 67a ¯ 0 0 75 35 0 40 70 80 60 0 - 0 100 69a ¯ 0 0 80 35 0 100 90 100 100 40 - 35 100 70a - 100 0 100 70 90 90 100 100 100 30 - 25 100 (-) = Not tested. (a) = Tested at 0.28 kg/ha. TABLE VIII Post-Emergence Multi-weed Herbicide Test Application Rate - 1.12 kg/ha Cppd. No. DB FT ARG WG SEC we BSG AMG SESB VL SP MD YNG CB 34 90 85 30 95 - 45 98 75 100 100 40 100 50 35 100 85 70 100 - 90 100 100 100 100 40 100 75 40 75 100 5 100 - 50 75 100 100 100 40 100 30 41- - - - - - - - - - - - - - - 42 40 100 35 100 - 50 80 100 100 100 80 100 70 43 60 70 20 100 - 55 60 100 100 100 95 100 70 44 - - - - - - - - - - - - - 45 -. - - - - - - - - - - - - - 46 - - - - - - - - - - - - - 47 90 100 35 100 - 75 90 100 100 100 25 100 45 48 80 100 60 100 - 60 80 100 100 100 85 100 60 49 - - - - - - - - - - - - - 50 90 80 60 95 80 90 100 100 100 100 65 100 80 54 35 50 30 100 30 15 90 100 100 100 100 100 95 55 100 100 20 100 90 20 100 90 100 100 100 100 - 56 75 90 75 95 90 25 100 100 100 100 90 100 90 100 58 70 100 40 100 95 30 95 100 95 100 95 100 95 85 59 90 100 95 100 100 50 100 100 100 100 95 100 100 95 60 95 100 100 100 100 75 95 100 100 100 95 100 100 100 (-) = Not tested. TABLE IX Post-Emergence Multi-weed Herbicide Test Application Rate - 0.56 kg/ha Cmpd. No. DB FT ARG WG SHC WO BSG AMG SESB VL SP MD WG CB 61 - 40 0 50 35 0 40 75 95 100 0 - 25 50 62 - 35 0 20 0 0 20 35 60 100 0 - 0 100 63 100 100 85 98 85 100 100 100 100 100 100 85 85 95 68 - 30 40 85 0 25 60 80 95 100 95 - 0 80 71 - 50 0 80 65 0 75 100 80 100 50 - 25 100 72 - 90 70 80 50 50 75 - 85 100 100 90 - 100 100 73 -100 15 100 75 75 85 100 100 90 60 - 80 100 (-) = Not tested. The canponds of the present invention are useful as herbicides and can be applied in a variety of ways at various concentrations. In practice, the compounds herein defined are formulated into herbicidal compositions, by mixture, in herbicidally effective amounts, with the ad; w ants and carriers normally employed for facilitating the dispersion of active ingredients for agricultural applications, recognizing the fact that the formulation and mode of application of a toxicant may affect the activity of the materials in a given application. Thus, these active herbicidal canpounds may be formulated as granules of relatively large particle size, as wettable powders, as emulsifiable concentrates, as pow- dery dusts, as solutions or as any of several other known types of formulations, depending upon the desired mode of application. Preferred formulations for pre-nergence herbicidal applications are wettable powders, emulsifiable concentrates and granules. These formulations may contain as little as about 0.5% to as much as about 95% or more by weight of active ingredient. A herbicidally effective amount depends upon the nature of the seeds or plants to be controlled and the rate of application varies from about 0.05 to approximately 25 pounds per acre, preferably from about 0.1 to about 10 pounds per acre. Wettable powders are in the form of finely divided particles which disperse readily in water or other dispersants. The wettable powder is ultimately applied to the soil either as a dry dust or as a dispersion in water or other liquid. Typical carriers for wettable powders include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic diluents. Wettable powders normally are prepared to contain about 5% to about 95% of the active ingredient and usually also contain a small amount of wetting, dispersing, or emulsifying agent to facilitate wetting and dispersion. Emulsifiable concentrates are homogeneous liquid compositions which are dispersible in water or other dispersant, and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aranatic naphthal, isophorone and other non-volatile organic solvents. Fbr 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 weight of the essential active ingredient may vary according to the manner in which the composition is to be applied, but in general comprises about 0.5% to 95% of active ingredient by weight of the herbicidal composition. Granular formulations wherein the toxicant is carried on relay tively coarse particles, are usually applied without dilution to the area in which suppression of vegetation is desired. Typical carriers for gran ular formulations include sand, fuller's earth, bentonite clays, vermiculite, perlite and other organic or inorganic materials which absorb or which may be coated with the tcsicant. Granular formulations normally are prepared to rontain about 5% to about 25% of active ingredients which may include surface-active agents such heavy aranatic naphthas, kerosene or other petroleum fractions, or vegetable oils; and/or stickers such as destrins, glue or synthetic resins. Atypical wetting, dispersing or emulsifying agents used in agri cultural 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 come merce. The surface-active agent, when used, normally comprises from 0.1% to 15% by weight of the herbicidal composition. Dusts, which are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers for the toxicant, are useful formulations for soil-incorporating application. Pastes, which are homogeneous suspensions of a finely divided solid toxicant in a liquid carrier such as water or oil, are employed for specific purposes. These formulations normally contain about 58 to about 95% of active ingredient by weight, and may also contain snaIl amounts of a wetting, dispersing or emulsifying agent to facilitate dispersion. Ebr application, the pastes are normally diluted and applied as a spray to the area to be affected. Other useful formulations for herbicidal applications 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 and other organic solvents. Pressurized sprays, typically aerosols, wherein the active ingredient is dispersed in finelydivided form as a result of vaporization of a low boiling dispersant solvent carrier, such as the Freons, may also be used. The phytotoxic canpositions of this invention are applied to the plants in the conventional manner. Ihus, the dust and liquid compositions can be applied to the plant by the use of power-dusters, boam and hand sFrayers and spray dusters. The canpositions can also be applied fran airplanes as a dust or a spray because they are effective in very low dosages. In order to modify or control growth of germinating seeds or emerging seedlings, as a typical example, the dust and liquid ccmpositions are applied to the soil according to conventional methods and are distributed in the soil to a depth of at least 1/2 inch be w the soil surface. It is not necessary that the phytotoxic compositions be admixed with the soil particles since these compositions can also be applied merely by straying or sprinkling the surface of the sol. The phytotoxic composi- tioris of this invention can also be applied by addition to irrigation water supplied to the field to be treated. this method of application permitS the penetration of the compositions into the soil as the water is absorbed therein. Dust compositions, granular compositions or liquid formulations applied to the surface of the soil can be distributed below the surface of the soil by conventional means such as discing, dragging or mixing operations. EMULSIFIABLE CONCENTRATE FORMULATIONS General Formula with nges Specific Formula Herbicidal compound 5-55 herbicidal compound 54 surfactant(s) 5-25 proprietary blend of oil- 10 solvent( s) 20-90 soluble sulfonates and 100% polyoxyethylene ether polar solvent 27 petroleun hydrocarbon 9 WETTABLE POWDER FORMULATIONS herbicidal compound 3-90 herbicidal compound 80 wetting agent 0.5-2 sodiun dialkyl naphthalene 0.5 dispersing agent 1-8 sulfonate diluent(s) 8.5-87 sodium lignosulfonate 7 100% attapulgite clay 12.5 100% EXTRUDED GRANULAR FORMULATIONS herbicidal compound 1-20 herbicidal compound 10 binding agent 0-10 lignin sulfonate 5 diluent(s) 70-99 calcium carbonate 85 100% 100% FLOWABLE FORMULATIONS herbicidal compound 20-70 herbicidal compound 45 surfactant(s) 1-10 polyoxyethylene ether 5 suspending agent(s) 0.05-1 attagel 0.05 antifreeze agent 1-10 propylene glycol 10 antimicrobial agent 1-10 BIT 0.03 antifoam agent 0.1-1 silicone defoaner 0.02 solvent 7.95-77.85 water 39.9 100% 100% The phytotoxic canpositions of this invention can also contain other additanents, for exanple, fertilizers and other herbicides, pesticides and the like, used as adjuvant or in combination with any of the abcre-described adj uvants. Other phytotoxic canpounds useful in combina- tion with the above-described compounds include, for exanple, anilides such as 2-benzothiazole-2-yloxy-N-methyl acetanilide, 2-chloro-2',6'-dimethyl-N-(n-propylethyl) acetanilide, 2-chloro-2',6'-diethyl-N-(butoxymethyl) acetanilide; 2,4-dichlorophenoxyacetic acids, 2,4,5-trichlorophenoxyacetic acid, 2-methyl-4 -diloroFhenoxyacetic acid and the salts, esters and anides thereof; triazine derivatives, such as 2,4-bis(3-methoxypropyl- amino)-6-methylthio-s-triazine, 2-chloro-4-ethylamino-6-isopropylamino-striazine, and 2-ethylamino-4-isopropyl-amino-6-methyl-mercapto-s-triazine; urea derivatives, such as 3-(3,5-dichlorophenyl)-1,1-dimethylurea and 3-(p-chlorophenyl)-1,1-dimethylurea; and acetanides such as N,N-diallyl- &alpha;-chloroacetamide, and the like; benzoic acids such as 3-amino-2,5-di- chlorobenzoic acid; thiocarbanates such as S-(1,1-dimethylbenzyl)-piperidene-1-carbothioste, 3-(4-chlorophenyl)-methyl diethylcarbothioate, ethyl-l -hexahydro-l ,4-a zepine-1 -carbothioate, S-ethyl-hex ahydro- 1H-a ze- pine-1 -carbothioate, S-propyl N,N-dipropylthiocarbamate, S-ethyl N,N-dipropylthiocarbamate, S-ethyl cyclohexylethylthiocarbanate and the like; anilines such as 4-(methylsulfonyl)-2,6-dinitro-N,N-substituted aniline, 4-trifluoromethyl-2,6-dinitro-N,N-dipn-propyl aniline, 4-trifluoromethyl2,6-dinitro-N-ethyl-N-butyl aniline, 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid, 2-[1-(ethoxyimino)butyl]-5-[2-ethylthio)propyl]-3-hydroxy2-cyclohexene-1-one, (#)-butyl-2-[(5-trifluoromethyl)-2-pyridinyl)oxy]- phenoxy]propanate, sodium 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, 3-isopropyl-1H-2,1,3-benzothiadiazine-4(3H)-one-2,2-dioxide, and 4-amino-6-tert-butyl-3(methylthio)-as-triazin-5(4g)-one or 4-anino-6- (1,1 - dimethylethyl) -3-(methylthio)-7, 2, 4-triazin-5 (4R)-one and S-(O,O-diisopropyl)-benzene sulfonanide. Fertilizers useful in combination with the active ingredients include, for example, ammonium nitrate, urea and super- phosphate. other useful additanents include materials in which plant organisms take root and grow such as canpost, manure, hunus, sand, and the like.

Claims: WHAT IS CLAIMED IS: 1. A corçotnd of the formula EMI27.1 wherein R1 is hydrogen or C1-C4 alkyl; R2 is hydrogen, C1-C4 alkyl or EMI27.2 wherein Ra is C1-C4 alkyl; or R1 and R2 together are alkylene having 3 to 6 carbon atoms; R3 is hydrogen or C1-C4 alkyl; R4 is hydrogen or C1-C4 alkyl; R5 is hydrogen or C1-C4 alkyl; R6 is hydrogen or C1-C4 alkyl; and R7 and R8 independently me (1) hydrogen; (2) halogen; (3) C1-C4 alkyl; (4) C1-C4 alkoxy; (5) OCF3; (6) cyano; (7) nitro; (8) C1-C4 haloalkyl; (9) RbSOn- wherein n is the integer 0, 1 or 2; and Rb is (a) C1-C4 alkyl; (b) C1-C4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) -NRCRd wherein RC and Rd independently are hydrogen or C1-C4 alkyl; (11) ReC(O)- wherein Re is C1-C4 alkyl or C1-C4 alkoxy; or (12) SO2NRCRd wherein RC and Rd are as defined, with the proviso that R7 is not attached to the 6-position. 2. The compounds of Claim 1 wherein R1 is hydrogen or methyl; R2 is hydrogen or methyl; R3 is hydrogen or methyl; R4 is hydrogen or methyl; R5 is hydrogen or methyl; R6 is hydrogen or methyl; R7 and R8 independently are (1) hydrogen; (2) halogen; (3) C1-C4 alkyl; (4) C1-C4 alkoxy; (5) OCF3; (6) cyano; (7) nitro; (8) C1-C4 haloalkyl; (9) RbSOnwherein n is the integer 0, 1 or 2; and Rb is (a) C1-C4 alkyl; (b) C1-C4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) -NRCRd wherein Rc and Rd independently are hydrogen or C1-C4 alkyl; (11) ReC(O)- wherein Re is C1-C4 alkyl or C1-C4 alkoxy; or (12) SO2NRcRd where- in Rc and Pd are as defined. 3. The compound of Claim 2 wherein R7 and R8 are independently are hydrogen; chlorine; fluorine; branine; methyl; methoxy; OCF3; cyano; nitro; trifluoromethyl; RbSOn- wherein n is the integer 2 and Rb is methyl, chloromethyl, trifluoranethyl, cyanomethyl, ethyl, or n-propyl; -NRcRd wherein Rc and Rd independently are hydrogen or C1-C4 alkyl; ReC(O)- where five is C1-C4 alkyl or C1-C4 alkoxy or SO2NRCRd wherein Rc and are as defined and R7 is in the 3-position. 4. The compound of Claim 2 wherein R7 is hydrogen and R8 is hydrogen, chlorine, bromine, fluorine, CF3 or RbSO2 wherein Rb is C1-C4 alkyl or C1-C4 haloalkyl. 5. The compound of Claim 2 wherein R1 is methyl; R2 is methyl; R3 is hydrogen; R4 is hydrogen; R5 is hydrogen; R6 is hydrogen; R7 is hydrogen; and R8 is hydrogen. 6. The compound of Claim 2 wherein R1 is methyl; R2 is methyl; R3 is hydrogen; R4 is hydrogen; R5 is methyl; R6 is hydrogen; R7 is hydrogen; and R8 is hydrogen. 7. The e compound of Claim 2 wherein R1 is methyl; R2 is methyl; R3 is hydrogen; R4 is hydrogen; R5 is hydrogen; R6 is hydrogen, R7 is hydrogen; and R8 is trifluoromethyl. 8. The compound of Claim 2 wherein R1 is hydrogen; R2 is hydrogen; R3 is hydrogen; R4 is hydrogen; R5 is hydrogen; R6 is hydrogen; R7 is hydrogen; and R8 is trifluoromethyl. 9. The compound of Claim 2 wherein R1 is methyl; R2 is methyl; R3 is hydrogen; R4 is hydrogen; R5 is hydrogen; R6 is hydrogen; R7 is hydrogen; and R8 is chlorine. 10. The compound of Claim 2 wherein R1 is methyl; R2 is methyl; R3 is hydrogen; R4 is hydrogen; R5 is hydrogen; R6 is hydrogen; R7 is hydrogen; and R8 is fluorine. 11. The oompound of Claim 2 wherein R1 is hydrogen; R2 is hydrogen; R3 is hydrogen; R4 is hydrogen; R5 is hydrogen; R6 is hydrogen; R7 is hydrogen; and R8 is chlorine. 12. The e compound of Claim 2 wherein R1 is methyl; R2 is methyl; R3 is hydrogen; R4 is hydrogen; R5 is hydrogen; R6 is hydrogen; R7 is hydrogen; and R8 is CH3SO2-. 13. The compound of Claim 2 wherein R1 is hydrogen; R2 is hydrogen; R3 is hydrogen; R4 is hydrogen; R5 is hydrogen; R6 is hydrogen; R7 is hydrogen; and R8 is n-C3H7SO2. 14. The compound of Claim 2 wherein R1 is hydrogen; R2 is hydrogen; R3 is hydrogen; R4 is hydrogen; R5 is hydrogen; R6 is hydrogen; R7 is hydrogen; and R8 is CH3SO2. 15. The compound of Claim 2 wherein R1 is hydrogen; R2 is hydrogen; R3 is hydrogen; R4 is hydrogen; R5 is hydrogen; R6 is hydrogen; R7 is hydrogen; and R8 is C2B58o2. 16. The compounds of Claim 2 wherein R7 is hydrogen. 17. The compounds of Claim 3 wherein R7 is hydrogen. 18. The carpound of Claim 2 wherein R1 is hdyrogen; R2 is hydrogen; R3 is hydrogen, R4 is hydrogen; R5 is hydrogen; R6 is hydrogen; R7 is hydrogen; and R8 is cyano. 19. The compound of Claim 1 wherein R1 and R2 are hydrogen or both methyl. 20. The compound of Claim 49 wherein R8 is -S02CH3. 21. The compound of claim 19 wherein R8 is -S02CH2C1. 22. The compound of CLaim 1 wherein R8 is 23. The compound of Claim 1 wherein R8 is -SO2CH3. 24. The compound of Claim 1 wherein R8 is chlorine. 25. The compound of Claim 1 wherein R8 is -SO2CH2Cl. 26. The compound of Claim 1 wherein R8 is -SO2-n-C3H7. 27. The e method of controiling undesirable vegetation comprising applying to the area where control is desired, an herbicidally effective amount of a compound described in Claims 1-26. 28. An herbicidal composition comprising an herbicidally active 2-(2-nitrobenzoyl)-1,3-cyclohexanedione and an inert carrier therefor. 29. The herbicidal wsition of Claim 28 wherein the 2-(2-nitrobenzoyl)-1,3-cyclohexanedione is a compound of Claims 1-26. 30. The method of controlling undesirable vegetation comprising applying to the area where control Xs desired, an herbicidal composition comprising an herbicidally active 2-(2-nitrobenzoyl)-1,3-cyclohexanedione and an inert carrier therefor. 31. The method of Claim 30 wherein the 2-(2-nitrobenyl)-1,3- cyclohexanedione has a C1-C4 alkylsulfonyl or C1-C4 haloalkylsulfonyl substitution on the phenyl ring. 32. The method of Claim 31 wherein said alkylsulfonyl or halo alkylsulfonyl substitution is at the 4-position of the phenyl ring. 33. The herbicidal composition of Qiam 28 wherein the 2-(2-nitrobenzoyl)-1,3-cyclohexanedione has a C1-C4 alkylsulfonyl or C1"C4 haloalkylsulfonyl substutition on the phenyl ring. 34. The herbicidal composition of Claim 32 wherein said alkylsulfonyl or haloalkylsulfonyl substitution is at the 4-position of the phenyl ring. 35. The method of Claim 30 wherein the 2-(2-nitrobenzoyl)-1,3- cyclohexanedione has a C1-C4 haloalkyl substitution on the phenyl ring. 36. The method of Claim 30 wherein said haloalkyl substitution is at the 4-position on the phenyl ring. 37. The herbicidal composition of Claim 28 wherein the 2-(2nitrobenzoyl)-1,3-cyclohexanedione has a C1-C4 haloalkyl substitution on the phenyl ring. 38. The herbicidal composition of Claim 37 wherein said haloalkyl substitution is at the 4-position of the phenyl ring. 39. The herbicidal canposition of Claim 37 wherein said haloalkyl is CF3. 40. The method of Claim 35 wherein said haloalkyl is CF3. 41. The method of Claim 27 wherein R1 and R2 are hydrogen or both methyl. 42. The method of Claim 41 wherein R8 is -SO2CH3, -S02CH2C1, CF3, -SO2CH3, chlorine, -SO2CH2Cl or -SO2-n-C3H7. 43. The composition of matter of Claim 28 wherein R1 and R2 are hydrogen or both methyl. 44. The composition of matter of Claim 43 wherein R8 is -SO2CH3, -SO2CH2Cl, CF3, -SO2CH3, chlorine, -SO2CH2Cl or -SO2-n-C3H7. 45. A process for preparing a compound of the formula EMI32.1 wherein R1 is hydrogen or C1-C4 alkyl; R2 is hydrogen, C1C4 alkyl or EMI32.2 wherein Ra is C1-C4 alkyl; or R1 and R2 together are alkylene having 3 to 6 carbon atoms; R3 is hydrogen or C1-C4 alkyl; R4 is hydrogen or C1-C4 alkyl; R5 is hydrogen or C1-C4 alkyl; R6 is hydrogen or Cr-C4 alkyl; and R7 and R8 independently are (1) hydrogen; (2) halogen; (3) C1-C4 alkyl; (4) C1-C4 alkoxy; (5) OCF3; (6) cyano; (7) nitro; (8) C1-C4 haloalkyl; (9) RbSOn- wherein n is the integer 0, 1 or 2; and Rb is (a) C1-C4 alkyl; (b) C1-C4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) -NRCRd wherein Rc and Rd independently are hydrogen or C1-C4 alkyl; (11) ReC(O)- wherein Re is C1-C4 alkyl or C1-C4 alkoxy; or (12) SO2NRcRd wherein Rc and Rd are as defined, with the proviso that R7 is not attached to the 6-position comprising (a) reactinq a dione of the formula EMI33.1 wherein R1 through R6 are as defined with a substituted benzoyl reactant of the formula EMI33.2 wherein R7 and R8 are as defined and X is halogen, C1 -C4 alkyl-C(O)-O-, C1-C4 alkoxy-C(O)-O- or EMI33.3 wherein R7 and R8 in this portion of the molecule are identical with those in the reactant shown above with at least a mole of a moderate base to fran an enol ester of the formula EMI33.4 wherein R1 through R8 are as defined and in step (2) reacting a mole of the enol ester intermediate with 1 to 4 moles of a moderate base, and from 0.01 mole to about 0.5 mole or higher of a cyanide source to form a com, pound Ot the formula EMI34.1 wherein R1 through R8 are as defined above. 46. The process of Claim 45 wherein X is halogen, the moderate base is tri-C1-C6 alkylanine, pyridine, alkali metal carbonate or alkali metal phosphate and the cyanide source alkali metal cyanide, cyanohydrins of methyl C1-C4 alkyl ketones, cyanohydrins of benzaldehyde or C2-Cs aliphatic aldehydes; cyanohydrins, zinc cyanide; tri(lower alkyl) silyl cyanides or hydrogen cyanide. 47. The process of Claim 46 wherein X is chlorine, the moderate base is tri-Cl-C6 alkylanine, pyridine, sodiun carbonate or sodium phosphate and the cyanide source is potassium cyanide, acetone cyanchydrin or hydrogen cyanide.

Inventors: CARTER, CHARLES GARVIE
Applicants: STAUFFER CHEMICAL COMPANY
Application year: 1985
Main classification: C07C205
IPC codes: C07C317, C07C49, A01N37, C07C303, C07C225, C07C67, A01N35, C07C323, A01N47, C07C229, C07C227, C07C311, C07C255, A01N41, C07C201, C07C205, C07C301, A01P13, C07C213, C07C313