Dioxolane Substituted Amides

This invention relates to new compositions of matter and more specifically relates to new chemical compounds of the formula ##STR2## wherein R.sup.1 is selected from the group consisting of hydrogen and alkyl; X is halogen; R.sup.2 is selected from the group consisting of alkyl, alkenyl and alkynyl; n is the integer 1 or 2; and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each selected from the group consisting of hydrogen and alkyl.

The compounds of the present invention are useful as herbicides and are exceptionally suitable as preemergence grass herbicides. Moreover the subject compounds are useful for stunting the growth of ornamental turf reducing the need for mowing.

In a preferred embodiment of the present invention R.sup.1 is selected from the group consisting of hydrogen and lower alkyl; X is selected from the group consisting of chlorine and bromine; R.sup.2 is selected from the group consisting of alkyl of up to ten carbon atoms, lower alkenyl and lower alkynyl; n is the integer 1 or 2; and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each selected from the group consisting of hydrogen and lower alkyl.

The term lower as used herein designates a straight or branched carbon chain of up to six carbon atoms.

The compounds of the present invention can be prepared by reacting a compound of the formula ##STR3## wherein R.sup.2, n, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as heretofore described, with an .alpha.-haloalkanoyl chloride of the formula ##STR4## wherein R.sup.1 and X are as heretofore described. This reaction can be effected by combining a compound of formula II with an about equimolar or slight excess molar amount of a compound of formula III in an inert organic reaction medium, such as benzene, in the presence of an acid acceptor, such as an alkali metal carbonate or bicarbonate or a tertiary amine, at a temperature of about -10.degree. C. to about 25.degree. C. and stirring the resulting mixture for a period of from about 15 to about 120 minutes. After this time the reaction mixture can be washed with water to remove inorganic salts and stripped of solvent to yield the desired product. This product can then be used as such or can be further purified by conventional means.

The compounds of formula II can be prepared by reacting a substituted amine of the formula ##STR5## wherein R.sup.2 is as heretofore described with a compound of the formula ##STR6## wherein Y is chlorine or bromine and n, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as heretofore described. This reaction can be effected by combining the compound of formula V with an excess molar amount of the amine of formula IV and heating the mixture with agitation for a period of from 1/2 to 8 hours. When a very low boiling amine is used a pressurized vessel can be preferably utilized. After this time strong inorganic base such as aqueous base is added to the reaction mixture to liberate the free amine from its hydrochloride. The organic phase is then separated from the aqueous phase, dried over anhydrous magnesium sulfate and distilled to yield the desired product.

The compounds of formula V when not available can be prepared by reacting an acetal of the formula ##STR7## wherein Y and n are as heretofore described and R.sup.7 and R.sup.8 are methyl or ethyl, with a diol of the formula ##STR8## wherein R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as heretofore described. This reaction can be effected by combining the compound of formula VI with the compound of formula VII in about equimolar amounts and in the presence of an acid catalyst such as sulfuric acid or toluene sulfonic acid under anhydrous conditions. The mixture can be heated at reflux for a period of from about 1 to about 4 hours. After this time the reaction mixture can be distilled under reduced pressure to yield the desired product.

The compounds of the present invention can also be prepared by reacting an acetal of the formula ##STR9## wherein R.sup.1, X, R.sup.2, n, R.sup.7 and R.sup.8 are as heretofore described with an about equimolar amount of the diol of formula VII. This reaction can be effected by combining the reactants in the presence of a catalytic amount of toluene sulfonic acid under anhydrous conditions. The reaction mixture can be heated and the alcohol removed by distillation as it is formed. After no more alcohol is given off sodium carbonate can be added and the reaction mixture distilled to yield the desired product.

The compounds of formula VIII can be prepared by reacting a compound of the formula ##STR10## wherein R.sup.2, n, R.sup.7 and R.sup.8 are as heretofore described, with a compound of formula III. This reaction can be effected in the same manner as the reaction between compound II and III described above.

The compounds of formula IX can be prepared by reacting the amine of formula IV with an about equimolar amount of the acetal of formula VI. This reaction can be effected by combining the reactants in an inert organic reaction medium in the presence of an acid acceptor. The reaction mixture can be heated at reflux for a period of from 2 to 24 hours. After this time the mixture is filtered and stripped of solvent to yield the desired product.

Exemplary suitable diols of formula VII for preparing the compounds of the present invention are ethandiol-1,2, propandiol-1,2, butandiol-1,2, pentandiol-1,2, hexandiol-1,2, heptandiol-1,2, octandiol-1,2, butandiol-2,3, pentandiol-2,3, hexandiol-2,3, octandiol-2,3, hexandiol-3,4, octandiol-3,4, octandiol-4,5, methylbutandiol-1,2 and the like.

Exemplary suitable amines of formula IV are methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, allylamine, 2-butenylamine, 2-pentenylamine, 3-pentenylamine, 4-hexenylamine, 5-hexenylamine, propargylamine, 2-butynylamine, 3-butynylamine, 1,1-dimethylpropargylamine, 1,1-diethylpropargylamine, 4-hexynylamine, isopropylamine, t-butylamine and the like.

Exemplary suitable .alpha.-haloalkanoyl chlorides of formula III for preparing the compounds of this invention are chloroacetyl chloride, .alpha.-chloropropanoyl chloride, .alpha.-bromobutanoyl chloride, .alpha.-chloropentanoyl chloride, .alpha.-chlorohexanoyl chloride, .alpha.-chloro-.beta.-methylbutanoyl chloride, .alpha.-chloroheptanoyl chloride and the like.

The dimethylacetal of 2-methylaminoacetaldehyde (50 grams; 0.42 mole), methylene chloride (200 ml) and triethylamine (46.6 grams; 0.462 mole) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer, addition funnel and calcium chloride drying tube. The reaction mixture was cooled to about -20.degree. C. and chloroacetyl chloride (49.7 grams; 0.44 mole) dissolved in methylene chloride (29 ml) was added dropwise with stirring. After the addition was completed stirring was continued for a period of about 60 minutes at a temperature of from -20.degree. C. to -10.degree. C. The reaction mixture was then stirred at room temperature overnight. After this time ether (125 ml) was added and the reaction mixture was filtered. The filtrate was then washed with water and dilute aqueous sodium hydroxide. The washed solution was dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-methyl-N-(2,2-dimethoxyethyl)-.alpha.-chloroacetamide having a boiling point of 117.degree. to 119.degree. C. at 0.30 mm of Hg pressure.

N-Methyl-N-(2,2-dimethoxyethyl)-.alpha.-chloroacetamide (19.5 grams; 0.10 mole), ethylene glycol (6.82 grams; 0.11 mole) and 10 drops of a solution of toluene sulfonic acid (1 gram) in ether (100 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and distillation head. The mixture was heated at 100.degree. to 110.degree. C. with stirring and the methanol removed as it was formed. After no more methanol was given off the reaction mixture was cooled to room temperature and was stirred with about 2 grams of sodium carbonate for a period of about 1 hour. After this time the reaction mixture was filtered and the filtrate was distilled under reduced pressure to yield the desired product N-methyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide having a boiling point of 119.degree. to 124.degree. C. at a pressure of 0.15 to 0.30 mm of Hg.

2-Bromomethyl-1,3-dioxolane (15 grams; 0.09 mole) and isopropylamine (38 ml; 0.45 mole) were charged into a Parr Shaker. The shaker was sealed and was heated with an infrared lamp to a pressure of about 50 p.s.i. Heating was stopped and the reaction mixture was shaken for a period of about 1/2 hour. After this time aqueous sodium hydroxide (12 ml; 50% concentration) was added to the reaction mixture with stirring. The organic phase was then separated from the aqueous phase, was dried over anhydrous magnesium sulfate and distilled under reduced pressure to yield the desired product N-isopropyl-N-(1,3-dioxolan-2-ylmethyl)amine as an oil.

N-Isopropyl-N-(1,3-dioxolan-2-ylmethyl)amine (9.5 grams) benzene (100 ml), water (100 ml) and sodium carbonate (10 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The mixture was cooled to about 5.degree. to 10.degree. C. and chloroacetyl chloride (5 ml) was added dropwise with stirring. After the addition was completed stirring was continued until the reaction mixture reached room temperature. After this time the organic phase was separated from the aqueous phase and was washed with water. The washed solution was then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-isopropyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide as an oil.

2-Bromomethyl-1,3-dioxolane (15 grams; 0.09 mole) and ethylamine (74 ml; 1.65 mole) were charged into a Parr Shaker. The shaker was sealed and was heated with an infra-red lamp to a pressure of about 50 p.s.i. Heating was stopped and the reaction mixture was shaken for a period of about 1/2 hour. After this time aqueous sodium hydroxide (12 ml; 50% concentration) was added to the reaction mixture with stirring. The organic phase was then separated from the aqueous phase, was dried over anhydrous magnesium sulfate and distilled under reduced pressure to yield the desired product N-ethyl-N-(1,3-dioxolan-2-ylmethyl)amine as an oil.

N-Ethyl-N-(1,3-dioxolan-2-ylmethyl)amine (50 grams), benzene (100 ml), water (100 ml) and sodium carbonate (5.0 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The mixture was cooled to about 5.degree. to 10.degree. C. and chloroacetyl chloride (3 ml) was added dropwise with stirring. After the addition was completed stirring was continued until the reaction mixture reached room temperature. After this time the organic phase was separated from the aqueous phase and was washed with water. The washed solution was then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-ethyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide as an oil.

2-Bromomethyl-1,3-dioxolane (20 grams) and n-propylamine (100 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at a temperature of about 100.degree. C. for a period of about 3 hours. After this time sodium hydroxide (10 grams) dissolved in water (100 ml) was added and the resulting mixture was stirred for a period of about 30 minutes. The reaction mixture was then extracted with ether and the ether solution separated and dried over magnesium sulfate. The dried solution was filtered and stripped of solvent to yield the desired product N-n-propyl-N-(1,3-dioxolan-2-ylmethyl)amine an an oil.

N-n-Propyl-N-(1,3-dioxolan-2-ylmethyl)amine (10.5 grams), benzene (100 ml), water (100 ml) and sodium carbonate (8 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The mixture was cooled to about 5.degree. to 10.degree. C. and chloroacetyl chloride (5.5 ml) was added dropwise with stirring. After the addition was completed stirring was continued until the reaction mixture reached room temperature. After this time the organic phase was separated from the aqueous phase and was washed with water. The washed solution was then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-n-propyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide as an oil.

2-Bromomethyl-1,3-dioxolane (20 grams) and N-(diethylmethyl)amine (40 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at a temperature of about 100.degree. C. for a period of about 3 hours. After this time sodium hydroxide (10 grams) dissolved in water (100 ml) was added and the resulting mixture was stirred for a period of about 30 minutes. The reaction mixture was then extracted with ether and the ether solution was separated and dried over magnesium sulfate. The dried solution was filtered and stripped of solvent to yield the desired product N-diethylmethyl-N-(1,3-dioxolan-2-ylmethyl)-amine as an oil.

N-Diethylmethyl-N-(1,3-dioxolan-2-ylmethyl)amine (8.2 grams), benzene (100 ml), water (100 ml) and sodium carbonate (6 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The mixture was cooled to about 5.degree. to 10.degree. C. and chloroacetyl chloride (3.8 ml) was added dropwise with stirring. After the addition was completed stirring was continued until the reaction mixture reached room temperature. After this time the organic phase was separated from the aqueous phase and was washed with water. The washed solution was then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-diethyl-methyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide as an oil.

2-Bromomethyl-1,3-dioxolane (20 grams) and sec-butylamine (120 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at a temperature of about 100.degree. C. for a period of about 3 hours. After this time sodium hydroxide (10 grams) dissolved in water (100 ml) was added and the resulting mixture was stirred for a period of about 30 minutes. The reaction mixture was then extracted with ether and the ether solution was separated and dried over magnesium sulfate. The dried solution was filtered and stripped of solvent to yield the desired product N-sec-butyl-N-(1,3-dioxolan-2-ylmethyl)amine as an oil.

N-Sec-Butyl-N-(1,3-dioxolan-2-ylmethyl)amine (12.0 grams, benzene (100 ml), water (100 ml) and sodium carbonate (10 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The mixture was cooled to about 5.degree. to 10.degree. C. and chloroacetyl chloride (6.0 ml) was added dropwise with stirring. After the addition was completed stirring was continued until the reaction mixture reached room temperature. After this time the organic phase was separated from the aqueous phase and was washed with water. The washed solution was then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-sec-butyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide as an oil.

2-Bromomethyl-1,3-dioxolane (20 grams) and n-hexylamine (100 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at a temperature of about 100.degree. C. for a period of about 3 hours. After this time sodium hydroxide (10 grams) dissolved in water (100 ml) was added and the resulting mixture was stirred for a period of about 30 minutes. The reaction mixture was then extracted with ether and the ether solution was separated and dried over magnesium sulfate. The dried solution was filtered and stripped of solvent to yield the desired product N-n-hexyl-N-(1,3-dioxolan-2-ylmethyl)amine as an oil.

N-n-Hexyl-N-(1,3-dioxolan-2-ylmethyl)amine (12.0 grams), benzene (100 ml), water (100 ml) and sodium carbonate (8 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The mixture was cooled to about 5.degree. to 10.degree. C. and chloroacetyl chloride (5.0 ml) was added dropwise with stirring. After the addition was completed stirring was continued until the reaction mixture reached room temperature. After this time the organic phase was separated from the aqueous phase and was washed with water. The washed solution was then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-n-hexyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide as an oil.

The diethylacetal of 2-bromoacetaldehyde (118 grams) and isopropylamine (260 ml) were charged into a Parr Shaker. The shaker was sealed and heated with an infra-red lamp with agitation to a pressure of about 50 p.s.i. Heating was then stopped and the mixture was shaken for an additional 30 minutes. After this time aqueous sodium hydroxide (90 ml; 50% concentration was added to the reaction mixture with stirring. The organic phase was separated from the aqueous phase, was dried and distilled under reduced pressure to yield the desired product the diethylacetal of 2-isopropylaminoacetaldehyde as the residue.

The diethylacetal of 2-isopropylaminoacetaldehyde (68 grams), benzene (100 ml), water (100 ml) and sodium carbonate (44 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture was cooled to a temperature of 5.degree. to 10.degree. C. and chloroacetyl chloride (30 ml) was added dropwise with stirring. Stirring was continued until the reaction mixture reached room temperature. After this time the organic phase was separated from the aqueous phase, was washed with water and dried over anhydrous magnesium sulfate. The dried solution was filtered and the filtrate stripped of solvent to yield the desired product N-isopropyl-N-(2,2-diethoxyethyl)-.alpha.-chloroacetamide as the residue.

N-Isopropyl-N-(2,2-diethoxyethyl)-.alpha.-chloroacetamide (10 grams), butandiol-1,2 (3.56 ml) and trace amounts of toluenesulfonic acid were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux until no more ethanol was given off. After this time sodium carbonate (1 gram) was added to the mixture with stirring and the resulting mixture was distilled to yield the desired product N-isopropyl-N-(4-ethyl-1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide having a boiling point of 140.degree. C. at 1 mm of Hg pressure.

2-Bromomethyl-1,3-dioxolane (20 grams) and allylamine (70 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at a temperature of about 100.degree. C. for a period of about 3 hours. After this time sodium hydroxide (10 grams) dissolved in water (100 ml) was added and the resulting mixture was stirred for a period of about 30 minutes. The reaction mixture was then extracted with ether and the ether solution was separated and dried over magnesium sulfate. The dried solution was filtered and stripped of solvent to yield the desired product N-Allyl-N-(1,3-dioxolan-2-ylmethyl)amine as an oil.

N-Allyl-N-(1,3-dioxolan-2-ylmethyl)amine (9.2 grams), benzene (100 ml), water (100 ml) and sodium carbonate (8 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The mixture was cooled to about 5.degree. to 10.degree. C. and chloroacetyl chloride (5 ml) was added dropwise with stirring. After the addition was completed stirring was continued until the reaction mixture reached room temperature. After this time the organic phase was separated from the aqueous phase and was washed with water. The washed solution was then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-allyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide as an oil.

N-(2,2-Dimethoxyethyl)amine (23 grams), triethylamine (31 ml) and benzene (100 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. 1-Bromo-2-propyne (16.5 grams) was added dropwise with stirring to the reaction mixture at room temperature. After the addition was completed stirring was continued for a period of about 1 hour. After this time the reaction mixture was filtered and stripped of solvent. The residue was then distilled to yield the desired product N-propargyl-N-(2,2-dimethoxyethyl)amine having a boiling point of 70.degree. C. at 1 mm of Hg pressure.

N-Propargyl-N-(2,2-dimethoxyethyl)amine (9 grams), benzene (100 ml), water (100 ml) and sodium carbonate (8 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture was cooled to a temperature of 5.degree. to 10.degree. C. and chloroacetyl chloride (5 ml) was added dropwise with stirring. Stirring was then continued until the reaction mixture reached room temperature. After this time the organic phase was separated from the aqueous phase, was washed with water and was dried. The dried solution was then filtered and the filtrate stripped of solvent to yield the desired product N-propargyl-N-(2,2-dimethoxyethyl)-.alpha.-chloroacetamide as the residue.

N-Propargyl-N-(2,2-dimethoxyethyl)-.alpha.-chloroacetamide (8.5 grams), ethandiol-1,2 (2.16 ml) and trace amounts of toluenesulfonic acid were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux until no more ethanol was given off. After this time sodium carbonate (1 gram) was added to the mixture with stirring and the resulting mixture was distilled to yield the desired product N-propargyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide having a boiling point of 160.degree. to 165.degree. C. at 1 mm of Hg pressure.

N-Isopropyl-N-(2,2-diethoxyethyl)-.alpha.-chloroacetamide (10 grams), propandiol-1,2 (2.9 ml) and trace amounts of toluenesulfonic acid were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux until no more ethanol was given off. After this time sodium carbonate (1 gram) was added to the mixture with stirring and the resulting mixture was distilled to yield the desired product N-propargyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide having a boiling point of 155.degree. to 160.degree. C. at 1 mm of Hg pressure.

2-Bromomethyl-1,3-dioxolane (20 grams) and n-butylamine (120 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at a temperature of about 100.degree. C. for a period of about 3 hours. After this time sodium hydroxide (10 grams) dissolved in water (100 ml) was added and the resulting mixture was stirred for a period of about 30 minutes. The reaction mixture was then extracted with ether and the ether solution was separated and dried over magnesium sulfate. The dried solution was filtered and stripped of solvent to yield the desired product N-n-butyl-N-(1,3-dioxolan-2-ylmethyl)amine as an oil.

N-n-Butyl-N-(1,3-dioxolan-2-ylmethyl)amine (12.5 grams), benzene (100 ml), water (100 ml) and sodium carbonate (10 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The mixture was cooled to about 5.degree. to 10.degree. C. and chloroacetyl chloride (6 ml) was added dropwise with stirring. After the addition was completed stirring was continued until the reaction mixture reached room temperature. After this time the organic phase was separated from the aqueous phase and was washed with water. The washed solution was then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-n-butyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide as an oil.

The diethylacetal of 2-bromoacetaldehyde (40 grams) and 1-methylhexylamine (50 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at a temperature of about 100.degree. C. for a period of about 3 hours. After this time sodium hydroxide (10 grams) dissolved in water (100 ml) was added and the resulting mixture stirred for about 30 minutes. The reaction mixture was then extracted with ether. The ether extract was separated, dried over magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product the diethylacetal of 2-(1-methylhexylamino)acetaldehyde having a boiling point of 110.degree. C. at 1 mm of Hg pressure.

The diethylacetal of 2-(1-methylhexylamino)acetaldehyde (33.5 grams), benzene (100 ml), water (100 ml) and sodium carbonate (17 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture was cooled to a temperature of 5.degree. to 10.degree. C. and chloroacetyl chloride (11 ml) was added dropwise with stirring. Stirring was continued until the reaction mixture reached room temperature. After this time the organic phase was separated from the aqueous phase, was washed with water and dried over anhydrous magnesium sulfate. The dried solution was filtered and the filtrate stripped of solvent to yield the desired product N-(1-methylhexylamino)-N-(2,2-diethoxyethyl)-.alpha.-chloroacetamide as the residue.

N-(1-Methylhexyl)-N-(2,2-diethoxyethyl)-.alpha.-chloroacetamide (10 grams), ethylene glycol (2.0 grams) and trace amounts of toluenesulfonic acid were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux until no more ethanol was given off. After this time sodium carbonate (1 gram) was added to the mixture with stirring and the resulting mixture was distilled to yield the desired product N-(1-methylhexyl)-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide having a boiling point of 173.degree. C. at 1 mm of Hg pressure.

The diethylacetal of 2-bromoacetaldehyde (40 grams) and 1,4-dimethylpentylamine (50 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at a temperature of about 100.degree. C. for a period of about 3 hours. After this time sodium hydroxide (10 grams) dissolved in water (100 ml) was added and the resulting mixture stirred for about 30 minutes. The reaction mixture was then extracted with ether. The ether extract was separated, dried over magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product the diethylacetal of 2-(1,4-dimethylpentylamino)acetaldehyde having a boiling point of 95.degree. C. at 1 mm of Hg pressure.

The diethylacetal of 2-(1,4-dimethylpentylamino)acetaldehyde (22.5 grams), benzene (100 ml), water (100 ml) and sodium carbonate (14 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture was cooled to a temperature of 5.degree. to 10.degree. C. and chloroacetyl chloride (8 ml) was added dropwise with stirring. Stirring was continued until the reaction mixture reached room temperature. After this time the organic phase was separated from the aqueous phase, was washed with water and dried over anhydrous magnesium sulfate. The dried solution was filtered and the filtrate stripped of solvent to yield the desired product N-(1,4-dimethylpentyl)-N-(2,2-diethoxyethyl)-.alpha.-chloroacetamide as the residue.

N-(1,4-Dimethylpentyl)-N-(2,2-diethoxyethyl)-.alpha.-chloroacetamide (10 grams), ethylene glycol (2 grams) and trace amounts of toluenesulfonic acid were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux until no more ethanol was given off. After this time sodium carbonate (1 gram) was added to the mixture with stirring and the resulting mixture was distilled to yield the desired product N-(1,4-dimethylpentyl)-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide having a boiling point of 200.degree. to 205.degree. C. at 1 mm of Hg pressure.

2-Bromomethyl-4,5-dimethyl-1,3-dioxolane (20 grams) and 1,1-dimethylprop-2-ynylamine (100 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at a temperature of about 100.degree. C. for a period of about 3 hours. After this time sodium hydroxide (10 grams) dissolved in water (100 ml) is added and the resulting mixture is stirred for a period of about 30 minutes. The reaction mixture is then extracted with ether. The ether extract is dried over anhydrous magnesium sulfate, filtered and stripped of solvent to yield the desired product N-(1,1-dimethylprop-2-ynyl)-N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)amine.

N-(1,1-Dimethylprop-2-ynyl)-N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)amine (10 grams), benzene (100 ml), water (100 ml) and sodium carbonate (8 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is cooled to a temperature of 5.degree. to 10.degree. C. and .alpha.-bromopropionyl chloride (7 grams) is added dropwise with stirring. After the addition is completed stirring is continued until the reaction mixture reaches room temperature. After this time the organic phase is separated from the aqueous phase and is washed with water. The washed solution is then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-(1,1-dimethylprop-2-ynyl)-N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-.alph a.-bromopropionamide.

2-Bromoethyl-4,4,5,5-tetramethyl-1,3-dioxolane (20 grams) and 4-hexenylamine (100 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at a temperature of about 100.degree. C. for a period of about 3 hours. After this time sodium hydroxide (10 grams) dissolved in water (100 ml) is added and the resulting mixture is stirred for a period of about 30 minutes. The reaction mixture is then extracted with ether. The ether extract is dried over anhydrous magnesium sulfate, filtered and stripped of solvent to yield the desired product N-hex-4-enyl-N-(4,4,5,5-tetramethyl-1,3-dioxolan-2-ylethyl)amine.

N-Hex-4-enyl-N-(4,4,5,5-tetramethyl-1,3-dioxolan-2-ylethyl)-amine (10 grams), benzene (100 ml), water (100 ml) and sodium carbonate (8 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is cooled to a temperature of 5.degree. to 10.degree. C. and .alpha.-chlorobutanoyl chloride (7 grams) is added dropwise with stirring. After the addition is completed stirring is continued until the reaction mixture reaches room temperature. After this time the organic phase is separated from the aqueous phase and is washed with water. The washed solution is then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-hex-4-enyl-N-(4,4,5,5-tetramethyl-1,3-dioxolan-2-ylethyl)-.alpha.-chloro butanamide.

Additional exemplary compounds within the scope of the present invention which can be prepared by the procedures of the foregoing invention are:

N-methyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-bromoacetamide,

N-ethyl-N-(4-methyl-1,3-dioxolan-2-ylmethyl)-.alpha.-chloropropionamide,

N-propyl-N-(4-ethyl-1,3-dioxolan-2-ylmethyl)-.alpha.-bromobutanamide,

N-butyl-N-(4-propyl-1,3-dioxolan-2-ylmethyl)-.alpha.-chloropentanamide,

N-pentyl-N-(4-butyl-1,3-dioxolan-2-ylmethyl)-.alpha.-chlorohexanamide,

N-hexyl-N-(4-pentyl-1,3-dioxolan-2-ylmethyl)-.alpha.-chloroheptanamide,

N-heptyl-N-(4-hexyl-1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide,

N-octyl-N-(4,4-diethyl-1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide,

N-nonyl-N-(4,5-diethyl-1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide,

N-decyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide,

N-but-3-enyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide,

N-pent-3-enyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide,

N-hex-3-enyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide,

N-but-3-ynyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide,

N-pent-4-ynyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide,

N-hex-5-ynyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide,

methyl-N-(1,3-dioxolan-2-ylmethyl)-.alpha.-chloroacetamide.

For practical use as herbicides the compounds of this invention are generally incorporated into herbicidal compositions which comprise an inert carrier and a herbicidally toxic amount of such a compound. Such herbicidal compositions, which can also be called formulations, enable the active compound to be applied conveniently to the site of the weed infestation in any desired quantity. These compositions can be solids such as dusts, granules, or wettable powders; or they can be liquids such as solutions, aerosols, or emulsifiable concentrates.

For example, dusts can be prepared by grinding and blending the active compound with a solid inert carrier such as the talcs, clays, silicas, pyrophyllite, and the like. Granular formulations can be prepared by impregnating the compound, usually dissolved in a suitable solvent, onto and into granulated carriers such as the attapulgites or the vermiculites, usually of a particle size range of from about 0.3 to 1.5 mm. Wettable powders, which can be dispersed in water or oil to any desired concentration of the active compound, can be prepared by incorporating wetting agents into concentrated dust compositions.

In some cases the active compounds are sufficiently soluble in common organic solvents such as kerosene or xylene so that they can be used directly as solutions in these solvents. Frequently, solutions of herbicides can be dispersed under super-atmospheric pressure as aerosols. However, preferred liquid herbicidal compositions are emulsifiable concentrates, which comprise an active compound according to this invention and as the inert carrier, a solvent and an emulsifier. Such emulsifiable concentrates can be extended with water and/or oil to any desired concentration of active compound for application as sprays to the site of the weed infestation. The emulsifiers most commonly used in these concentrates are nonionic or mixtures of nonionic with anionic surface-active agents. With the use of some emulsifier systems an inverted emulsion (water in oil) can be prepared for direct application to weed infestations.

A typical herbicidal composition according to this invention is illustrated by the following example, in which the quantities are in parts by weight.

The above ingredients are mixed in a mechanical grinder-blender and are ground until a homogeneous, free-flowing dust of the desired particle size is obtained. This dust is suitable for direct application to the site of the weed infestation.

The compounds of this invention can be applied as herbicides in any manner recognized in the art. One method for the control of weeds comprises contacting the locus of said weeds with a herbicidal composition comprising an inert carrier and as an essential active ingredient, in a quantity which is herbicidally toxic to said weeds, a compound of the present invention. The concentration of the new compounds of this invention in the herbicidal compositions will vary greatly with the type of formulation and the purpose for which it is designed, but generally the herbicidal compositions will comprise from about 0.05 to about 95 percent by weight of the active compounds of this invention. In a preferred embodiment of this invention, the herbicidal compositions will comprise from about 5 to about 75 percent by weight of the active compound. The compositions can also comprise such additional substances as other pesticides, such as insecticides, nematocides, fungicides, and the like; stabilizers, spreaders, deactivators, adhesives, stickers, fertilizers, activators, synergists, and the like.

The compounds of the present invention are also useful when combined with other herbicides and/or defoliants, dessicants, growth inhibitors, and the like in the herbicidal compositions heretofore described. These other materials can comprise from about 5% to about 95% of the active ingredients in the herbicidal compositions. Use of combinations of these other herbicides and/or defoliants, dessicants, etc. with the compounds of the present invention provide herbicidal compositions which are more effective in controlling weeds and often provide results unattainable with separate compositions of the individual herbicides. The other herbicides, defoliants, dessicants and plant growth inhibitors, with which the compounds of this invention can be used in the herbicidal compositions to control weeds, can include chlorophenoxy herbicides such as 2,4-D, 2,4,5-T, MCPA, MCPB, 4(2,4-DB), 2,4-DEB, 4-CPB, 4-CPA, 4-CPP, 2,4,5-TB, 2,4,5-TES, 3,4-DA, silvex and the like; carbamate herbicides such as IPC, CIPC, swep, barban, BCPC, CEPC, CPPC, and the like; thiocarbamate and dithiocarbamate herbicides such as CDEC, metham sodium, EPTC, diallate, PEBC, perbulate, vernolate and the like; substituted urea herbicides such as norea, siduron, dichloral urea, chloroxuron, cycluron, fenuron, monuron, monuron TCA, diuron, linuron, monolinuron, neburon, buturon, trimeturon and the like; symmetrical triazine herbicides such as simazine, chlorazine, atraone, desmetryne, norazine, ipazine, prometryn, atrazine, trietazine, simetone, prometone, propazine, ametryne and the like; chloroacetamide herbicides such as alpha-chloro-N,N-dimethylacetamide, CDEA, CDAA, alpha-chloro-N-isopropylacetamide, 2-chloro-N-isopropylacetanilide, 4-(chloroacetyl)morpholine, 1-(chloroacetyl)piperidine and the like; chlorinated aliphatic acid herbicides such as TCA, dalapon, 2,3-dichloropropionic acid, 2,2,3-TPA and the like; chlorinated benzoic acid and phenylacetic acid herbicides such as 2,3,6-TBA, 2,3,5,6-TBA, dicamba tricamba, amiben, fenac, PBA, 2-methoxy-3,6-dichlorophenylacetic acid, 3-methoxy-2,6-dichlorophenylacetic acid, 2-methoxy-3,5,6-trichlorophenylacetic acid, 2,4-dichloro-3-nitrobenzoic acid and the like; and such compounds as aminotriazole, maleic hydrazide, phenyl mercuric acetate, endothal, biuret, technical chlordane, dimethyl 2,3,5,6-tetrachloroterephthalate, diquat, erbon, DNC, DNBP, dichlobenil, DPA, diphenamid, dipropalin, trifluralin, solan, dicryl, merphos, DMPA, DSMA, MSMA, potassium azide, acrolein, benefin, bensulide, AMS, bromacil, 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione, bromoxynil, cacodylic acid, CMA, CPMF, cypromid, DCB, DCPA, dichlone, diphenatril, DMTT, DNAP, EBEP, EXD, HCA, ioxynil, IPX, isocil, potassium cyanate, MAA, MAMA, MCPES, MCPP, MH, molinate, NPA, OCH, paraquat, PCP, picloram, DPA, PCA, pyrichlor, sesone, terbacil, terbutol, TCBA, brominil, CP-50144, H-176-1, H-732, M-2901, planavin, sodium tetraborate, calcium cyanamid, DEF, ethyl xanthogen disulfide, sindone, sindone B, propanil and the like. Such herbicides can also be used in the methods and compositions of this invention in the form of their salts, esters, amides, and other derivatives whenever applicable to the particular parent compounds.

Weeds are undesirable plants growing where they are not wanted, having no economic value, and interfering with the production of cultivated crops, with the growing of ornamental plants, or with the welfare of livestock. Many types of weeds are known, including annuals such as pigweed, lambsquarters, foxtail, crabgrass, wild mustard, field pennycress, ryegrass, goose grass, chickweed, wild oats, velvetleaf, purslane, barnyardgrass, smartweed, knotweed, cocklebur, wild buckwheat, kochia, medic, corn cockle, ragweed, sowthistle, coffeeweed, croton, cuphea, dodder, fumitory, groundsel, hemp nettle, knawel, spurge, spurry, emex, jungle rice, pondweed, dog fennel, carpetweed, morningglory, bedstraw, ducksalad, naiad, cheatgrass, fall panicum, jimsonweed, witchgrass, switchgrass, watergrass, teaweed, wild turnip and sprangletop; biennials such as wild carrot, matricaria, wild barley, campion, chamomile, burdock, mullein, roundleaved mallow, bull thistle, hounds-tongue, moth mullein and purple star thistle; or perennials such as white cockle, perennial ryegrass, quackgrass, Johnsongrass, Canada thistle, hedge bindweed, Bermuda grass, sheep sorrel, curly dock, nutgrass, field chickweed, dandelion, campanula, field bindweed, Russian knapweed, mesquite, toadflax, yarrow, aster, gromwell, horsetail, ironweed, sesbania, bulrush, cattail, winter-cress, horsenettle, nutsedge, milkweed and sicklepod.

Similarly, such weeds can be classified as broadleaf or grassy weeds. It is economically desirable to control the growth of such weeds without damaging beneficial plants or livestock.

The new compounds of this invention are particularly valuable for weed control because they are toxic to many species and groups of weeds. The exact amount of compound required will depend on a variety of factors, including the hardiness of the particular weed species, weather, type of soil, method of application, the kind of beneficial plants in the same area and the like. Thus, while the application of up to only about 1 or 2 ounces of active compound per acre may be sufficient for good control of a light infestation of weeds growing under adverse conditions, the application of ten pounds or more of an active compound per acre may be required for good control of a dense infestation of hardy perennial weeds growing under favorable conditions.

The herbicidal toxicity of the new compounds of this invention can be illustrated by many of the established testing techniques known to the art, such as pre- and post-emergence testing.

The herbicidal activity of the compounds of this invention was demonstrated by experiments carried out for the pre-emergence control of a variety of weeds. In these experiments small plastic greenhouse pots filled with dry soil were seeded with the various weed seeds. Twenty-four hours or less after seeding the pots were sprayed with water until the soil was wet and the test compounds formulated as aqueous emulsions of acetone solutions containing emulsifiers were sprayed at the indicated concentrations on the surface of the soil.

After spraying, the soil containers were placed in the greenhouse and provided with supplementary heat as required and daily or more frequent watering. The plants were maintained under these conditions for a period of 21 days, at which time the condition of the plants and the degree of injury to the plants was rated on a scale of from 0 to 10, as follows: 0 = no injury, 1,2 = slight injury, 3,4 = moderate injury, 5,6 = moderately severe injury, 7,8,9 = severe injury and 10 = death. The effectiveness of these compounds is demonstrated by the data in Table I. Weed Species Test Rate Compound (lbs/acre) YNSG WOAT JMWD VTLF JNGS PIGW WMSTD YLFX BNGS CBGS CTGS MNGY BDWD SPGT QKGS WCANE YRFX Product of 2 -- 0 60 0 00 3 6 5 7 0 0 3 2 Example 2 1 -- 0 0 0 7 0 10 2 0 3 6 0 0 8 0 0.5 -- 0 0 2 0 0 0 0 0 3 0 0 0 0 4 Product of 8 4 5 3 4 9 10 0 8 10 10 10 0 -- -- -- Example 6 2 0 3 0 1 2 10 0 0 0 0 0 0 -- -- -- 1 0 0 0 0 0 10 0 0 0 0 0 0 -- -- -- Product of 8 8 0 0 2 5 6 4 6 10 9 7 5 -- -- -- Example 8 2 2 0 0 0 130252 00---- --12 0 0 0 0 0 0 2 0 0 0 0 -- -- -- Product of 8 9 0 0 5 9 9 0 9 9 10 3 4 -- -- -- Example 10 2 9 0 0 0 2 7 0 4 4 2 0 0 -- -- -- 1 0 0 0 0 0 10 0 1 2 2 0 0 -- -- -- Product of 8 6 4 4 5 5 10 5 6 10 9 8 0 -- -- -- Example 12 2 0 2 1 2 0 7 2 3 9 6 0 0 -- -- -- 1 0 0 0 0 0 0 0 0 5 0 0 0 -- -- -- Product of 8 10 0 0 0 5 9 4 6 7 10 10 0 -- -- -- Example 14 2 0 0 0 0 1 0 0 0 2 10 4 0 -- -- -- 1 0 0 0 0 0 0 0 0 0 4 0 0 -- -- -- Product of 8 2 2 0 1 4 2 3 9 9 5 2 4 -- -- -- -- -- Example 17 2 0 0 0 0 0 0 1 5 2 2 1 2 -- -- -- -- -- 1 0 0 0 0 0 0 1 2 0 0 0 1 -- -- -- -- -- Product of 8 10 2 0 2 10 9 0 9 10 9 9 4 -- -- -- -- -- Example 19 2 0 0 0 0 0 0 0 0 0 0 0 0 -- -- -- -- -- 1 0 0 0 0 0 0 0 0 0 0 0 0 -- -- -- -- -- Product of 8 9 6 0 5 9 8 7 9 10 9 10 2 -- -- -- -- -- Example 22 2 9 4 6 6 8* 8 1 8* 10* 7* 10 0 -- 10 -- 9 9 1 9 3 0 0 4.5* 8 3 5.5* 9* 5.5* 10* 2 3 9 8 2 8 0.5 -- -- -- -- 0 -- -- 3 10 6 5 -- 0 6 7 0 2 0.25 -- -- ---- 0 -- -- 4 4 4 0 -- 0 0 5 0 0 Product of 8 9 6 2 4 9 8 0 9 9 8 2 -- -- -- -- -- Example 23 2 9 1 1 2 0 3 0 8 9 5 3 3 -- -- -- -- -- 1 8 0 0 0 0 3 0 3 7 0 0 3 -- -- -- -- -- YNSG = Yellow Nutsedge WOAT = Wild Oats JMWD = Jimsonweed VTLF = Velvetleaf JNGS = Johnsongrass WCANE = Wild Cane PIGW = Pigweed WMSTD = Wild Mustard YLFX = Yellow Foxtail BNGS = Barnyardgrass CBGS = Crabgrass GRFX = Green Foxtail CTGS = Cheatgrass MNGY = Wild Morningglory BDWD = Bindweed SPGT = Sprangletop QKGS = Quackgrass *Ratings are averages of two tests.

The herbicidal activity of the compounds of this invention was also demonstrated by experiments carried out for the post-emergence control of a variety of weeds. In these experiments the compounds to be tested were formulated as aqueous emulsions and sprayed at the indicated dosage on the foliage of the weeds that have attained a prescribed size. After spraying, the plants were placed in a greenhouse and watered daily or more frequently. Water was not applied to the foliage of the treated plants. The severity of the injury was determined 14 days after treatment and was rated on the scale of from 0 to 10 heretofore described. The effectiveness of these compounds is demonstrated by the data in Table II. Weed Species Test Rate Compound (lbs/acre) YNSG WOAT JMWD VTLF JNGS PIGW WMSTD YLFX BNGS CBGS CTGS MNGY BDWD SPGT OKGS Product of 2 6 5 0 -- 8 4 0 7 6 5 -- 3 2 -- -- Example 2 1 3 4 0 -- 4 2 0 6 6 5 -- 0 3 -- -- 0.5 0 5* 1* 2 3.5* 0* 0* 4.5* 7* 5.5* 3 0 1* 5 5 0.25 -- 2 1 0 3 0 0 4 3 3 2 -- 0 3 4 0.125 -- 0 0 0 3 0 0 3 6 2 1 -- 0 1 2 Product of Example 6 8 0 4 0 -- 3 0 0 5 5 5 -- 2 0 -- -- 2 0 1 0 -- 1 0 0 4 4 3 -- 0 0 -- -- 1 0 3.5* 0* 0 2.5* 1.5* 0* 3.5* 5.5* 2 0 0* 6 6 0.5 -- 5 0 0 0 2 0 5 7 6 1 -- 0 6 2 0.25 -- 3 0 0 0 2 0 2 4 4 0 -- 0 3 4 Product of 8 4 5 3 -- 4 6 8 8 6 6 -- 4 2 -- -- Example 82540-- 020566-- 00----16 4* .5* 0 0* 3* 0* 5.5* 5.5* 6* 1 0 2.5* 6 4 0.5 -- 3 0 0 0 2 0 5 7 5 0 -- 2 7 4 0.25 -- 1 0 0 0 0 0 3 5 5 0 -- 0 3 3 Product of 8 2 5 2 -- 4 3 4 7 5 5 -- 1 0 -- -- Example 10 2 3 2 0 -- 0 2 2 7 5 4 -- 0 0 -- -- 1 4 2.5* 0* 0 3* 2.5* 0* 4* 5* 2.5* 2 0 0* 5 4 0.5 -- 3 0 0 3 3 0 0 6 2 2 -- 0 3 3 0.25 -- 2 0 0 2 3 0 0 1 0 0 -- 0 1 0 Product of 8 0 3 0 -- 4 1 2 4 4 3 -- 2 0 -- -- Example 12 2 0 0 0 -- 0 0 1 2 4 2 -- 0 0 -- -- 1 0 0 0 -- 0 0 0 2 4 0 -- 0 0 -- -- Product of 8 4 5 5 -- 5 3 10 7 6 6 -- 4 3 -- -- Example 14 2 2 2 0 -- 2 2 0 5 2 3 -- 2 0 -- -- 1 0 0 0 -- 0 0 0 1 0 1 -- 0 0 -- -- Product of 8 4 5 2 -- 4 8 3 7 7 6 -- 3 4 -- -- Example 17 2 4 3 0 -- 0 4 2 6 5 4 -- 0 0 -- -- 1 5 1 0 -- 0 0 0 5 5 0 -- 0 0 -- -- Product of 8 -- 5 3 -- 6 8 0 5 5 5 -- 4 3 -- -- Example 19 2 -- 4 0 -- 3 2 0 5 6 6 -- 2 0 -- -- 1 -- 3.5* 0* 0 1* 3* 1* 5.5* 6* 5.5* 4 0 1.5* 5 5 0.5 -- 3 0 0 0 4 0 6 7 5 2 -- 1 5 4 0.25 -- 3 0 0 0 2 0 1 5 4 0 -- 0 3 3 Product of 1 -- 5 3 0 4 6 0 6 6 5 3 -- -- 5 4 Example 22 0.5 -- 3 0 0 3 0 0 5 6 4 1 -- -- 5 4 0.25 -- 4 0 0 4 0 0 5 5 5 0 -- -- 4 3 Product of 8 3 7 4 -- 4 4 2 5 6 5 -- 5 4 -- -- Example 23 2 2 3 0 -- 4 0 0 7 7 6 -- 3 2 -- -- 1 2 2 0 -- 0 0 0 4 6 4 -- 2 2 -- -- YNSG = Yellow Nutsedge WOAT = Wild Oats JMWD = Jimsonweed VTLF = Velvetleaf JNGS = Johnsongrass WCANE = Wild Cane PIGW = Pigweed WMSTD = Wild Mustard YLFX = Yellow Foxtail BNGS = Barnyardgrass CBGS = Crabgrass GRFX = Green Foxtail CTGS = Cheatgrass MNGY = Wild Morningglory BDWD = Bindweed SPGT = Sprangletop QKGS = Quackgrass *Ratings are averages of two tests.