CA1155127A - Carbamoyl sulfoxides useful as herbicides - Google Patents
Carbamoyl sulfoxides useful as herbicidesInfo
- Publication number
- CA1155127A CA1155127A CA000178814A CA178814A CA1155127A CA 1155127 A CA1155127 A CA 1155127A CA 000178814 A CA000178814 A CA 000178814A CA 178814 A CA178814 A CA 178814A CA 1155127 A CA1155127 A CA 1155127A
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- Prior art keywords
- set forth
- compound
- carbon atoms
- alkyl
- taken together
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/21—Radicals derived from sulfur analogues of carbonic acid
Abstract
IN THE UNITED STATES PATENT OFFICE
HERBICIDE COMPOSITIONS
Abstract of the Disclosure Herbicidal active sulfoxide and sulfone compounds and their method of use are described herein. The compounds have the following generic formula:
HERBICIDE COMPOSITIONS
Abstract of the Disclosure Herbicidal active sulfoxide and sulfone compounds and their method of use are described herein. The compounds have the following generic formula:
Description
ll~S12~
Description of the Invention This invention is directed to a novel group of compounds which may be generally described as sulfoxide and sulfone deriva-tives of thiocarbamates which are highly active herbicides. The compounds of the present invention are represented by the generic formula:
¦¦ ,Rl R-S(O) -C-N
wherein n is 1 or 2; R is selected from the group consisting of phenalkyl, alkylphenalkyl, halophenalkyl and haloalkylphenalkyl;
Rl and R2 taken together form a heterocyclic ring structure or lower alkyl having 1-6 carbon atoms substituted heterocyclic ring stFucture.
The above-noted compounds can be prepared by reacting an oxidizing agent such as peracetic acid or m-chloroperoxybenzoic acid with a thiocarbamate compound corresponding to the following formula:
¦¦ ~ Rl R-S-C-~I~
wherein R, Rl and R2 have been defined above. The reaction is carried out in the presence of a solvent such as chloroform, methylene chloride, benzene or toluene and at a reduced tempera-ture of from about -25C. to about 65C. ~he amount of oxidizing agent used must be at least one molar equivalent to form the sulfoxide derivative and at least two molar equivalents to form the sulfone derivatives.
.~
1155~27 The thiocarbamate compounds are known herbicides and their method of synthesis is known; see U.S. Patents 2,913,327,
Description of the Invention This invention is directed to a novel group of compounds which may be generally described as sulfoxide and sulfone deriva-tives of thiocarbamates which are highly active herbicides. The compounds of the present invention are represented by the generic formula:
¦¦ ,Rl R-S(O) -C-N
wherein n is 1 or 2; R is selected from the group consisting of phenalkyl, alkylphenalkyl, halophenalkyl and haloalkylphenalkyl;
Rl and R2 taken together form a heterocyclic ring structure or lower alkyl having 1-6 carbon atoms substituted heterocyclic ring stFucture.
The above-noted compounds can be prepared by reacting an oxidizing agent such as peracetic acid or m-chloroperoxybenzoic acid with a thiocarbamate compound corresponding to the following formula:
¦¦ ~ Rl R-S-C-~I~
wherein R, Rl and R2 have been defined above. The reaction is carried out in the presence of a solvent such as chloroform, methylene chloride, benzene or toluene and at a reduced tempera-ture of from about -25C. to about 65C. ~he amount of oxidizing agent used must be at least one molar equivalent to form the sulfoxide derivative and at least two molar equivalents to form the sulfone derivatives.
.~
1155~27 The thiocarbamate compounds are known herbicides and their method of synthesis is known; see U.S. Patents 2,913,327,
2,983,747, 3,133,927, 3,175,897 and 3,185,720 for example. How-ever, the use of these thiocarbamates as reactive intermediates to form other compounds that also-have pesticidal activity is unexpected.
In order to illustrate the merits of the present inven-tion, the following examples are provided:
.
Example 1 ~ 2 4 ~CH - CH~ 2 In a 500 ml. 3-necked flask with thermometer, mechanice' stirrer and addition device were placed 100 ml. of methylene chlo--ide and 4.0 g. (0.014 mole) S-( ~ -phenylethyl)-1-(5-ethyl-2-methy~-piperidine) carbothioate dissolved in 25 ml. of methylene chlori~e~
Stirring was begun and the temperature lowered to -30C. with a dry ice bath. Then, 2.4 g. (0.014 mole) of m-chloroperoxybenzoic acid were added and the temperature held at -30C. for 15 minutes.
The temperature was allowed to reach 0C. in about 30 minutes.
Thereafter, the temperature was allowed to reach 4C., whereupon the mixture was filtered. The filtrate was washed with two 50 ..~1.
portions of 5% potassium carbonate and one 50 ml. portion of water, then dried over magnesium sulfate to yield 3,0 g. of pro-duct, nD - 1.5508.
li~yS12q Example 2 C2H4~ C-N ~ 2 = ~ CH2 A solution was formed containing 5.8 g. of m-chloro-peroxybenzoic acid in 100 ml. of methylene chloride at room tem-perature. The solution was then warmed to 30C. and 4.9 g.
(0.017 mole) of S-(~ -phenylethyl)-1-(5~ethyl-2-methylpiperidine) carbothioate in 25 ml. of methylene chloride were added at a rate such that gentle reflux was maintained. The solution was stirred at reflux for 30 minutes, then cooled to 5C. in an ice bath. The solid was filtered off an~ washed with cold methylene chloride.
The combined filtrate portions were washed with three 50 ml. por-tions of 5% potassium carbonate, two 50 ml. portions of water, then dried over magnesium sulfate and str~pped to yield 5.6 g. of product, nD - 1.5384.
Other compounds were prepared in an analogous manner starting with the appropriate starting materials as outlined above. The following is a table of compounds representative of those embodied by the present invention. Compound numbers have been assigned to them and are used for identification throughout the balance of the specification.
:115SlZ7 TABLE I
R
Compound Number R Rl R2 n Cl 2H5 C2 4~ CH2--CH
2 -CH2~ CH2-CH2-CH2
In order to illustrate the merits of the present inven-tion, the following examples are provided:
.
Example 1 ~ 2 4 ~CH - CH~ 2 In a 500 ml. 3-necked flask with thermometer, mechanice' stirrer and addition device were placed 100 ml. of methylene chlo--ide and 4.0 g. (0.014 mole) S-( ~ -phenylethyl)-1-(5-ethyl-2-methy~-piperidine) carbothioate dissolved in 25 ml. of methylene chlori~e~
Stirring was begun and the temperature lowered to -30C. with a dry ice bath. Then, 2.4 g. (0.014 mole) of m-chloroperoxybenzoic acid were added and the temperature held at -30C. for 15 minutes.
The temperature was allowed to reach 0C. in about 30 minutes.
Thereafter, the temperature was allowed to reach 4C., whereupon the mixture was filtered. The filtrate was washed with two 50 ..~1.
portions of 5% potassium carbonate and one 50 ml. portion of water, then dried over magnesium sulfate to yield 3,0 g. of pro-duct, nD - 1.5508.
li~yS12q Example 2 C2H4~ C-N ~ 2 = ~ CH2 A solution was formed containing 5.8 g. of m-chloro-peroxybenzoic acid in 100 ml. of methylene chloride at room tem-perature. The solution was then warmed to 30C. and 4.9 g.
(0.017 mole) of S-(~ -phenylethyl)-1-(5~ethyl-2-methylpiperidine) carbothioate in 25 ml. of methylene chloride were added at a rate such that gentle reflux was maintained. The solution was stirred at reflux for 30 minutes, then cooled to 5C. in an ice bath. The solid was filtered off an~ washed with cold methylene chloride.
The combined filtrate portions were washed with three 50 ml. por-tions of 5% potassium carbonate, two 50 ml. portions of water, then dried over magnesium sulfate and str~pped to yield 5.6 g. of product, nD - 1.5384.
Other compounds were prepared in an analogous manner starting with the appropriate starting materials as outlined above. The following is a table of compounds representative of those embodied by the present invention. Compound numbers have been assigned to them and are used for identification throughout the balance of the specification.
:115SlZ7 TABLE I
R
Compound Number R Rl R2 n Cl 2H5 C2 4~ CH2--CH
2 -CH2~ CH2-CH2-CH2
3 -CH2~ Cl ~CH2-CH2-CIH2
4 -C2H4~ CH2--bH 2 bH ~ ~`
-CH2~H3 CH2-C~2-CIH2 6 -CH2--~3Cl CU2--CH2 11551:Z7 Compound Number R Rl R2 n 7 -CH2~CH3 ~ CH2--CH2 8 -CH2~Cl CH2--CH
Cl 2H5 9-CH2 e}cH3 --CH--CH2 2 C~ 2H5 10 -CH2~CF3 --CH--CH2 2 Cl 11 -CH2~ CH2-CH2-ClH2 'F/ --CH2-CH2-CH2 Cl 12 -CH ~9 CH2-CH2-CH2 2 ~ .~ CH2-CH2-CH2 llSS~2~
Compound _Number R Rl --2 13 -CH2-~Cl ~CH2--CH2 14 -CH2~Cl CH2--CH
-CH2~Cl --CH~CH2~ 3 16 -CH2 0 Cl~ CH--CH2~ 2 17 -CH ~ Cl .~ CH2--CH2 18 -CH2~Cl /C\--CH2 1$~27 Compound Number R Rl R2 n l 2H5 19 -CH2 ~ ,,_CH2--CH
Herbicidal Screening Tests As previously mentioned, the novel compounds herein described are phytotoxic compounds which are useful and valuable in controlling various plant species. Compounds of this inventlon are tested as herbicides in the following manner.
Pre-emer~ence Herbicide Screenin~ Test Using an analytical balance, 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 bott'e and 3 ml. of acetone containing 1% Tween 20 ~ is added to dis-solve the compound, If the material is not soluble in acetone, another solvent such as water, alcohol or dimethylformamide (D~F) 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 styrofoam flat one day after planting weed seeds in the flat of soil, A No, 152 DeVilbiss 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 gal./acre.
~,lSS~27 On the day preceding treatment, the styrofoam flat which is 7 inchcs 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 ar~
covered with soil so that they are planted at a depth of 0.5 inch.
The seeds used are hairy crabgrass (Di~it~ria san~uinalis), yello~
foxtail (Setaria ~lauca), watergrass (Echinochloa crus~alli), red oat (Avena sativa), redroot pigweed (Amaranthus retroflexus), Indian mustard (Brassica juncea) and curly dock (Rumex crispus~.
Ample seeds are planted to give about 20 to 50 seedlings per row after emergence depending on the size of the plants.
After treatment, the flats are placed in the greenhouse at a temperature of 70 to 85F. and watered by sprinkling. Two weeks after treatment, the degree of injury or control is deter-mined 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 0% representing no injury and 10~/o repre-senting complete kill.
Post-emer~ence Herbicide Screenin~ Test Seeds of six plant species, including hairy crabgrass, watergrass, red oat, mustard, curly dock and Pinto bean (Phaseolus w lgaris) are planted in the styrofoam flats as described above for pre-emergence screening. The flats are placed in the green-house at 70-85F. and watered daily with a sprinkler. About 13 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 ia prepared by weighing out 20 mg of the test compound, dissolving llSS~
it in S ml. of acetone contalning 1% Tween 20 ~ and then ~dding
-CH2~H3 CH2-C~2-CIH2 6 -CH2--~3Cl CU2--CH2 11551:Z7 Compound Number R Rl R2 n 7 -CH2~CH3 ~ CH2--CH2 8 -CH2~Cl CH2--CH
Cl 2H5 9-CH2 e}cH3 --CH--CH2 2 C~ 2H5 10 -CH2~CF3 --CH--CH2 2 Cl 11 -CH2~ CH2-CH2-ClH2 'F/ --CH2-CH2-CH2 Cl 12 -CH ~9 CH2-CH2-CH2 2 ~ .~ CH2-CH2-CH2 llSS~2~
Compound _Number R Rl --2 13 -CH2-~Cl ~CH2--CH2 14 -CH2~Cl CH2--CH
-CH2~Cl --CH~CH2~ 3 16 -CH2 0 Cl~ CH--CH2~ 2 17 -CH ~ Cl .~ CH2--CH2 18 -CH2~Cl /C\--CH2 1$~27 Compound Number R Rl R2 n l 2H5 19 -CH2 ~ ,,_CH2--CH
Herbicidal Screening Tests As previously mentioned, the novel compounds herein described are phytotoxic compounds which are useful and valuable in controlling various plant species. Compounds of this inventlon are tested as herbicides in the following manner.
Pre-emer~ence Herbicide Screenin~ Test Using an analytical balance, 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 bott'e and 3 ml. of acetone containing 1% Tween 20 ~ is added to dis-solve the compound, If the material is not soluble in acetone, another solvent such as water, alcohol or dimethylformamide (D~F) 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 styrofoam flat one day after planting weed seeds in the flat of soil, A No, 152 DeVilbiss 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 gal./acre.
~,lSS~27 On the day preceding treatment, the styrofoam flat which is 7 inchcs 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 ar~
covered with soil so that they are planted at a depth of 0.5 inch.
The seeds used are hairy crabgrass (Di~it~ria san~uinalis), yello~
foxtail (Setaria ~lauca), watergrass (Echinochloa crus~alli), red oat (Avena sativa), redroot pigweed (Amaranthus retroflexus), Indian mustard (Brassica juncea) and curly dock (Rumex crispus~.
Ample seeds are planted to give about 20 to 50 seedlings per row after emergence depending on the size of the plants.
After treatment, the flats are placed in the greenhouse at a temperature of 70 to 85F. and watered by sprinkling. Two weeks after treatment, the degree of injury or control is deter-mined 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 0% representing no injury and 10~/o repre-senting complete kill.
Post-emer~ence Herbicide Screenin~ Test Seeds of six plant species, including hairy crabgrass, watergrass, red oat, mustard, curly dock and Pinto bean (Phaseolus w lgaris) are planted in the styrofoam flats as described above for pre-emergence screening. The flats are placed in the green-house at 70-85F. and watered daily with a sprinkler. About 13 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 ia prepared by weighing out 20 mg of the test compound, dissolving llSS~
it in S ml. of acetone contalning 1% Tween 20 ~ and then ~dding
5 ml. of w~ter. The solution is sprayed on the foli~ge using 2 No. 152 DeVilbiss atomizer at an air pressure of 5 lb./sq. inch.
The spray concentration is 0.2 and the rate 1s 8 lb./acre. The spray volume is 476 gal./acre. Injury ratings are recorded 14 days after treatment. The rating system is the same as described above for the pre-emergence test.
The results of these tests are shown in Table II, TABLE II
HERBICIDAL ACTIVITY - SCREENING RESULTS
Compound Number Pre-emergence Post-emer~ence
The spray concentration is 0.2 and the rate 1s 8 lb./acre. The spray volume is 476 gal./acre. Injury ratings are recorded 14 days after treatment. The rating system is the same as described above for the pre-emergence test.
The results of these tests are shown in Table II, TABLE II
HERBICIDAL ACTIVITY - SCREENING RESULTS
Compound Number Pre-emergence Post-emer~ence
6 29 50
7 27 55 ''`
14 62 ~ 53 llSS~2~
TABLE TI (Cont.) Per Cent Control at 20 lb /A
Compound Number Pre-emer~ence Post~emer~ence
14 62 ~ 53 llSS~2~
TABLE TI (Cont.) Per Cent Control at 20 lb /A
Compound Number Pre-emer~ence Post~emer~ence
8 0 8 The compounds of the present invention can be used in any convenient form. Thus, the compounds can be made into emul-sifiable liquids, emulsifiable concentrates, liquid, wettable powder, powders, granular or any other convenient form, and applied to the soil to control the undesired vegetation.
.The heterocyclic ring structure can have from 3 to 10 carbon atoms, preferably from 4 to 6 carbon atoms.
.The heterocyclic ring structure can have from 3 to 10 carbon atoms, preferably from 4 to 6 carbon atoms.
Claims (44)
1. A compound represented by the following generic formula:
wherein n is 1 or 2; R is selected from the group consisting of phenalkyl wherein the alkyl group contains 1 to 4 carbon atoms, alkylphenalkyl wherein the alkyl group contain 1 to 4 carbon atoms, halophenalkyl wherein the alkyl group contains 1 to 4 carbon atoms, and haloalkylphenalkyl wherein the alkyl groups contain 1 to 4 carbon atoms; R1 and R2 taken together form an alkylene group containing from 4 to 6 carbon atoms or an alkylene group containing 4 to 6 carbon atoms substituted with lower alkyl.
wherein n is 1 or 2; R is selected from the group consisting of phenalkyl wherein the alkyl group contains 1 to 4 carbon atoms, alkylphenalkyl wherein the alkyl group contain 1 to 4 carbon atoms, halophenalkyl wherein the alkyl group contains 1 to 4 carbon atoms, and haloalkylphenalkyl wherein the alkyl groups contain 1 to 4 carbon atoms; R1 and R2 taken together form an alkylene group containing from 4 to 6 carbon atoms or an alkylene group containing 4 to 6 carbon atoms substituted with lower alkyl.
2. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 1.
3. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 1.
4. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 1.
5. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 2.
6. The compound as set forth in Claim 1 wherein R is , Rl and R2 are and n is 1.
7. The compound as set forth in Claim l wherein R is , Rl and R2 are and n is 1.
8. The compound as set forth in Claim 1 wherein R is , Rl and R2 are and n is 1.
9. The compound as set forth in Claim 1 wherein R is , Rl and R2 are and n is 1.
10. The compound as set forth in Claim 1 wherein R is , Rl and R2 are and n is 1.
11. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 1.
12. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 1.
13. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 1.
14. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 1.
15. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 1.
16. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 1.
17. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 1.
18. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 1.
19. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 1.
20. The compound as set forth in Claim 1 wherein R is , R1 and R2 are and n is 1.
21. The method of controlling undesirable vegetation comprising applying to the locus where control is desired an herbicidally effective amount of a compound represented by the following formula:
wherein n is 1 or 2; R is selected from the group consisting of phenalkyl wherein the alkyl group contains 1 to 4 carbon atoms, alkylphenalkyl wherein the alkyl groups contain 1 to 4 carbon atoms, halophenalkyl wherein the alkyl group contains 1 to 4 carbon atoms, and haloalkylphenalkyl wherein the alkyl groups contain 1 to 4 carbon atoms; R1 and R2 taken together form an alkylene group containing from 4 to 6 carbon atoms or an alkylene group containing 4 to 6 carbon atoms substituted with lower alkyl.
wherein n is 1 or 2; R is selected from the group consisting of phenalkyl wherein the alkyl group contains 1 to 4 carbon atoms, alkylphenalkyl wherein the alkyl groups contain 1 to 4 carbon atoms, halophenalkyl wherein the alkyl group contains 1 to 4 carbon atoms, and haloalkylphenalkyl wherein the alkyl groups contain 1 to 4 carbon atoms; R1 and R2 taken together form an alkylene group containing from 4 to 6 carbon atoms or an alkylene group containing 4 to 6 carbon atoms substituted with lower alkyl.
22. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
23. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
24. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
25. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 2.
26. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
27. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
28. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
29. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
30. The method as set forth in Claim 21 wherein R is , R1 and R2 and n is 1.
31. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
32. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
33. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
34. The method as set forth in C1aim 21 wherein R is , R1 and R2 are and n is 1.
35. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
36. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
37. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
38. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
39. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
40. The method as set forth in Claim 21 wherein R is , R1 and R2 are and n is 1.
41. A process of manufacturing compounds having the formula:
wherein n is 1 or 2; R is selected from phenalkyl wherein the alkyl group contains 1 to 4 carbon atoms, alkylphenalkyl wherein the alkyl groups contain 1 to 4 carbon atoms, halophenalkyl wherein the alkyl group contains 1 to 4 carbon atoms, and haloalkylphenalkyl wherein the alkyl groups contain 1 to 4 carbon atoms; R1 and R2 taken together form an alkylene group containing from 4 to 6 carbon atoms or an alkylene group containing 4 to 6 carbon atoms substituted with lower alkyl, comprising the steps of:
(a) reacting an oxidizing agent and a thiocarbamate compound, said thiocarbamate compound having the formula:
wherein R, R1 and R2 have been defined previously;
(b) said reaction being carried out at a temperature of between -25°C. and 65°C.;
(c) said oxidizing agent being selected from the group consisting of paracetic acid and m-chloroperoxybenzoic acid and being present in an amount of at least one molar equivalent.
wherein n is 1 or 2; R is selected from phenalkyl wherein the alkyl group contains 1 to 4 carbon atoms, alkylphenalkyl wherein the alkyl groups contain 1 to 4 carbon atoms, halophenalkyl wherein the alkyl group contains 1 to 4 carbon atoms, and haloalkylphenalkyl wherein the alkyl groups contain 1 to 4 carbon atoms; R1 and R2 taken together form an alkylene group containing from 4 to 6 carbon atoms or an alkylene group containing 4 to 6 carbon atoms substituted with lower alkyl, comprising the steps of:
(a) reacting an oxidizing agent and a thiocarbamate compound, said thiocarbamate compound having the formula:
wherein R, R1 and R2 have been defined previously;
(b) said reaction being carried out at a temperature of between -25°C. and 65°C.;
(c) said oxidizing agent being selected from the group consisting of paracetic acid and m-chloroperoxybenzoic acid and being present in an amount of at least one molar equivalent.
42. The process of Claim 41 wherein the oxidizing agent is m-chloroperoxybenzoic acid.
43 Compounds of the class of carbamoyl sulphoxides having the general formula:
wherein Ra is selected from:
- hydrogen;
- alkyl containing 1 to 4 carbon atoms; and - halogen;
and wherein Rl and R2 taken together represent alkylene contain-ing 4 to 6 carbon atoms.
wherein Ra is selected from:
- hydrogen;
- alkyl containing 1 to 4 carbon atoms; and - halogen;
and wherein Rl and R2 taken together represent alkylene contain-ing 4 to 6 carbon atoms.
44 A process for manufacturing a compound having the general formula:
wherein Ra is selected from:
- hydrogen;
- alkyl containing 1 to 4 carbon atoms; and - halogen;
and wherein R1 and R2 taken together represent alkylene containing 4 to 6 carbon atoms comprising the steps of:
(a) reacting an oxidizing agent selected from:
(i) peracetic acid; and (ii) m-chloroperoxybenzoic acid with a thiocarbamate, said thiocarbamate hav-ing the general formula:
wherein Ra, R1 and R2 have been previously defined;
(b) said reaction being carried out at a temperature between -25°C and 50°C; and (c) said oxidizing agent being present in an amount of one molar equivalent.
A method of controlling undesirable vegetation compris-ing applying to the locus where the control is desired an effective amount of a compound represented by the general formula:
wherein Ra is selected from:
- hydrogen;
- alkyl containing 1 to 4 carbon atoms; and - halogen;
and wherein R1 and R2 taken together represent alkylene contain-ing 4 to 6 carbon atoms.
wherein Ra is selected from:
- hydrogen;
- alkyl containing 1 to 4 carbon atoms; and - halogen;
and wherein R1 and R2 taken together represent alkylene containing 4 to 6 carbon atoms comprising the steps of:
(a) reacting an oxidizing agent selected from:
(i) peracetic acid; and (ii) m-chloroperoxybenzoic acid with a thiocarbamate, said thiocarbamate hav-ing the general formula:
wherein Ra, R1 and R2 have been previously defined;
(b) said reaction being carried out at a temperature between -25°C and 50°C; and (c) said oxidizing agent being present in an amount of one molar equivalent.
A method of controlling undesirable vegetation compris-ing applying to the locus where the control is desired an effective amount of a compound represented by the general formula:
wherein Ra is selected from:
- hydrogen;
- alkyl containing 1 to 4 carbon atoms; and - halogen;
and wherein R1 and R2 taken together represent alkylene contain-ing 4 to 6 carbon atoms.
Applications Claiming Priority (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28037472A | 1972-08-14 | 1972-08-14 | |
| US28038672A | 1972-08-14 | 1972-08-14 | |
| US28037572A | 1972-08-14 | 1972-08-14 | |
| US280,386 | 1972-08-14 | ||
| US280,374 | 1972-08-14 | ||
| US280,375 | 1972-08-14 | ||
| US37109273A | 1973-06-18 | 1973-06-18 | |
| US37102873A | 1973-06-18 | 1973-06-18 | |
| US37109373A | 1973-06-18 | 1973-06-18 | |
| US371,092 | 1973-06-18 | ||
| US371,093 | 1973-06-18 | ||
| US371,028 | 1973-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1155127A true CA1155127A (en) | 1983-10-11 |
Family
ID=27559548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000178814A Expired CA1155127A (en) | 1972-08-14 | 1973-08-14 | Carbamoyl sulfoxides useful as herbicides |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5612606B2 (en) |
| CA (1) | CA1155127A (en) |
| FR (1) | FR2196122B1 (en) |
| GB (1) | GB1382968A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58171406U (en) * | 1982-05-12 | 1983-11-16 | 成「沢」 恒夫 | Water stop plate for jointing |
| JPS598410U (en) * | 1982-07-09 | 1984-01-19 | 一枚田 忠雄 | Water stop device for concrete frame joints |
| JPS59124122U (en) * | 1983-02-10 | 1984-08-21 | 日瀝化学工業株式会社 | joint board |
-
1973
- 1973-08-14 GB GB3950273A patent/GB1382968A/en not_active Expired
- 1973-08-14 FR FR7329773A patent/FR2196122B1/fr not_active Expired
- 1973-08-14 CA CA000178814A patent/CA1155127A/en not_active Expired
- 1973-08-14 JP JP9125173A patent/JPS5612606B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS49124226A (en) | 1974-11-28 |
| FR2196122A1 (en) | 1974-03-15 |
| FR2196122B1 (en) | 1977-08-12 |
| GB1382968A (en) | 1975-02-05 |
| JPS5612606B2 (en) | 1981-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |