CERTAIN 2-(2-SUBSTITUTED BENZOYL)-1,3-CYCLOHEXANEDIONES

Abstract: Compounds having the structural formula wherein R and R¹ are hydrogen, C₁-C₄ alkyl, R a OC(O)-, where R a is C₁-C₄ alkyl; R² is chlorine, bromine, iodine or C₁-C₄ alkoxy; and R³, R⁴ and R⁵ independently are hydrogen or an aliphatic group.

Description: CERTAIN 2-(2-SUBSTITUTED BENZOYL)-1,3-CYCLOHEXANEDIONES Cross-ference to Pelated Applications This application is a continuation-in-part application of Serial No. 587,331, filed March 7, 1984; which in turn is a continuation-in-part of application Serial tt. 532,869, filed September 16, 1983; which in turn is a continuation-inpart application of 464,251, filed February 9, 1983, row abandoned which in turn is a continuation-in-part application of Serial No. 361,658, filed March 25, 1982, now abandoned. 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 alkynyl. 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-chlorDphenyl or 4-methcocyphenyl. The precursor intermediates for these three specifically taught compounds have no or almost no herbicidal activity. In contrast, the canpounds of this invention have exceptional herbicidal activity. Applicant's compounds must have a chlorine, branine, iodine or alkoxy substitution in the 2-position of the phenyl moiety of their canpounds to obtain the exceptional herbicidal activity. Chlorine is the preferred substituent. The exact reason why such a substitution imparts exceptional herbicidal activity to the compound is not fully understood. Description of the Invention This invention relates to certain novel 2-(2-substituted benzoyl)-cyclohexane-1,3-diones as herbicides. The canpounds of this invention have the following structural formula EMI2.1 wherein R and R1 are hydrogen, C1 alkyl, preferably methyl or iso- propyl, RaOC(C)-, where Ra is C1-C4 alkyl; most preferably R and R1 are hydrogen; R2 is chlorine, branine, iodine or C1-C4 alkoxy, preferably methoxy; most preferably R2 is chlorine, branine or methoxy; R3, R4 and R5 independently are hydrogen or an aliphatic group, preferably: (1) hydrogen; (2) halogen, preferably chlorine or branine; (3) C1-C4 alkyl, preferably methyl; (4) C1-C4 alkoxy, preferably methoxy; (5) ocF3; (6) cyan; (7) nitro; (8) C1-C4 haloalkyl, more preferably trifluoranethyl; (9) RbSOn- wherein Rb is C1-C4 alkyl, preferably methyl, C1-C4 haloalkyl, phenyl, benzyl, ZNRdRe wherein Rd and Re independently are hydrogen or C1-C4 alkyl; and n is the integer 0, 1 or 2, preferably 2; EMI2.2 wherein RC is C1-C4 alkyl, (11) RfC(O) wherein Rf is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy; (12) RRh wherein Rg and pendently are hydrogen or C1-C4 alkyl; or less preferably (13) R3 and R4 index together can form a ring structure with two adjacent carbon atans of the phenyl ring. Most preferably, R3 is chlorine, hydrogen, dimethylanino or methoxy. Preferably R4 is hydrogen, chlorine, nitro, SO2CH3, SO2N (CH3)2 or CF3. Preferably, R5 is hydrogen. The canpounds of this invention can have the following four structural formulae because of tautomerism : EMI3.1 wherein R, R1, R2, R3, R4 and R5 are as defined above. The circled proton on each of the four tautaners is reasonably labile. The Protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: EMI3.2 wherein R, R1, R2, R3, R4 and R5 are as defined above. Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodium, and potassium alkaline earth metals, e.g. bariun, magnesium, cAlcium and strontiun or organic cations such as substituted ammonium, sulfoniun or phosphoniun wherein the substituted is an aliphatic or aromatic group. The term "aliphatic group" is used herein in a broad sense to cover a large class of organic groups characterized by being derived fran (1) an acylic (open-chain structure) of the paraffin, olefin and acetylene hydrocarbon series and their derivatives or (2) alicyclic canpounds. The aliphatic group can have fran 1 to 10 carbon atans. The term waramatic group" is used herein in a broad sense to distinguish from the aliphatic group and includes a group derived from (1) canpounds having 6 to 20 carbon atans and characterized by the presence of at least one benzene ring, including monocyclic, bicyclic and polycyclic hydrocarbons and their derivatives and (2) heterocyclic compounds having 5 to 19 carbon atoms which are similar in structure and are characterized by having an unsaturated ring structure containing at least one atom other than carbon such as nitrogen, sulfur and oxygen and derivatives of these heterocycl ic cawounds. In the above description of the canpounds of this invention alkyl and alkoxy include both straight and branched configurations, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl. The canpounds of this invention and their salts are active herbicides of a general type. That is, they are herbicidally effective against a wide range of plant species. The method of controlling undesirable vegetation of the present invention canprises applying an herbicidally effective amount of the above-described canpounds to the area where control is desired. The compounds of the present invention can be Erepared by the followirg general method. EMI5.1 Generally, mole amounts of the dione and substituted henzoyl cyanide are used, along with a slight mole excess of zinc chloride. The two reactants ard the zinc chloride are canbined in a solvent such as methylene chloride. A slight mole excess of triethylanine is slowly added to the reaction mixture with cooling. The mixture is stirred at roan temperature for 5 hours. The reaction product is worked up by conventional techniques. The above-described substituted benzoyl cyanide can be prepared according to the teaching of T.S. Cakood and C.A. Weisgerber, Organic Synthesis Collected, . III, pp. 122 (1955). The following exanple teaches the synthesis of a representative compound of this invention. EXAMPLE I 2-(2,4-Dichlorobenzoyl)-cyclohexane-1,3-dione EMI5.2 1,3-Cyclohexanedione [11.2 grans (g), 0.1 mole], 20.0 g (0.1 mole) 2,4-dichlorobenzoyl cyanide and 13.6 g (O.11 mole) anhydrous, pow dered zinc chloride were canbined in 100 milliliters (ml) methylene chloride. Triethylamine (10.1 g, 0.12 mole) was slowly added with cooling. The reaction mixture was stirred at rocm temperature for 5 hours and then poured into 2N hydrochloric acid. The aqueous phase was discarded and the organic phase was washed with 150 ml 5% Na2CO3 four times. The aqueous washings were canbined and acidified with HCl, extracted with methylene chloride, dried and concentrated to yield 25.3 g of crude product. The crude prcduct was dissolved in ether and stirred with 250 ml of 5% copper (II) acetate. The resulting copper salt was filtered, washed with ether and stirred with 6N hydrochloric acid to destroy the salt. The extract was washed with ether to yield 22.15 grans of the desired product m.p. 138-140 C. (77.7% yield). The structure was confirmed by instrunental analysis. The following is a table of certain selected compounds that are preparable according to the procedure described hereto. Compound numbers are assigned to each compound and are used throughout the remainder of the application. TABLE I EMI6.1 Compound ND30 Number R R1 R2 R4 R5 or m.p. C 1 CH3 CH3 Cl H H H 1.5613 2 CH3 CH3 Cl H 4-Cl H 1.5655 3 CH3 CH3 Cl H H 5-Cl 103-108 4* H H Cl H 4-Cl H 138-140 5 CH3 CH3 2 Br H H H 6 CH3 CH3 2-Cl H H 5-C1 74-77 7 H H Cl H H 5-Cl 104-107 8 H H Br H H H 93-96 9 H H Cl H H H 79-87 10 H H I H H H 66-70 11 H H Cl H 4-NO2 H 118-122 EMI7.1 <tb> <SEP> TABLE <SEP> I <tb> <SEP> (continued) <tb> Ccxllpoti <SEP> ND30 <tb> Number <SEP> R <SEP> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> R5 <SEP> orm.p. <SEP> C <tb> <SEP> 12 <SEP> H <SEP> H <SEP> C1 <SEP> H <SEP> H <SEP> 6-C1 <SEP> 143-148 <tb> <SEP> 13 <SEP> H <SEP> H <SEP> C1 <SEP> H <SEP> H <SEP> 5-Br <SEP> 109-115 <tb> <SEP> 14 <SEP> H <SEP> H <SEP> I <SEP> 3-I <SEP> H <SEP> 5-I <SEP> 164-167 <tb> <SEP> 15 <SEP> H <SEP> H <SEP> C1 <SEP> H <SEP> H <SEP> 5-CH3 <SEP> 60-65 <tb> <SEP> 16 <SEP> H <SEP> H <SEP> Cl <SEP> H <SEP> 4-CH30 <SEP> H <SEP> 79-86 <tb> <SEP> 17 <SEP> H <SEP> H <SEP> C1 <SEP> H <SEP> 4-CH3 <SEP> H <SEP> 60-63 <tb> <SEP> 18 <SEP> H <SEP> H <SEP> C1 <SEP> 3-Cl <SEP> H <SEP> 6-C1 <tb> <SEP> 19 <SEP> H <SEP> H <SEP> C1 <SEP> H <SEP> H <SEP> 5-CH30 <SEP> 77-80 <tb> <SEP> 20 <SEP> H <SEP> H <SEP> C1 <SEP> 3-Cl <SEP> H <SEP> H <SEP> 80-90 <tb> <SEP> 21 <SEP> H <SEP> H <SEP> C1 <SEP> H <SEP> H <SEP> 5-CF3 <SEP> 74-75 <tb> <SEP> 22 <SEP> H <SEP> H <SEP> C1 <SEP> H <SEP> H <SEP> 5-NO2 <SEP> 140-143 <tb> <SEP> 23 <SEP> H <SEP> H <SEP> C1 <SEP> 3-C1 <SEP> 4-C1 <SEP> H <SEP> 152-154 <tb> <SEP> 24 <SEP> H <SEP> H <SEP> C1 <SEP> 3-C1 <SEP> 4-CH30 <SEP> H <SEP> 169-170 <tb> <SEP> 25 <SEP> H <SEP> H <SEP> C1 <SEP> H <SEP> 4-Br <SEP> H <SEP> 104-107 <tb> <SEP> 26 <SEP> CH3 <SEP> CH3 <SEP> CH30 <SEP> H <SEP> H <SEP> H <SEP> 104-108 <tb> <SEP> 27 <SEP> H <SEP> H <SEP> Cl <SEP> H <SEP> (a) <SEP> H <tb> <SEP> 28 <SEP> H <SEP> H <SEP> Br <SEP> H <SEP> H <SEP> (b) <tb> <SEP> 29 <SEP> H <SEP> H <SEP> CH30 <SEP> 3-CH30 <SEP> H <SEP> H <SEP> 75-79 <tb> <SEP> 30 <SEP> H <SEP> H <SEP> CH30 <SEP> H <SEP> H <SEP> 5-CH30 <SEP> 89-92 <tb> <SEP> 31 <SEP> H <SEP> H <SEP> Br <SEP> H <SEP> 4-CH30 <SEP> 5-CH30 <SEP> 92-96 <tb> <SEP> 32 <SEP> H <SEP> H <SEP> Br <SEP> H <SEP> (4)--OCH(5) <SEP> 63-68 <tb> <SEP> 33 <SEP> CH3 <SEP> CH3 <SEP> C1 <SEP> 3-C1 <SEP> 4-C1 <SEP> H <SEP> 86-89 <tb> <SEP> 34 <SEP> H <SEP> H <SEP> C1 <SEP> 3-Cl <SEP> H <SEP> 5-C1 <tb> <SEP> 35 <SEP> CH3 <SEP> CH3 <SEP> C1 <SEP> 3-C1 <SEP> H <SEP> 5-C1 <SEP> 105109 <tb> <SEP> 36 <SEP> CH3 <SEP> CH3 <SEP> C1 <SEP> 3-C1 <SEP> 4-C1 <SEP> 5-C1 <SEP> 137-139 <tb> <SEP> 37 <SEP> H <SEP> H <SEP> Cl <SEP> 3-C1 <SEP> 4-C1. <SEP> 5-C1 <SEP> 106-110 <tb> <SEP> 38 <SEP> H <SEP> H <SEP> C1 <SEP> H <SEP> 4-Cl <SEP> 5-C1 <SEP> 108-111 <tb> <SEP> 0 <tb> <SEP> It <tb> <SEP> 39 <SEP> CH(CH3)20-C- <SEP> H <SEP> C1 <SEP> H <SEP> 4-81 <SEP> H <tb> <SEP> 0 <tb> <SEP> 40 <SEP> CHO- <SEP> H <SEP> C1 <SEP> H <SEP> 4-Cl <SEP> H <tb> <SEP> 41 <SEP> CH(CH3)2 <SEP> H <SEP> C1 <SEP> H <SEP> 4-C1 <SEP> H <tb> <SEP> 42 <SEP> CH(CH3)2 <SEP> H <SEP> Cl <SEP> 3-C1 <SEP> 4-C1 <SEP> H <tb> TABLE I (continued) Compound ND 30 Number R RÚ Rê R R4 R5 or m.p. C 43 H H Cl H 4-F H 44 sodium salt of Compound No. 23 85-94 45 isopropylanine salt of Compound No. 23 160-165 46 triethylanine salt of Compound No. 23 82-85 47 potassiun salt of Compound No. 23 107-106 48 triethanol ammonium salt of Compound No. 39 49 sodium salt of Compound No. 43 60-63 50 CH(CH3)2 H Cl 3-OCH3 4-Br H 51 H H Cl H 4-CH3S02- H 52 H CH3 Cl H 4-C1 H 53 i-C4H7 H Cl H 4-C1 H 54 i-C3H5 H Cl 3-OCH3 H H 55 CH3 CH3 Cl H 4-CH3SO2- H 56 CH3 CH3 Cl 3-CH3 4-C1 H 57 H H Cl 3-CH3 4-C1 H 58 H H Cl H 4-C2H5SO2- H 98-100 59 H H Cl 3-C1 4-C2H5SO2- H 98-109 60 H H Cl H 4-C3H7S02- H semi-solid 61 H H Cl 3-OCH3 4-CH3S02- H 48-59 62 CH3 CH3 Cl H 4-n-C3H7So2- H semi-solid 63 H H Cl 3-C1 4-n-C3H7So2- H 145-148.5 64 H H Cl 3-C2H5SO2- H oil 65 CH3 CH3 Cl H 4-C2H5SO2- H 103-108 66 CH3 CH3 Cl 4-C2H5SO2- H 108-111 67 i-C3H7 H Cl H 4-C2H5SO2- H brown gun 68 H H Cl 3-C1 4-CH3SO2- H 145-154 69 i-C3H7 H Cl 3-C1 4-CH3S02- H 70 H H Br H 4-CH3SO2 H brown gum 71 H H Cl H 4-i-C3H7SO2- H 72 H H Cl H 4-C3S- H 70-77 73 H H Cl 3-Cl 4-CH3S- H 74 CH3 CH3 Cl 3-C1 4-C2H5SO2- H 120-123 MBIE I (continued) Compound ND 30 Number R RÚ Rê R R4 R5 or m.p. C 75 H H C1 H 4-n-C4HsS02- H 76 CH3 CH3 Cl H 4nrC4HgSOr H 77 H H Cl 3-OC2H5- 4-CH3SO2- H semi-solid 78 H H C1 3-OCH3 4-n-C3H7SO2- H golden gun 79 CH3 CH3 C1 H 4-i-C3H7SO2- H 125-128 * = Prepared in exanple. EMI9.1 and EMI9.2 Herbicidal Screening Tests As previously mentioned, the herein described compounds produced in the above-descrbed manner are phytotoxic compounds 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. On the day preceding treatment, seeds of eight different weed species are planted in loamy 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) (Ipanoea lacunosa), velvetleaf (VL) (Abutilon theophrasti), Indian mustard (MD) (Brassica juncea), redroot pigweed (PW) (Amaranthus retroflexus) or curly dock (CD) (Rumex crispus), and yellow nutsedge (YNG) (Cyperus esculentus). Ample seeds are planted to give about 20 to 40 seedlings per row, after energence, depending upon the size of the plants. Using an analytical balance, 600 milligrans (mg) of the canpourd 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-mouth 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 Ib/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 same age. The injury rating fran 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 fl Pre-Emergence Herbicidal Activity Application Rate - 4.48 kWba Ompd. No. FT WG WO AMG VL MD PW CD YNG 1 100 90 20 40 65 50 35 80 2 80 90 0 30 80 90 20 90 3 0 0 0 40 40 40 0 0 4 100 100 50 35 100 100 90 95 5 100 95 65 35 90 85 50 95 6 50 25 0 25 100 100 35 80 7 80 90 10 60 100 100 100 80 8 95 95 45 40 100 80 95 95 9 95 100 55 30 100 90 100 95 10 100 100 60 20 85 100 100 95 11 85 100 30 40 100 100 100 95 12 85 85 90 75 80 95 90 90 13 85 75 10 10 85 65 95 90 14 40 10 80 0 65 40 65 100 15 40 60 -20 30 100 30 75 95 16 80 80 20 55 75 90 40 95 oBIE II (Continued) Cnpd. No. FT W; m AMG VL MD PW CD YNG 17 20 - 10 25 100 95 85 90 18 65 - 30 70 100 100 85 90 19 45 60 0 30 40 0 20 60 20 30 85 20 40 95 85 40 45 21 80 100 0 80 100 100 95 95 22 20 10 0 20 75 30 45 10 23 45 95 10 0 100 85 100 95 24 - 100 0 25 70 90 - 100 25 - 100 25 80 100 100 - 100 26 40 15 0 0 0 10 0 30 27 40 80 10 20 60 50 30 75 28 65 75 0 65 100 95 75 55 29 100 95 55 10 80 75 85 95 30 20 20 20 10 40 40 50 20 31 75 95 20 20 100 95 75 10 32 90 85 20 0 100 85 75 30 33 80 70 0 40 20 40 90 80 34 60 40 0 20 95 100 100 60 35 0 10 0 0 10 20 20 10 36 0 0 0 20 100 100 100 0 37 40 0 0 20 100 60 90 38 10 40 0 20 90 80 20 20 39 80 10 0 0 0 0 0 90 40 60 0 0 0 0 0 0 90 41 100 100 85 40 95 100 100 100 42 60 100 25 0 0 0 0 25 43 100 100 45 40 80 90 90 100 44 90 100 0 60 100 100 100 95 45 100 100 0 60 100 100 100 100 46 20 60 0 100 100 100 100 20 47 60 70 20 100 100 100 100 60 48 60 0 0 0 0 0 0 40 TABIE II (continued) Cnpd. No. FT WG WO AMG VL MD PW CD YNG 49 100 100 50 10 60 20 90 100 50 100 100 80 10 60 60 90 100 51 100 100 90 100 100 100 85 100 52 100 100 60 10 100 100 60 100 53 0 20 0 0 20 20 0 10 54 10 45 10 0 0 0 0 40 55 90 100 60 100 100 100 90 100 56 100 100 80 10 60 60 90 100 57 100 100 90 100 100 100 85 100 58 90 95 0 20 20 40 40 100 59 95 100 85 75 100 100 90 98 60 95 100 50 50 100 100 90 98 61 100 100 75 100 100 100 95 95 62 100 100 95 75 100 100 100 80 63 100 100 40 65 100 100 100 95 64 100 100 98 100 100 100 100 90 65 100 100 80 100 100 100 100 90 66 100 100 75 100 100 100 100 98 73 100 100 60 80 100 100 75 90 74 100 100 70 80 100 100 80 100 75 70 100 0 50 100 100 100 80 76 40 90 25 10 100 100 100 10 77 100 100 90 100 100 100 85 78 100 100 80 100 100 100 90 - - Species did not germinate for some reason. A blank indicates that the wed was not tested. Postnergence Bbicide nest: This test is conducted in an identical manner to the testing procedure for the pre-nergenoe 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-emergence herbicide test are reported in Table III. TABLE III post-Emergence Herbicidal Activity Application Rate - 4.48 Wha Cmpd. No. FT WG WO AMG VL MD PW CD YNG 1 60 70 20 40 60 60 35 60 2 30 70 0 50 90 85 30 80 3 0 30 0 70 100 90 55 70 4 95 98 20 98 100 100 30 95 5 80 80 75 50 60 80 0 95 6 40 40 10 60 100 100 75 65 7 60 75 40 60 100 75 100 75 8 85 80 75 70 95 80 90 90 9 85 80 75 70 95 80 90 90 10 95 85 90 60 95 95 80 95 11 50 80 35 55 100 100 95 80 12 45 75 50 55 75 60 50 80 13 30 60 20 60 80 50 60 70 14 20 10 20 50 45 40 40 0 15 65 95 0 65 95 30 100 80 16 65 80 20 85 85 30 30 80 17 75 80 30 70 100 100 85 90 18 100 95 10 100 100 100 100 90 19 60 80 40 70 100 75 80 90 20 65 80 10 85 95 95 100 70 21 30 55 0 80 100 80 65 80 22 0 30 0 20 45 0 30 20 23 85 90 40 85 100 95 100 90 24 0 80 0 70 90 74 - 100 25 100 100 75 90 100 100 - 100 26 45 30 0 40 70 65 0 45 27 75 80 30 65 50 45 85 85 28 75 60 60 75 100 70 80 25 29 85 85 85 75 85 65 65 85 TABLE III (continued) Cmpd. No. FT WG WO AMG VL MD PW CD YNG 30 75 50 20 10 0 0 20 40 31 60 60 20 40 40 70 100 40 32 60 25 20 40 90 65 20 40 33 10 0 0 10 10 10 100 40 34 10 10 0 5 50 30 80 0 35 0 0 0 10 60 30 40 0 36 0 0 0 20 20 20 0 0 37 0 0 0 30 40 20 80 0 38 10 10 10 20 10 20 20 10 39 40 40 20 0 0 0 5 80 40 90 70 40 20 60 80 20 65 41 60 85 85 20 40 60 100 100 42 60 50 40 70 20 40 60 60 43 100 80 30 60 100 100 80 100 44 80 85 0 60 90 90 100 80 45 90 90 10 100 100 100 100 90 46 80 100 0 60 100 100 100 100 47 100 100 0 60 100 100 100 100 48 40 40 20 10 10 10 90 40 49 40 40 40 80 100 100 60 60 50 80 60 60 50 50 60 80 70 51 80 80 95 100 100 100 100 90 52 60 60 20 20 40 40 90 60 53 10 20 20 0 0 0 0 20 54 20 40 20 5 0 0 0 40 55 40 40 40 60 60 60 80 90 56 80 60 60 50 50 60 80 70 57 80 80 80 95 100 100 100 90 58 60 70 10 70 10 10 20 80 59 100 100 90 100 - 100 100 50 60 100 100 100 100 - 100 100 70 61 90 85 90 85 - 100 100 80 62 100 85 100 75 100 100 100 35 TABLE III (continued) Cmnd. No. FT WG WO AMG VL MD PW CD YNG 63 70 80 20 100 100 100 35 40 64 75 75 90 70 90 70 40 40 65 100 70 100 55 90 95 100 40 66 100 75 100 90 95 95 100 20 73 100 100 95 100 100 100 55 30 74 100 95 75 100 100 100 85 40 75 100 100 30 95 80 100 80 40 76 80 80 75 75 100 95 95 25 77 80 80 80 90 90 80 90 80 78 80 85 75 85 80 95 100 50 Pre-Emergence Multi-Weed Herbicide Test Several compounds were evaluated at an application rate of 2 acre (2.24 kg/ha) for Fre-emergence activity against a larger number of weed sFeices. The process was generally similar to the pre-emergence herbicide test described above except that only 300 milligrans of test comound were weighed out and the application rate was 40 gallons Fer acre. Redroot pigweed (PW) ard curly dock (CD) were eliminated in this test and the following weed species were added: Grasses : Downybrome Bromus tectorum (DB) annual ryegrass Lolium multiforum (ARG) rox-orange sorghum Sorghum bicolor (SNC) hemp sesbania Sesbania exaltata (SESB) nightsaade Solanum sp. (SP) cocklebur Xattiium sp. (CB) The results of the test are shown in Table IV. TABLE IV Pre-Emergence Milti-weed Herbicide Test Cmpd. No. DB FT ARG WG SHC WO BSG AMG SESB VL SP MD YNS CB 67 20 90 25 98 80 60 90 45 90 45 20 85 85 15 68 65 98 98 100 100 60 95 100 100 100 80 100 95 100 69 65 100 70 100 100 65 95 100 95 70 65 100 90 70 98 100 100 100 100 90 98 90 100 90 60 100 95 80 71 60 20 100 100 100 80 95 35 40 100 20 90 100 40 72 100 100 100 100 100 100 100 100 90 100 60 100 100 20 The compounds of the present invention are useful as herbicides, especially as pre-emergence 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 admixture, in herbicidally effective amounts, with the adjutants ard 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 compounds may be formulated as granules of relatively large particle size, as wettable powders, as emulsifi- able concentrates, as popery dusts, as solutions or as any of several other known types of formulations, depending upon the desired mode of application. Preferred formulations for pre-energence herbicidal applied tions 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 anount depends upon the nature of the seeds or plants to be controlled and the rate of application varies fran about 0.05 to approximately 25 pounds per acre, preferably fran about 0.1 to about 10 pounds per acre. Wettable powders are in the form of finely divided Farticles 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 pokers include fuller's earth, kaolin clays, silicas and other readily vet organic or inorganic diluents. Wettable Folders 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 hanogeneous 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 aromatic 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 relatively coarse particles, are usually applied without dilution to the area in which suppression of vegetation is desired. Typical carriers for granular 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 toxicant. Granular formulations normally are prepared to contain 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. Typical wetting, dispersing or enulsifying agents used in agricultural formulations include, for example, the alkyl and alkyl yl sulfonates and sulfates and their sodium salts; polyhydric alcohols; and other types of surface-active agents, many of which are available in can 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 ard other organic and inorganic solids which act as dispersants and carriers for the toxicant, are useful formulations for soil-inivorporatirs application. Pastes, which are homogeneous suspensions of a finely divided solid toxicant in a liquid carrier such as water or oil, are employad for specific purposes. The formulations normally contain about 5% to about 95% of active ingredient by weight, and may also contain small anoints of a wetting, dispersing or emulsifying agent to facilitate dispersion. Eór 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 ard 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 Ereons, may also be used. The phytotoxic compositions of this invention are applied to the plants in the conventional manner. Thus, the dust and liquid compositions can be applied to the plant by the use of powebdusters, boom and hand sprayers and spray dusters. The compositions 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 exanple, the dust and liquid compositions are applied to the soil according to conventional methods and are distributed in the soil to a depth of at least 1/2 inch below 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 spraying or sprinkling the surface of the soil. The phytotoxic composi- tions 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 liauid 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. The Eh;ytotoxic compositions of this invention can also contain other additanents, for example, fertilizers ard other herbicides, pesticides and the like, used as adjutant or in combination with any of the above-described adjuvants. Other phiytotoxic compounds useful in combina- tion with the above-described compounds include, for example, 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) acetanil ide; ; 2,4-dichlorophenaxyacetic acids, 2,4,5- tr ichlorophen- oxyacetic acid, 2-methyl-4-chlorophenoxyacetic acid and the salts, esters and amides 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)-l,l-dimethylurea and 3-( p-chlorophenyl)-l ,l-dimethylurea; and acetanides such as N,N-diallyl &alpha;-chloroacetamide, and the like; benzoic acids such as 3-amino-2,5-di- chlorobenzoic acid ; thiocarbamates such as S-(1,1-dimethylbenzyl)-piper de-1 -carbothiaote, 3-(4-chlorophenyl)-methyl diethylcarbothioate, ethyl1-hexahydro-1,4-azepine-1-carbothicate, S-ethyl-hexahydro-1H-azepine-1carbothioate, S-propyl N,N-dipropylthiocarbamate, S-ethyl N,N-dipropylthiocarbanate, S-ethyl cyclohexylethylthioc art,anate, S-ethyl hexahydro-lHazopine-1-carbothioate and the like; anilines such as 4-(methylsulfonyl)2,6-dinitro-N,N-substituted aniline, 4-trifluoromethyl-2,6-dinitro-N,N-din-propyl aniline, 4-trifluoromethyl0-2,6-dinitro-N-ethyl-N-butyl aniline, 2-[4-(2,4-dichlorophenoxy) phenoxypropanoic acid, 2-[1-(ethoxyimino)butyl]-5-[2-ethylthio) propyl]-3-hydroxy-2-cyclohexene-1-one, (#)-butyl-2- [4-[(5-trifluoromethyl)-2-pyridinyl) oxy] phenoxy] propenate, sodium 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate, 3-isopropyl-1H2,1,3-benzothiadiazine-4(3H)-one-2,2-dioxide, and 4-amino-6-tert-butyl-3 (methlthio)-s-triazin-5(4H)-one or (4-amino-6-(1,1-dimethylethyl)-3 (methylthio)-1,2,4-triazin-5 (4H )-one) and S- (O,iisopropyl )-benzene sulfonanide. rtilizers useful in canbination with the active ingredients include, for exanple, amonium nitrate, urea and superphosphate. Other useful additaments include materials in which plant organisns take root and grow such as compost, manure, humus, sand, and the like.

Claims: WE CLAIM: 1. A compound having the structural formula EMI20.1 wherein R and R1 are hydrogen, C1-C4 alkyl, RPCC(O)-, where Ra is C1-C4 alkyl; R2 is chlorine, bromine, iodine or C1=C4 alkoxy; and R3, R4 and R5 independently are hydrogen or an aliphatic group, and their salts with the proviso that compounds having the structural formula EMI20.2 wherein R and R1 are hydrogen or C1-C4 alkyl; R2 is chlorine, bromine, or iodine; R3 is hydrogen, iodine or chlorine; and R4 is hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, nitro, or trifluoranethyl are excluded. 2. The compounds of Claim 1 wherein R and R1 are hydrogen or C1-C4 alkyl; R2 is chlorine, bromine, iodine or C1-C4 alkoxy; R3, R4 and R5 independently are hydrogen, halogen, C1 4 alkyl, C1 -C4 alkoxy, CCF3, cyano, nitro, C1-C4 haloalkyl, RbSOn wherein Rb is C1-C4 alkyl; C1-C4 haloalkyl, phenyl, benzyl, dry wherein Rd and Re independently are hydrogen and C1-C4 alkyl; and n is the integer 0, 1 or 2; RCC(O)NH- wherein PC is C1-C4 alkyl; RfC(O)- wherein Rf is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy; or -NRgRh wherein Rg and Rh independently are hydrogen or C1-C4 alkyl and their salts. 3. The compounds of Claim 1 wherein R and R1 are hydrogen or methyl; R2 is chlorine or methoxy; R3 is hydrogen, chlorine, dimethylanino or methoxy; R4 is hydrogen, chlorine, nitro, S02CH3, S02N(CH3)2 or CF3; and R5 is hydrogen and their salts. 4. The canpounds of Claim 3 wherein R3 is substituted at the 3-position, R4 is substituted at the 4-position and R5 is substituted at the 5- or 6-position and their salts. 5. The compounds of Claim 3 wherein R and R1 are hydrogen; R2 is chlorine or methoxy R3 is hydrogen, 3-chlorine, 4-methoxy or 3-dimethylamino and R4 is 4 chlorine, 4-CH3S02- or 4-CF3S02; and R5 is hydrogen and their salts. 6. The compounds of Claim 2 wherein R2 is chlorine and their salts. 7. The canpound of Claim 1 wherein R is methyl, R1 is methyl, R2 is chlorine, R3 is hydrogen, R4 is hydrogen, and R5 is 6-chlorine and its salts. 8. The compound of Claim 1 wherein R is hydrogen, R1 is hydro gen, R2 is is chlorine, R3 is hydrogen, R4 is hydrogen, R5 is 6-chlorine and its salts. 9. The compound of Claim 1 wherein R is hydrogen, R1 is hydro gen, R2 is chlorine, R3 is hydrogen, R4 is 4-chlorine and R5 is hydrogen and its salts. 10. The compound of Claim 1 wherein R is hydrogen, R1 is hydro gen, R2 is chlorine, R3 is 3-chlorine and R4 is hydrogen and R5 is 6-chlorine and its salts. 11. The compound of Claim 1 wherein R is hydrogen, R1 is hydro gen, R2 is chlorine, R3 is hydrogen, R4 is hydrogen and R5 is 5-trifluorb methyl and its salts. 12. The compound of Claim 1 wherein R is hydrogen, R1 is hydro gen, P2 is chlorine, R3 is 3-chlorine, R4 is 4-chlorine and R5 is hydrogen and its salts. 13. The compound of Claim 1 wherein R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chlorine, R4 is 4methoxy and R5 is hydrogen and its salts. 14. The compound of Claim 1 wherein R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4-bromine and R5 is hydrogen and its salts. 15. The compound of Claim 1 wherein R is hydrogen, R1 is hydrogen, R2 is methoxy, R3 is 3=methoxy, R4 is hydrogen and R5 is hydrogen and its salts. 16. The compound of Claim 1 wherein R is isopropyl, R1 is hydrogen, R2 is chlorine, R3 is hydorgen, R4 is 4-chlorine and R5 is hydrogen and its salts. 17. The compound of Claim 1 wherein R is isopropyl, R1 is hydrogen, R2 is chlorine, R3 is 33, R4 is 4-CH3S02 and R5 is hydrogen and its salts. 18. The compound of Claim 1 wherein R is hydrogen, R1 is hydra gen, R2 is chlorine, R3 is hydrogen, R4 is 4"CH3S02 and R5 is hydrogen and its salts. 19. The sodium, isopropylanine, triethylanine and potassium salts of the compound of Claim 12. 20. The method of controlling undesirable vegetation canprising applying to the area where control is desired, an herbicidally effective amount of a compound having the formula EMI22.1 wherein R and R1 are hydrogen, C14 alkyl, RaCC(O)-, where Ra is C1-C4 alkyl; R2 is chlorine, bromine, iodine or C1-C4 alkoxy; and R3, R4 and R5 independently are hydrogen or an aliphatic group with the proviso that compounds having the structural formula EMI23.1 wherein R and RÚ are hydrogen or C1-C4 alkyl; R2 is chlorine, bromine, or iodine; R3 is hydrogen, iodine or chlorine; and R4 is hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, nitro, or trifluoromethyl are excluded. 21. The method of Claim 20 wherein Rand R1 are hydrogen or C1-C4 alkyl; R2 is chlorine, bromine, iodine or C14 alkoxy; R3, R4 and R5 independently are hydrogen, halogen, C1-C4 alkyl, C1-C4 $alkoxy, OCF3 ; cyano, nitro, C1-C4 haloalkyl, RbSOn wherein Rb is C14 alkyl; C1-C4 haloalkyl, phenyl, benzyl, -NRdRe wherein Rd and Re independently are hydrogen and C1-C4 alkyl; and n is the integer 0j 1 or 2; RCC(O)NH- wherein Rc is C1-C4 alkyl; RfC(O)- wherein Rf is hydrogen, C1-C4 alkyl, C2-C4 haloalkyl, C14 alkoxy; or -NHrRh wherein Rg and Rh independently are hydrogen or C1-C4 alkyl and their salts. 22. The method of Claim 20 wherein R and R1 are hydrogen or methyl; R2 is chlorine or methoxy; R3 is hydrogen, chlorine or methoxy; R4 is hydrogen, chlorine, nitro, So2CH3, S02N(CH3)2 or CF3; and R5 is hydrogen and their salts. 23. The method of Claim 22 wherein R3 is substituted at the 3-position, R4 is substituted at the 4-position and R5 is substituted at the 5- or 6-position and their salts. 24. The method of Claim 22 wherein R and R1 are hydrogen; R2 is chlorine or methoxy; R3 is hydrogen, 3-chlorine, 3-methoxy or 3-dinnethylanino; R4 is 4-chlorine, 4-CH2SO2, or 4-CF3SO2; and R5 is hydrogen and their salts. 25. The method of Claim 24 wherein R2 is chlorine and their salts. 26. The method of Claim 20 wherein R is methyl, R1 is methyl, R2 is chlorine, R3 is hydrogen, R4 is hydrogen, and R5 is 6-chlorine and its salts. 27. The method of Claim 20 wherein R is hydrogen, R1 is hydrogen, R2 is is chlorine, R3 is hydrogen, R4 is hydrogen, R5 is 6-chlorine and its salts. 28. The method of Claim 20 wherein R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4-chlorine and R5 is hydrogen and its salts. 29. The method of Claim 20 wherein R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chlorine and R4 is hydrogen and R5 is 6-chlorine and its salts. 30. The method of Claim 20 wherein R is hydrogen, R1 is hydrogen, Rê is chlorine, R3 is hydrogen, R4 is hydrogen and R5 is 5-trifluaro- methyl ard its salts. 31. The method of Claim 20 wherein R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chlorine, R4 is 4-chlorine and R5 is hydrogen and its salts. 32. The method of Claim 20 wherein R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chlorine, R4 is 4-methoxy and R5 is hydrogen and its salts. 33. The method of Claim 20 wherein R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4-bromine and R5 is hydrogen and its salts. 34. The method of Claim 20 wherein R is hydrogen, R1 is hydrogen, R2 is methoxy, R3 is 3-methoxy, R4 is hydrogen and R5 is hydrogen and its salts. 35. The method of Claim 20 wherein R is isopropyl, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4 chlorine and R5 is hydrogen and its salts. 36. The method of Claim 20 wherein R is hydrogen, R1 is hydrogen, Rê is chlorine, R3 is 3-CH3O, R4 is 4 < H3S02 chlorine and R5 is hydrogen and its salts. 37. The method of Claim 20 wherein R is hydrogen, R1 is hydrogen, Rê is chlorine, R3 is hydrogen, R4 is 4-CH3SO2 and R5 is hydrogen and its salts. 38. The sodium, isopropylanine, triethylanine and potassium salts of the method of Claim 31. Claims for Austria 1. Process for preparing compounds having the structural formula EMI26.1 wherein R and RÚ are hydrogen, C1-C4 alkyl, RaOC(O)-, where Ra 15 C1-C4 alkyl ; @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@C1-C4 alkoxy ; and R3, R4 and R5 independently are hydrogen or an aliphatic group, and their salts with the provis@ that compounds having the structural rormula EMI26.2 wherein R and RÚ are hydrogen or C1-C4 alkyl; R2 is chlorine, branine, or iodine; R3 is hydrogen, iodine or chlorine; and R4 is hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, nitro, or trifluoromethyl are excluded. comprising reacting a substituted dione of the qeneral formula II EMI26.3 with a substituted benzoyl cyanide of the general formula III EMI26.4 and working up the reaction product by conventional techniques. 2. The process of Claim 1 wherein R and R1 are hydrogen or C1-C4 alkyl; R2 is chlorine, branine, iodine or C1-C4 alkoxy; R3, R4 and R5 inde- pendently re hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, OCF3, cyano, nitro, C1-C4 haloalkyl, RbSOn wherein Rb is C1-C4 alkyl ; C1-C4 haloalkyl, phenyl, benzyl, -NRdRe wherein Rd and Re independently are hydrogen and C1-C4 alkyl; and n is the integer 0, 1 or 2; RcC(O)NH0- wherein Rc is C14 alkyl; RfC(O)- wherein i is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy; or -NRgRh wherein Rg and .$ independently are hydrogen or C1-C4 alkyl and their salts. 3. The prccess of Claim 1 wherein R and RÚ are hydrogen or methyl; R2 is chlorine or methoxy; R3 is hydrogen, chlorine, dimethylanino or metnoy; R4 is hydrogen, chlorine, nitro, SO2CH3, So2N(CH3)2 or CF3 ; and R5 is hydrogen and their salts. 4. The process of Claim 3 wherein R3 is substituted at the 3-position, R4 is substituted at the 4-position and R5 is substituted at the 5- or 6-position and their salts. 5. The process of Claim 3 wherein R and R1 are hydrogen; R2 is chlorine or methoxy; R3 is hydrogen, 3-chlorine, 4-methoxy or 3-dimethylastino and R4 is 4-chlorine, 4-CH3SO2- or 4-CF3SO2 ; and R5 is hydrogen and their salts. 6. The process of Claim 2 wherein R2 is chlorine and their salts. 7. The process of Claim 1 wherein R is methyl, R1 is methyl, R2 is chlorine, R3 is hydrogen, R4 is hydrogen, and R5 is 6-chlorine and its Salts. 8. The process of Claim 1 wherein R is hydrogen, R1 is hydrogen, R2 is is chlorine, R3 is hydrogen, R4 is hydrogen, R5 is 6-chlorine and its salts. 9. The process of Claim 1 wherein R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4-chlorine and R5 is hydrogen and its salts. 10. The process of Claim 1 wherein R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chlorine and R4 is hydrogen and R5 is 6-chlorine and its salts. 11. Theprocess of Claim 1 wherein R is hydrogen, R1 is hydro- gen, R2 is chlorine, R3 is hydrogen, R4 is hydrogen and R5 is 5-trifluoro- methyl and its salts. 12. Theprocess of Claim 1 wherein R is hydrogen, R1 is hydro- gen, R2 is chlorine, R3 is 3=chlorine, R4 is 4-chlorine and R5 is hydrogen and its salts. 13. The process ' of Claim wherein R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chlorine, R4 is 4-methoxy and R5 is hydrogen ard its salts. 14. The process of Claim I wherein R is hydrogen, R1 is hydro- aen, R2 is chlorine, R3 is hydrogen, R4 is 4-bromine and R5 is hydrogen and its salts. 15. The process of Claim 1 wherein R is hydrogen, R1 is hydro- gen, R2 is methoxy, R3 is 3-metboxy, R4 is hydrogen and R5 is hydrogen and its salts. 16. The process-of Claim 1 wherein R is isopropyl, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4-chlorine and R5 is hydrogen and its salts. 17. The process of Claim 1 wherein R is isopropyl, R1 is hydro- gen, R2 is chlorine, R3 is 3-CH3, R4 is 4-CH3So2 and R5 is hydrogen and its salts. 18. The. processof Claim 1 wherein R is hydrogen, RÚ is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4-CH3SO2 and R5 is hydrogen and its salts. 19. The process of claim 12 comprising preparing the sodium, isopropylamine, triethylamine and potassium salts of the compound of Claim 12. 20. The method of controlling undesirable vegetation canprising applying to the area where control is desired, an herbicidally effective amount of a compound having the formula EMI29.1 wherein R and R1 are hydrogen, C1-C4 alkyl, RaOC(O)-, where Rd is C1-C4 alkyl; R2 is chlorine, branine, iodine or C1-C4 alkoxy; and R3, R4 and R5 independently are hydrogen or an aliphatic group with the proviso that compours having the structural formula EMI30.1 wherein R and RÚ are hydrogen or C1-C4 alkyl; R2 is chlorine, branine, or iodine; R3 is hydrogen, iodine or chlorine; and R4 is hydrogen, halogen, C1-C4 alkyl, C14 alkoxy, nitro, or trifluoromethyl are excluded. 21. The method of Claim 20 wherein R and P1 are hydrogen or C1-C4 alkyl: R2 is chlorine, branine, iodine or C1-C4 alkoxy; R3, R4 and R5 independently are hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, OCF3; cyano, nitro, C1-C4 haloalkyl, RbSOn wherein Rb is C1-C4 alkyl ; C1-C4 haloalkyl, phenyl, benzyl, -NRdRe wherein Rd and Re independently are hydrogen and C1-C4 alkyl; and n is the integer 0, 1 or 2; RcC(O)NH- wherein Rc is C1-C4 alkyl; RfC(O)- wherein Rf is hydrogen, C1-C4 alkyl, C2-C4 haloalkyl, C14 alkoxy; or ÇRh wherein Fa and Rh independently are hydrogen or C1-C4 alkyl and their salts. 22. The method of Claim 20 wherein R and RÚ are hydrogen or methyl; R2 is chlorine or methoxy; R3 is hydrogen, chlorine or methoxy; R4 is hydrogen, chlorine, nitro, So2CH3, SO2N(CH3)2 or CF3 ; and R5 is hydrogen and their salts. 23. The method of Claim 22 wherein R3 is substituted at the 3-position, R4 is substituted at the 4-position and R5 is substituted at the 5- or 6-position and their salts. 24. The method of Claim 22 wherein R and RÚ are hydrogen; R2 is chlorine or methoxy; R3 is hydrogen, 3-chlorine, 3-methoxy or 3-dimethylamino ; R4 is 4-chlorine, 4-CH2SO2, or 4-CF3SO2 ; and R5 is hydrogen and their salts. 25. The method of Claim 24 wherein R2 is chlorine and their salts. 26. The method of Claim 20 wherein R is methyl, R1 is methyl, R2 is chlorine, R3 is hydrogen, R4 is hydrogen, and R5 is 6-chlorine and its salts. 27. The method of Claim 20 wherein R is hydrogen, R1 is hydro- gen, R2 is is chlorine, R3 is hydrogen, R4 is hydrogen, R5 is 6-chlorine and its salts. 28. The method of Claim 20 wherein R is hydrogen, R1 is hydrogen, Rê is chlorine, R is hydrogen, R4 is 4-chlorine and R5 is hydrogen and its salts. 29. The method of Claim 20 wherein R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-chlorine and R4 is hydrogen and R5 is 6-chlorine and its salts. 30. The method of Claim 20 wherein R is hydrogen, RÚ is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is hydrogen and R5 is 5-trifluoro- methyl and its salts. 31. The method of Claim 20 wherein R is hydrogen, R1 is hydro- gen, Rê is chlorine, R3 is 3=chlorine, R4 is 4-chlorine and R5 is hydrogen and its salts. 32. The method of Claim 20 wherein R is hydrogen, R1 is hydro- gen, R2 is chlorine, R3 is 3-chlorine, R4 is 4-methoxy and R5 is hydrogen and its salts. 33. The method of Claim 20 wherein R is hydrogen, R1 is hydro- gen, R2 is chlorine, R3 is hydrogen, R4 is 4-bromine and R5 is hydrogen and its salts. 34. The method of Claim 20 wherein R is hydrogen, R1 is hydro- gen, R2 is methoxy, R3 is 3-mettrxy, R4 is hydrogen and R5 is hydrogen and its salts. 35. The method of Claim 20 wherein R is isopropyl, R1 is hydrogen, R2 is chlorine, R3 is hydrogen, R4 is 4-chlorine and R5 is hydrogen ard its salts. 36. The method of Claim 20 wherein R is hydrogen, R1 is hydrogen, R2 is chlorine, R3 is 3-CH3O, R4 is 4-CH3So2 chlorine and R5 is hydrogen and its salts. 37. The method of Claim 20 wherein R is hydrogen, R1 is hydro- gen, R2 is chlorine, R3 is hydrogen, R4 is 4-CH3SO2 and R5 is hydrogen and its salts. 38. The sodium, isopropylamine, triethylanine and potassium salts of the method of Claim 31.

Inventors: KRAATZ, GARY WAYNE, MICHAELY, WILLIAM JAMES
Applicants: STAUFFER CHEMICAL COMPANY
Application year: 1984
Main classification: C07C49
IPC codes: C07C45, A01N37, C07C317, A01N35, C07C49, C07C62, C07D317, A01N41, A01N43