IL45594A

IL45594A - Bis-substituted succinamides and their use as herbicides

Info

Publication number: IL45594A
Application number: IL45594A
Authority: IL
Original assignee: Stauffer Chemical Co
Priority date: 1973-11-12
Filing date: 1974-09-04
Publication date: 1977-12-30
Also published as: IT1050247B; FR2250740B1; BR7408957D0; DE2451512A1; BR7408957A; IL45594A0; FR2250740A1; CH604505A5; AR209596A1; NL7413652A; JPS5082015A; AU7321174A; GB1441877A

Description

ana ma»»m D'toniD-o'3 D>*»"»atta »opio Bis-substituted suocinamides and their use as herMoidee STAUFPKR CHEMICAL COMPANY C. 43645 This invention relates to certain novel bis-substiTuted succinamides which can be used as herbicides. More specifically, this invention relates to certain ^-halo bis-substituted succinamides, to their preparation and utility of the compounds as herbicides.

The compounds comprising the instant class of compounds correspond to the general formula: in which X is chlorine or bromine; and are hydrogen, alkyl having from 1 to 8 carbon atoms, inclusive, haloalkyl having from 1 to 6 carbon atoms, inclusive, in which halo is fluorine, bromine and chlorine, alkenyl having from 2 to 6 carbon atoms, inclusive, alkynyl having from 2 to 8 carbon atoms, inclusive, or benzyl; and are hydrogen, alkyl having from 1 to 8 carbon atoms, inclusive, alkenyl having from 2 to 6 carbon atoms, inclusive, haloalkenyl having from 2 to 6 carbon atoms, inclusive, in which halo is chlorine or bromine, alkoxy-alkyl having from 2 to 8 carbon atoms, inclusive, alkynyl having from 2 to 6 carbon atoms, cycloalkyl having from 3 to 8 carbon atoms, inclusive, 1-ethynylcyclohexyl , furfuryl, and tetrahydro- furfuryl? or Rx and R2 together may form an alkylene or alkenylene group having from 2 to 8 carbon atoms, inclusive/ the alkylene group being optionally interrupted by an oxygen atom; and R3 and together may form an alkylene or alkenylene group having from 2 to 8 carbon atoms, inclusive, the alkylene grj^p being optionally interrupted by an oxygen atom; and provid7^^" that when R1 , R2 , R3 and R4 are each alkyl, then one of 1 or R2 and one of or R4 is other than methyl; further provided that only one of Rx or R2 is hydrogen and only one of R3 or R4 is hydrogen.

In the above description, the following preferred embodiments are intended for the various substituent groups: Alkyl and haloalkyl preferably includes, unless otherwise provided for, those members which contain from 1 to 6 carbon atoms, inclusive, in both straight chain and branch chain configuations, for example, methyl, trifluoromethyl, ethyl, 2-chloroethyl, n-propyl, isopropyl, n-butyl, sec . -butyl, 1, 1-dimethylbutyl, · amyl, isoamyl, n-hexyl, isohexyl, octyl, isooctyl and the like; alkenyl preferably includes, unless otherwise provided for, those members which contain at least one olefinic double bond and containing from 2 to 6 carbon atoms, inclusive, for example, allyl, methallyl, ethallyl, 1-butenyl, 3-butenyl, 2-methyl-l-but-enyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 2-methyl-l-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and the like; alkenyl and haloalkenyl preferably includes, unless otherwise specified for, those members which contain from 2 to 6 carbon atoms, inclusive, and halo preferably includes chloro or bromo; and alkynyl preferably includes those members which contain from 2 to 8 carbon atoms, inclusive, and at least one acety-lenic unsaturation (triple bond) , for example, 1-propynyl, 2-propynyl (propargyl), 2-butynyl, 3-butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 1-ethynylcyclohexyl and the like; alkoxyalkyl preferably includes those members which contain a total of from 2 to 8 carbon atoms, methoxypropyl, ethoxyethyl, propoxymethyl, propoxypropyl, ^^ o y- butyl and the like; cycloalkyl preferably includes, unless other- wise provided for, those members which contain from 3 to 8 carbon atoms, inclusive, for example, cyclopropyl, cyclobutyl, cyclohexyl, cyclooctyl and the like; the alkylene or alkenylene group formed by and I¾ taken together, and/or by and taken together, preferably includes, unless otherwise provided for, those members which contain from 2 to 6 carbon atoms, inclusive, for example, including those bivalent radicals derived from normal alkanes or alkenes by removal of a hydrogen atom from each of the two terminal carbon atoms of the chain, for example, ethylene, trimethylene, tetramethylene, pentamethylene , hexamethylene , butene-2 and pentene-2; also included are those branch chain members wherein said branched member is a ower alkyl of from 1 to 4 carbon atoms, including such as ethylethylene, 2-methylpentamethylene, 3-methylpenta- methylene and the like, and also alkylene groups interrupted by an oxygen atom such as B-oxydiethylene.

The compounds of this invention have been found to be active herbicides of a general type. Included in the compounds active as herbicides and therefore useful in the method of controlling undesirable vegetation, are those compounds in which R^, R_2» R3 and are each methyl. That is, certain members of the class have been found to be herbicidally effective against a wide range of plant species. A method of controlling undesirable vegetation of the present invention comprises applying an herbicidally effective amount of the above -described compounds to the area or plant locus where control is desired.

An herbicide is used herein to mean a compound \ controls or modifies the growth of plants. By a "growth controlling amount" is meant an amount of compound which causes a modifying effect upon the growth of plants. Such modifying effects include all deviations from natural development, for example, killing, retardation, defoliation, desiccation, regulation, stunting, tillering, stimulation, dwarfing and the like. By "plants", it is meant germinant seeds, emerging seedlings, and established vegetation, including the roots and above-ground portions . ing to the procedure of Freudenberg and Lux, Ber . 61B, pp. 1083-9 at p. 1087 (1928). This reference also discloses the compound bromosuccinic acid-bis-dimethyl amide. According to the procedure by Walden, Ber. 26 , p. 214 (1893) hydroxy succinic acid (malic aci can be reacted with phosphorus pentachloride to prepare the corresponding diacid chlorides.

The bis-substituted succinamides are prepared by several different methods, depending upon the nature of the starting materials and products desired. A preferred method, for example, is the reaction of a desired primary or secondary amine with the -halosuccinoyl chloride in a suitable solvent such as benzene, methylene, chloride, diethyl ether and the like. The use of a solvent is useful to facilitate processing of the reaction and to aid in the agitation by providing adequate volume, as well as solubilizing the reagents. The preferred ratio of amine to acid chloride is 4 to 1.. When the amine is used in excess as preferred the amine acts as an acid acceptor in the reaction. Other amines, 45594/2 at tertiary amines, can be employed as acid acceptors when the ratio of reactant amine to -halosuccinoyl chloride is 2 The addition of reagents in the reaction preferably is such that permits the amine to be added to the <^ -halosuccinoyl chloride in solution. The temperatures for the reaction are best defined between about -30eC. and about +10°C. At these temperatures, the reaction as described hereinabove proceeds rapidly to yield the desired product. In each instance after the reaction is complete, the recovery is carried out by normal work-up procedure such as crystallization, sublimation or distillation.

The compounds of the present invention and their preparation are more particularly illustrated by the following examples. Following the examples is a table of compounds which are prepared according to the procedures described herein.

EXAMPLE I Preparation of Bis-N.N-diallyl- (?(-bromosuccinamide .

A solution of 11.7 g. diallylamine (0.12 mole) in 25 ml. methylene chloride was added dropwise with stirring to 7.0 g. a-bromosuccinoyl chloride (0.03 mole) in 75 ml. methylene chloride at -30° to -25 °C. The reaction mixture was stirred for 1/2 hour after amine addition was complete during which time the temperature rose to 10 °C.

The product was stirred with 100 ml. water, phase separated and then washed with two 100 ml. portions of 5% sulfuric acid solution and one 100 ml. portion of 57» sodium bicarbonate solution. The organic solution was dried over magnesium sulfate, filtered, and the solvent evaporated under vacuum. 30 There.was obtained 8.1 g. of the title compound Nn ∞ 1.5196.

EXAMPLE II Preparation of Ν,Ν' -dibenzyl- -bromosuccinarnide .

A solution of 7.3 g. benzylamine (0.068 mole) and 8.2 N,N-dimethylaniline (0.068 mole) in 25 ml. methylene chloride wa added dropwise with stirring to 8.0 g. oi -bromosuccinoyl chlorid (0.034 mole) in 75 ml. methylene chloride at -30°C. to -25°C. The reaction mixture was washed with 100 ml. water. The insolub solid was removed by filtration and air-dried to give 2.9 g. of the title compound, m.p. 232°C. (dec.). Identification was confirmed by n.m.r. analysis.

EXAMPLE III chlorosuccinoyl dipiperidine) .

A solution of 8.9 g. piperidine (0.104 mole) in 25 ml., methylene chloride was added dropwise with stirring to a solutio of 5.0 g. (0.026 mole) y -chlorosuccinoyl chloride in 75 ml. methylene chloride at -30° to -25°C. The reaction mixture was stirred for 1/2 hour after addition was complete, during which time the temperature rose to 12°C.

The mixture was next stirred with 100 ml. of water, phase separated and the organic layer was washed successively with two 100 ml. portions of dilute hydrochloric acid and two 100 ml. portions of water.

After drying over magnesium sulfate, the solvent was 30 removed in vacuum to leave an oil, 6.5 g., p = 1.5111, identified by n. .r. analysis to be the title compound.

The following is a table of pared according to the aforementioned procedures. Compound numbers have been assigned to them and are used for identification throughout the balance of the specification.

TABLE I COMPOUND o NUMBER X Rl 1 Br H (CH3) 3C H 2 Br CH2-=CHCH2 CH2=CHCH2 3 Br CH3CH2CH2 CH2=CC 1CH2 4 Br 0CH2 H ^CH2 6 C I CH2=C1ICH2 CH2=CC1CH2 CH2=CHCH2 7 Br CH3CIl2CH2 CH3CH2CH2 CH-jC H2 CH2 ; 12 CI CH3 CH≡CCH(CH3) CH3 13 Br C2H5 C2H5 C2H5 14 CI CII3 C2H5 CH3 TABLE I cont nue COM NU 17 CI -(C¾) TABLE I (continue COMPOUND NUMBER X 20 Br CH3CH2- CH2»CHCH2- CH3CH 21 Br CH3- CH2=CHCH2 CH3- 22 Br "^CH2^5" 23 Br n-C H9 CH2=CHCH2 n-C4H9 24 Br CH3CHCH2- CH2 CHCHg- CH CHCH CH3 CH3 25 Br HC=CCH2- HC=CCH2 HC=CCH 26 CI HC≡CCH2- HC=CCH2 HC=CCH 29 Br BrCH2CH2CH2- H BrCH2CH 30 CI BrCH2CH2CH2- H BrCH2CH 31 Br H CH=CC(CH3) H 32 Br -(CH2)6- 33 Br H CH2CH2CH3 H 34 CI H CH2CH=CH2 H 35 Br H HC≡CCH2 Ή TABLE I cont nue COM NU 40 Br H CH0CH=CHCR H 42 Br H CH2=C(CH3)CH2 H 46 Br BrCH2CH2 H BrCH2CH2 48 Br H CH0-CC1CH0 H con nue COMPOUND R, R. NUMBER X 49 Br H CH3 H '50 Br H CH2CH3 H 51 Br H (CH3)2CH H 53 Br H CH^) 2CHCH2 H 54 Br H CH3CH2CH(CH3) H 55 Br H (CH3)2CHCH2CH(CH3) H 58 Br H (CH3CH2)2CH H 59 Br H C1CH-CHCH2 H 60 Br H TABLE I (continued) COMPOUND NUMBER x 61 Br H Cl2C=CHCH2 63 Br H CH2=CH(CH2)2 M Br H HERBICIDAL SCREENING TESTS -& As previously mentioned, the herein described compounds produced in the above-described manner are ph to oxic compounds which are useful and valuable in controlling various plant species Compounds of this invention are tested as herbicides in the following manner.

Pre-emergence Herbicide Screening Test Using an analytical balance¾ 20 mg. of the compound to be tested is weighed out on a piece of glassine weighing paper. The paper and compound are placed in a 30 ml. wide-mouth bottle and 3 ml. of acetone containing 1% Tween 20^ (polyoxyethylene sorbitan monolaurate) is added to dissolve the compound. If the material is not soluble in acetone, another solvent such as water, alcohol or dime hylformamide (DMF) is used instead. When DMF is used, only 0.5 ml. or less is used to dissolve the compound and then another solvent is used to make the volume up to 3 ml. The 3 ml. of solution is sprayed uniformly on the soil contained in a small flat one day after planting weed seeds in the flat of soil. An atomizer is used to apply the spray using compressed air at a pressure of 5 lb/sq. inch. The rate of application is 8 lb/acre and the spray volume is 143 gallons per acre.

On the day preceeding treatment, the flat which is 7 inches long, 5 inches wide and 2.75 inches deep, is filled to a depth of 2 inches with loamy sand soil. Seeds of seven different weed species are planted in individual rows using one species per row across the width of the flat. The seeds are covered with soil so that they are planted at a depth of 0.5 inch. Ample seeds are planted to give about 20 to 50 seedlings per row after "werprnce depending on the size of the plants.

The seeds used are foxtail (Setaria spp.) - FT, water-grass (Echinochloa c rusgalli) - WG, red oat (Avena sativa) - RO, redroot pigweed (Amaranthus retroflexus) - PW, mustard (Brassica juncea) - MD, curly dock (Rumex crispus) - CD, and hairy crabgras (Digitaria sanguinalis) - CG.

After treatment, the flats are placed in the greenhouse at a temperature of 70 to 85°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 from 0 to 100% is recorded for each species as per cent control with 07a representing no injury and 100% representing complete kill.

Post-emergence Herbicide Screening Test Seeds of six plant species, including hairy crabgrass (CG), watergrass (WG) , red oat (RO) , mustard (MD) , curly dock (CD) and Pinto beans (Phaseolus vulgaris) (BN) , are planted in the flats as described above for pre-emergence screening. The flats are placed in the greenhouse at 70 to 85°F. and watered daily with a sprinkler. About 10 to 14 days after planting when the primary leaves of the bean plants are almost fully expanded and the first trifoliate leaves are just starting to form, the plants are sprayed. The spray is prepared by weighing out 20 mg. of the test compound, dissolving it in 5 ml. of acetone containing 1% Tween 20^ (polyoxyethylene sorbitan monolaurate) and then adding 5 ml. of water. The solution is sprayed on the foliage using an atomizer at an air pressure of 5 lb/sq. inch. The spray concentration is 0.2% and the rate is 8 lb/acre. The spray volum is 476 gallons per acre.

The results of these tes ts are shown in Table llg TABLE II HERBICIDAL ACTIVITY - SCREENING RESULTS Per Cent Control at 8 lb /A .

Pre-emergence COMPOUND NUMBER CG FT WG RO PW MD CD 1 90 95 100 30 0 0 0 2 100 100 100 100 100 100 50 3 100 99 100 99 98 80 40 4 80 50 50 40 0 20 20 5 100 100 100 , 99 98 100 30 6 100 99 99 98 100 80 20 7 100 99 100 98 90 90 20 8 99 100 99 100 99 90 80 9 90 90 90 80 20 10 10 10 100 98 99 98 50 80 30 11 100 99 99 95 100 60 20 12 100 100 100 98 100 80 30 15 90 80 70 0 0 0 0 16 80 80 70 40 0 0 0 17 90 90 80 0 0 0 10 18 20 0 0 0 0 0 0 19 95 80 90 70 0 0 0 20 98 98 100 95 . 80 40 20 21 90 90 80 .70 0 0 0 23 100 100 100 95 80 20 30 COMPOUND NUMBER CG FT WG RO PW MD CD 24 98 100 98 90 80 20 20 25 100 100 95 90 70 10 10 31 80 70 70 10 0 0 0 32 100 90 90 70 0 0 10 33 100 100 100 90 70 80 20 34 90 100 95 70 0 0 0 35 100 100 100 80 100 100 70 36 100 100 100 80 20 40 0 37 100 100 100 60 0 0 0 38 100 100 100 98 100 98 90 39 100 99 100 100 50 50 50 40 98 98 100 95 30 40 30 41 100 100 100 95 70 20 20 42 100 100 100 95 0 40 30 43 99 98 100 90 20 50 20 44 100 100 100 40 70 60 20 45 100 100 100 20 80 60 0 47 100 98 100 60 0 10 0 48 100 100 100 70 0 0 0 49 80 80 80 60 0 0 0 50 98 98 100 98 0 20 0 51 98 98 100 100 0 20 10 52 98 100 100 80 0 40 0 53 98 100 100 90 0 50 0 54 98 100 100 100 80 50 20 45594/2 COMPOUND NUMBER RO PW MD CD 55 100 100 100 20 0 0 0 56 90 98 100 20 0 0 °i 57 100 100 100 98 0 90 50 58 100 100 100 100 0 00 0 * 59 100 100 100 80 0 0 0 61 80 90 90 0 0 0 0 62 95 100 100 90 20 20 10 63 100 100 100 80 1 0 20 0 64 90 90 95 40 10 , 0 0 45594/2 Post -emergence COMPOUND NUMBER CG WG RO MD . CD 1 0 0 0 0 0 0 2 90 95 70 100 0 98 3 80 80 80 90 0 60 4 20 0 0 10 0 20 5 90 80 80 90 0 0 6 80 70 70 100 0 70 7 50 50 40 20 10 20 8 80 80 60 90 20 80 9 90 70 30 30 0 20 10 80 70 50 100 100 80 11 50 40 60 80 0 80 12 · 90 80 70 100 20 100 15 70 20 10 0 0 0 16 70 60 40 10 ,10 10 17 80 60 20 30 10 30 18 40 50 10 20 . < 0 0 19 80 70 0 0 0 2Q 20 90 80 70 90 20 100 21 80 70 60 0 0 0 COMPOUND NUMBER CG WG RO MD CD BN 23 100 100 70 90 30 10 24 95 90 80 100 10 10 25 90 90 80 20 10 30 27 80 20 10 0 0 0 31 70 50 10 10 10 20 32 80 80 70 0 0 0 33 80 90 70 80 20 100 34 80 80 80 30 10 80 35 80 80 80 20 20 100 36 80 80 70 80 10 100 37 80 100 70 0 0 80 38 90 90 50 80 20 80 39 80 80 60 10 0 10 40 80 100 60 70 20 100 41 80 90 70 20 0 80 42 90 90 60 20 20 80 43 80 80 60 20 20 70 44 100 100 60 100 70 30 45 100 100 20 100 10 40 46 20 10 0 0 0 10 47 80 60 20 10 0 0 48 100 100 60 50 20 80 50 80 70 50 20 10 80 51 80 70 50 0 0 80 52 80 70 70 80 0 70 45594/2 COMPOUND iUMBER CG WG RO MD CD BN 53 80 7 ■0· * 70 70 0 80 54 80 80 70 90 20 100 55 70 60 50 0 0 80 56 70 70 40 70 0 20 57 80 70 70 60 20 80 58 50 40 20 0 0 60 59 70 60 50 0 * 0 80 61 60 20 0 0 0 0 • 62 100 80 60 80 20 80 63 90 80 60 0 0 80 64 80 95 70 20 ' 0 80 45594/2 The compounds of the present invention are used as pre-emergence or post-emergence herbicides and are applied in a variety of ways at various concentrations. In practice, the compounds are formulated with an inert carrier, utilizing methods well-known to those skilled in the art, thereby making them suitable for application as dusts, sprays, or drenches and the like, in the form and manner required. The mixtures can be dispersed in water with the aid of a wetting agent or they can be employed in organic liquid compositions, oil and water, water in oil emulsions, with or without the addition of wetting, dispersing or emulsifying agents. An herbicldally effective amount depends upon the nature of the seeds or plants to be controlled and the rate of application varies from 0.10 to approximately 50 pounds per acre. The concentration of a compound of the present invention, constituting an effective amount in the best mode of administration in the utility desclosed, is readily determinable by those skilled in the art.

The phytotoxic compositions of this invention employing an herbicldally effective amount of the compound described herein are applied to the plants in the conventional manner. Thus, the I - 21a - dust and liquid compositions can be applied to the plant use of power dusters, boom and hand sprayers and spray dusters. The compositions can also be applied from 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 seed lings, as a typical example, the dust and liquid compositions are applied to the soil according to conventional methods and are dis tributed in the soil to a depth of at least one-half inch below the soil surface. It is not necessary that the phytotoxic compositions be admixed with the soil particles and these compositions can be applied merely to by spraying or sprinkling the surface of the soil. The phytotoxic compositions 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 pene tration of the compositions into the soil as the water is absorbe 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.

The phytotoxic compositions of this invention can also contain other additaments, for example, fertilizers, pesticides and the like, used as adjuvant or in combination with any of the above-described adjuvants. Other phytotoxic compounds useful in combination with the above-described compounds include, for example, 2,4-dichlorophenoxyacetic acids, 2,4,5-trichlorophenoxyaceti acid, 2-methyl-4-chlorophenoxyacetic acid and the salts, esters a amides thereof; triazine derivatives, such as 2,4-bis(3-methoxy-propylamino) -6-methyl-thio-s-triazine; 2-chloro-4-ethylamino-6-isopropylamino-s-triazine, and 2-ethylamino-4-isopropylamino-6- methylmercapto-s-triazine, urea derivatives, such as 3- (3 ,4.-^-Pi-chlorophenyl) -1, 1-dimethyl urea and acetamides such as N,N-di-allyl-o( -chloroacetamide, N-( c^ -chloroacetyl)hexamethyleneimine, and Ν,Ν-diethyl-} -bromoacetamide , and the like; benzoic acids such as 3-amino-2 , 5-dichlorobenzoic ; and thiocarbamates , such as S-propyl dipropylthiocarbamate ; S-ethyldipropylthiocarbamate ; S-ethyl hexahydro-lH-azepine-l-carbothioate and the like. Fertilizers useful in combination with the active ingredients include, for example, ammonium nitrate, urea and superphosphate. Other useful additaments include materials in which plant organisms take root and grow, such as compost, manure, humus, sand and the like .

Various changes and modifications are possible without departing from the spirit and scope of the invention described herein and will be apparent to those skilled in the art to which it pertains. It is accordingly intended that the present invention shall only be limited by the scope of the claims.

Claims

45594/3 WHAT IS CLAIMED IS: » .

1. A compound in vhich the formula is: in which X is chlorine or bromine; R^ and are hydrogen, alkyl having from 1 to 8 carbon atoms, inclusive, haloalkyl having from 1 to 6 carbon atoms, inclusive, in vhich halo is fluorine, bromine and chlorine, alkenyl having from 2 to 6 carbon atoms, inclusive, alkynyl having from 2 to 8 carbon atoms, inclusive, or benzyl; R2 and R^ are hydrogen, alkyl having from 1 to 8 carbon atoms, inclusive, alkenyl having from 2 to 6 carbon atoms, inclusive, haloalkenyl having from 2 to 6 carbon atoms, inclusive, in vhich halo is chlorine or bromine, alkoxyalkyl having from 2 to 8 carbon atoms, inclusive, alkynyl having from 2 to 6 carbon atoms, inclusive, cycloalkyl having from 3 to 8 carbon atoms, inclusive, 1-ethynylcyclohexyl, furfuryl, and tetrahydrofurfuryl; or R1 and R2 together may form an alkylene or alkenylene group having from 2 to 8 carbon atoms, inclusive, the alkylene group being optionally interrupted by an oxygen atom; and R3 and together may form an alkylene or alkenylene group having from 2 to 8 carbon atoms, inclusive, the alkylene group being optionally interrupted by an oxygen atom; and provided that when Rl t R2 , R3 and R4 are each alkyl, then one of Rx or R2 and one of R3 or R4 is other than methyl provided further that only one of Rj^ or R2 is hydrogen and only one of R^ or R, is hydrogen. - 24 -

2. A compound according to Claim 1 in which X is bromine, R^, R3 and R^ are each alkyl. ^

3. A compound according to Claim 2 in which R^ is j methyl, R2 is ethyl, R^ is methyl and R^ is ethyl.

4. A compound according to Claim 2 in which R^ is ethyl, R2 is ethyl, R^ is ethyl and R^ is ethyl.

5. A compound according to Claim 2 in which R^ is n-propyl, R2 is n-propyl, R^ is n-propyl and ^ is n-propyl.

6. 0 A compound according to Claim 1 in which X is bromine, R^, R2, R3 and R^ are each alkenyl.

7. A compound according to Claim 6 in which R^ is · allyl, R2 is allyl, R^ is allyl and R^ is allyl.

8. A compound according to Claim 1 in which X is bromine, R-^ and R3 are each alkyl and R2 and R^ are each halo-alkenyl.

9. A compound according to Claim 8 in which It. md R are each n-propyl and R2 and R^ are each 2-chloroallyl.

10. A compound according to Claim 1 in which X is bromine, R^ and R^ are each alkenyl and R2 and R^ are each halo alkenyl .

11. A compound according to Claim 10 in which R^ and R^ are each allyl and R2 and R^ are each 2-chloroallyl.

12. A compound according to Claim 1 in which X is bromine, R^ and R3 are each alkyl and R2 and R^ are each alkeny ! 45594/2

13. A compound according to Claim 12 in which R^ and are each n-propyl and R^, and R^ are each allyl.

14. ■ 14. A compound according to Claim 1 in which X is bromine, R^ and ^ are each benzyl, 2 and R^ are each hydrogen, r

15. A compound according to Claim 1 in which X ie bromine, R1 end R^ are each hydrogen and Rg and R^ are each alkoxyalkyl.

16. A compound according to Claim 15 in which Rj> and ^ are each methoxypropyl. ·

17.. A compound according" to Claim 1 in which X is chlorine, ^, R2, R3 and R^ are each alkenyl.

18. A compound according to Claim 17 in which R^ is allyl, 2 is allyl, 3 is allyl and ^ is allyl.

19. A compound according to Claim 1 in which X is chlorine, R^ and R3 are each alkenyl and R2 and R^ are each haloalkenyl .

20. A compound according to Claim 17 in which R^ and R^ are each allyl and R2 and ^ .are each 2-chloroallyl. Ιι !

21. A compound according to Claim 1 in which X is chlorine, ^ and ^ are each alkyl and R2 and R^ are each alkynyl ., 26 45594/2 _J

22. A compound according to Claim 21 in which ¾ and R3 are each methyl and ¾ and ¾ are each 1-methylpropargyl.

23. • 23. A compound according to Claim 1 in which X is chlorine, ¾, ¾3 and R4 are each alkyl. " ".''! ■ I

24. ; A compound according to Claim 1 in which Rj^ and R3 are each haloalkyl and R2 and R^ are each hydrogen.

25. A compound according to Claim 1 in which Rj^ and R3 are each alkyl and ^ and R^ are each benzyl.

26. J A compound according to Claim 1 in which Rx and R3 are each alkenyl and R2 and R^ are each cycloalkyl.

27. A compound according to Claim 1 in which and R3 are each alkyl and R2 and R^ are each cycloalkyl.

28. !A compound according to Claim 1 in which R^ R2 , R3 and R^ are each alkynyl .

29. A compound according to Claim 1 in which R^ and R3 are each alkyl and and R^ are. each tetrahydrofurfuryl.

30. A compound according to Claim 1 in which X is bromine, and R^ are each hydrogen and and R^ are each alkyl. - 27 - 45594/2

31. A compound according to Claim 30/ in which and are each hydrogen and Rj and R^ are each ethyl.

32. A compound according to Claim 30 > in which R^ and ^ are each hydrogen and R^ and R^ are each n-propyl.

33. A compound according to Claim j30» in which R^ and Rg are each hydrogen and EL> and R^ are each n-butyl.

34. \ A compound according to Clain. 30 in which R, and R^ are each hydrogen and R2 and R^ are each n-pentyl.

35. ! A compound according to Claim 30 in which'" R^ and. are each hydrogen and R2 and R^;are each methyl.

36. A compound according to Claim* 30 ^n which R^ and R3 are each hydrogen and R2 and R^ are each isopropyl.

37. ' A compound according to Claim 30 in which R^ and are each hydrogen and 2 and ^ are each see,. -butyl.

38. A compound according to Claim 30 in which R^ and are each hydrogen and Rg and R^ are each isobutyl. ■ j

39. ! A compound according to Claimj 30' in which and R^ are each hydrogen and R and R^ are each 1 ,3-dimethylbutyl .

40. A compound according to Claim 31 in which R1 and are each hydrogen and R2 and R^ are each 1-methyl-pentyl. 45594/3

41. A compound according to Claim 30 in which ^ and R3 are each hydrogen and Rj and are each n-hexyl.

42. A compound according to Claim 30 in which and R3 are each hydrogen and Rj and R4 are each 1-methylbutyl.

43. A compound according to Claim 1 in which X is chlorine or bromine; and 2 taken together form an alkylene or alkenylene group having from 2 to 8 carbon atoms, inclusive, the alkylene group being optionally interrupted by an oxygen atom; and R^ taken together form an alkylene or alkenylene group having from 2 to 8 carbon atoms, inclusive, the alkylene group being optionally interrupted by an oxygen atom.

44. A compound according to Claim 43 in which and R2 taken together and R^ and ^ taken together are each an alkenylene group*

45. A compound according to Claim 44 in which X is chlorine, ^ and R2 taken together and ^ and R4 taken together are each 2-pentenylene.

46. A compound according to Claim 44 in which X is bromine, R^ and 62 taken together and and ^ taken together are each 2-pentenylene.

47. A compound according to Claim 44 in which X is chlorine, Rj and Rj taken together and 3 and 4 taken together are each 2-butenylene.

48. A compound according to Claim 43 in which X is bromine, and R2 taken together are ^-oxydiethylene and R^ and R^ taken together areβ-oxydiethylene

49. A compound according to Claim 43 in which X is bromine, R^ and R taken together and R3 and R^ taken together are each alkylene.

50. A compound according to Claim 49 in which R-^ and R2 taken together and R^ and R^ taken together are each penta-methylene .

51. A compound according to Claim 49 in which R^ and taken together and R^ and R^ taken together are each hexa-meth lene.

52. A compound according to Claim 43 in which X is chlorine, ^ and R2 taken together and R^ and R^ taken together are each alkylene.

53. A compound according to Claim 52 in which R^ and 2 taken together and R^ and R^ taken together are each penta-methylene.

54. A compound according to Claim 52 in which R^ and R2 taken together and R^ and R^ taken together are each tetra-methylene .

55. A compound according to Claim 43 in which X i^j£ chlorine, and taken together and and taken together are each 2-methylpentamethylene.

56. A compound according to Claim 43 in which X is chlorine, and R2 taken together and R^ and R^ taken together are each 3-methylpentamethylene .

57. The method of preparing a bis-substituted c^-halo-succinamide comprising the steps reacting an ^ -halosuccinoyl chloride with a primary or secondary amine in a ratio of 1 to 4 at a temperature of from about -30°C. to about -L0°C. and recovery of the resultant product.

58. The method of preparing a bis-substituted o[-halo-succinamide comprising the steps of reacting an -halosuccinoyl chloride with a primary or secondary amine in a ratio of 1 to 2 in the presence of an acid acceptor at a temperature of from about -30°C. to about +10°C. and recovery of the resultant product

59. The method of Claim 57 in which the acid acceptor is triethylamine. 45594/2

60. A method for controlling the growth of undesirable vegetation which comprises applying to the area where control isfe said vegetative growth is desired, an herbicidally effective amount of a compound having the formula: in which X is chlorine or bromine; R-^ and R^ are hydrogen, alkyl having from 1 to 8 carbon atoms, inclusive, haloalkyl having from 1 to 6 carbon atoms, inclusive, in which halo is fluorine, bromine and chlorine, alkenyl having from 2 to 6 carbon atoms, inclusive, alkynyl having from 2 to 8 carbon atoms, inclusive, or benzyl; R2 and R^ are hydrogen, alkyl having from 1 to 8 carbon atoms, inclusive, alkenyl having from 2 to 6 carbon- atoms, inclusive, haloalkenyl having from 2 to 6 carbon atoms, inclusive, in which halo is chlorine or bromine; alkoxyalkyl having from 2 to ¾ carbon atoms, inclusive, alkynyl having from 2 to 6 carbon atoms, inclusive, cycloalkyl having from 3 to 8 carbon atoms, inclusive, 1-ethynylcyclohexyl , furfuryl, and tetrahydro- furfuryl; and R2 taken together along with the nitrogen form a non-aromatic heterocyclic ring having from 2 to 8 carbon atoms, inclusive, and taken together along with the nitrogen form a non-aromatic heterocyclic ring having from 2 to 8 carbon atoms, inclusive; provided that only one of R^ or R is hydrogen and only one of R^ or R^ is hydrogen. -32-

61. A method according to Claim 60 in which X is^r bromine, R^, I^, R3 and are each alkyl.

62. A method according to Claim 61 in which is methyl, R2 is ethyl, R^ is methyl and R^ is ethyl.

63. A method according to Claim 61 in which R^ is ethyl, R2 is ethyl, R^ is ethyl and R^ is ethyl.

64. A method according to Claim 61 in which R^ is n-propyl, R2 is n-propyl, R^ is n-propyl and R^ is n-propyl.

65. A method according to Claim 60 in which X is . bromine, R^, R2, R3 and R^ are each alkenyl.

66. A method according to Claim 65 in which R^ is allyl, R2 is allyl, R3 is allyl and R^ is allyl.

67. A method according to Claim 60 in which X is bromine, R^ and R^ are each alkyl and R2 and R^ are each halo-alkenyl .

68. A method according to Claim 67 in which R^ and R3 are each n-propyl and R2 and R^ are each 2-chloroallyl.

69. A method according to Claim 60 in which X is bromine, R^ and R^ are each alkenyl and R2 and R^ are each halo-alkenyl . ' 45594/2 '¾

70. A method according to Claim 69 in which and R3 are each allyl and R2 and R^ are each 2-chloroallyl .

71. • 71. A method according to Claim 60 in which X is bromine , and R3 are each alkyl and R2 and R^ are each alkenyl

72. A method according to Claim 71 in which ^ and R^ are each n-propyl and R2 and R^ are each allyl . *

73. A method according to Claim 60 in which X is bromine, and R^ are each benzyl, R2 and R^ are each hydrogen.

74. A method according to Claim 60 in which X * ie bromine , ¾ and R are each hydrogen and R, and R are each alkoxyalk l.

75. A method according to Claim 74 in which R2 and R [ are" each methoxypropyl . '

76. . A method according to Claim 60 in which X is chlorine , R^, R2 , R^ and ^ are each alkenyl . .

77. A method according to Claim 76 in which R^ is allyl, R2 is allyl, R^ is allyl and R^ is allyl .

78. A method according to Claim 60 in which X is chlorine, R^ and R^ are each alkenyl and R2 and R^ are each haloalkenyl . - 34 - r

79. A method according to Claim 76 in which an > are each allyl and R2 and R^ are each 2-chloroallyl.

80. A method according to Claim 60 in which X is chlorine, R^ and R^ are each alkyl and R2 and R^ are each alkynyl .

81. A method according to Claim 80 in which R^ and R^ are each methyl and R and R^ are each 1-methylpropargyl.

82. A method according to Claim 60 in which X is chlorine, R^, R , R^ and R^ are each alkyl.

83. A method according to Claim 82 in which R^ is methyl, R2 is methyl, R^ is methyl and R^ is methyl.

84. A method according to Claim 60 in which R^ and R^ are each haloalkyl and R and R^ are each hydrogen.

85. A method according to Claim 60 in which and R^ are each alkyl and R2 and R^ are each benzyl.

86. A method according to Claim 60 in which R^ and R^ are each alkenyl and R2 and R^ are each cycloalkyl.

87. A method according to Claim 60 in which R^ and R^ are each alkyl and R and R^ are each cycloalkyl.

88. A method according to Claim 60 in which R^ , R j, R3 and R^ are each alkynyl.

89. A method according to Claim 60 in which R^ and R^ are each alkyl and R2 and R^ are each tetrahydrofurfuryl.

90. A method according to Claim 60 in which X is bromine, R^ and R^ are each hydrogen and R2 and R^ are each alkyl

91. A method according to Claim 90 in which R^ and R3 are each hydrogen and R2 and R^ are each ethyl.

92. A method according to Claim 90 in which R^ and are each hydrogen and R2 and R^ are each n-propyl.

93. A method according to Claim 90 in which R^ and R-j are each hydrogen and R and R^ are each n-butyl.

94. A method according to Claim 90 in which R^ and R^ are each hydrogen and R2 and R^ are each n-pentyl.

95. A method according to Claim 90 in which R^ and R^ are each hydrogen and R2 and R^ are each methyl.

96. A method according to Claim 90 in which R^ and R^ are each hydrogen and R2 and R^ are each isopropyl.

97. A method according to Claim 90 in which R and each hydrogen and R and R^ are each sec. -butyl. 45594/2

98. A method according to Claim 90 in which and R3 are each hydrogen and R2 and ^ are each Isobutyl.

99. A method according to Claim 90 in which R^ and j are each hydrogen and TS^ and ^ are each l-methylpentyl.

100. A method according to Claim 90 in which R^ and R3 are each hydrogen and and R^ are each n-hexyl.

101. A method according to Claim 90 in which ^ and are each hydrogen and R2 and R^ are each 1-raethylbutyl.

102. A method according to Claim 60 in which X is chlorine or bromine; R^ and j taken together form an alkylene or alkenylene group having from 2 to 8 carbon atoms. Inclusive, the alkylene group being optionally interrupted by an oxygen atom; and R^ and ^ taken together form an alkylene or alkenylene group having from 2 to 8 carbon atoms, inclusive, the alkylene group being optionally interrupted by an oxygen atom.

103. A method according to Claim 102 in which Rj, and &2 take together and and 4 taken together are each an alkenylene group.

104. A method according to Claim 103 in which X is chlorine, and j taken together and R3 and taken together are each 2-pentenylene.

105. A method according to Claim 103 in which X is bromine , St., and taken together and 3 and ^ taken together are each 2-penten lene.

106. A method according to Claim 103 in which X is „ chlorine; and taken together and and R^ taken together are each 2-butenylene.

107. A method according to Claim 102 in which X is bromine, RR^^ aanndd RR22 ttaakkeenn ttooggeetthheerr aarree ^ -oxydiethylene and ^ and R^ taken together are -oxydiethylene.

108. A method according to Claim 102 in which X is bromine, R^ and R2 taken together and R^ and R^ taken together are each alkylene.

109. A method according to Claim 108 in which R^ and R2 taken together and R^ and R^ taken together are each penta-methylene.

110. A method according to Claim 108 in which R^ and ¾2 taken together and R^ and R^ taken together are each hexa-methylene.

111. A method according to Claim 102 in which X is chlorine, R^ and R2 taken together and R^ and R^ taken together are each alkylene.

112. A method according to Claim 111 in which Rj^ and R2 taken together and R^ and ^ taken together are each penta-methylene. *

113. A method according to Claim 111 in which ancj R2 taken together and and R^ taken together are each tetra-methylene .

114. A method according to Claim 102 in which X is chlorine, R^ and R2 taken together and R-j and taken together are each 2-methylpentamethylene.

115. A method according to Claim 102 in which X is chlorine, R^ and R2 taken together and R^ and R^ taken together are each 3-methylpentamethylene.