CA1155126A - Herbicide compositions - Google Patents
Herbicide compositionsInfo
- Publication number
- CA1155126A CA1155126A CA000178802A CA178802A CA1155126A CA 1155126 A CA1155126 A CA 1155126A CA 000178802 A CA000178802 A CA 000178802A CA 178802 A CA178802 A CA 178802A CA 1155126 A CA1155126 A CA 1155126A
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- Canada
- Prior art keywords
- set forth
- compound
- carbon atoms
- taken together
- lower alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
IN THE UNITED STATES PATENT OFFICE
HERBICIDE COMPOSITIONS
Abstract of the Disclosure Herbicidal active sulfoxide and sulfone compounds are described herein. The compounds have the following generic formula:
wherein n is 1 or 2; R is selected from the group consisting of lower alkyl and haloalkyl;
Rl and R2 taken together can form a heterocyclic ring structure having from 2 to 10 carbon atoms or alkyl substituted heterocyclic ring structure, The heterocyclic ring can be provided with cross-bonding.
HERBICIDE COMPOSITIONS
Abstract of the Disclosure Herbicidal active sulfoxide and sulfone compounds are described herein. The compounds have the following generic formula:
wherein n is 1 or 2; R is selected from the group consisting of lower alkyl and haloalkyl;
Rl and R2 taken together can form a heterocyclic ring structure having from 2 to 10 carbon atoms or alkyl substituted heterocyclic ring structure, The heterocyclic ring can be provided with cross-bonding.
Description
` ` 1~.5512~
escription 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:
o ¦¦ ~R
( )n C N R
wherein n is 1 or 2; R is selected from the group consisting of lower alkyl having 1 - 6 carbon atoms and halo-lower alkyl; Rl and R2 taken together can form an alkylene having 5 or 6 carbon atoms, alkyl having 1 to 4 carbon atoms substituted alkylene group having 5 or 6 carbon atoms, or / CH2 -- CH~
C~ C /CH2 ~C112--Cl~ci12 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:
o ¦¦ ~R
R-S-C-N
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 temperature of from about -25C. to about 60C. The 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.
4~
115StZ6 The thiocarbamate compounds are known herbicides and their method of synthesis is known; see U. S. Patents 2,913,327,
escription 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:
o ¦¦ ~R
( )n C N R
wherein n is 1 or 2; R is selected from the group consisting of lower alkyl having 1 - 6 carbon atoms and halo-lower alkyl; Rl and R2 taken together can form an alkylene having 5 or 6 carbon atoms, alkyl having 1 to 4 carbon atoms substituted alkylene group having 5 or 6 carbon atoms, or / CH2 -- CH~
C~ C /CH2 ~C112--Cl~ci12 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:
o ¦¦ ~R
R-S-C-N
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 temperature of from about -25C. to about 60C. The 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.
4~
115StZ6 The thiocarbamate compounds are known herbicides and their method of synthesis is known; see U. S. Patents 2,913,327,
2,983,747, 3,133,9475 3,175,897 and 3,185,720 for,example.---How-ever, the use of these ~hiocarbamates as reactive intermediates to form other compounds that also have pesticidal activity is unexpected.
In order to illustrate the merits of,the present in-vention the following examples are provided:
Example I
O O ~CH2-CH2-CH2 CH2-CH2-CH2 i A solution was formed containing 11.2 grams (0.055 mole) of m-chloroperoxybenzoic acid and 200 cc. of methylene chloride in a reaction vessel.' This solution was cooled in dry ice to -14C. wherein 9.4 grams (0.05 mole) of S-ethylhexahydro-lH-azepine-l-carbothioate was added over a per~od o~ four minutes wherein the temperature increased to -13C. The reaction mass was cooled to -14.5C. and allowed to fluctuate for about 1 hour wherein the reaction mass was cooled to -5C. Wherein the re-action mass was allowed to wa~m to 20C. The reaction mass was then cooled to 2.5C. wherein the mixture was filtered and the cake was washed with two portions of 25 cc. of methylene chlo-ride. The combined filtrate was washed with four portions of 100 cc. 5 percent sodium carbonate solution and two portions of lO0 cc. of water, dried over magnesium sulfate and concentrated in the rotary evaporator, first under water pump vacuum and finally under high vacuum to yield 9.1 grams of residual liquid.
This residual liquid was redistilled to yield 8.0 grams of product, n30 _ 1.5274.
Example II
O O ~CH2-CH2-CH2 C2H5-S-C-N ¦
A solution was formed containing 22.3 grams (0.11 mole) of m-chloroperoxybenzoic acid in 300 cc. of methylene chloride in a reaction vessel. This solution was warmed to 29.5C. wherein 9.4 grams of S-ethylhexahydro-lH-azepine-l-carbothioate was added over a period of three minutes. During thè addition the tèmper-ature rose to 41C. After 1.5 hours the solution was cooled to 9C. and was filtered with the cake being washed with two portions of ~5 cc. of methylene chloride. The filtrate was washed with four portions of 100 cc. 5% solution of sodium carbonate and two portions of 100 cc, of water, dried over magnesium sulfate ant concentrated in a rotary evaporator under water pump vacuum to yleld 10.3 grams of product, n30 _ 1.5000.
" ~ ~
Exam~le III
8 CH2 CH \
i-C3H7-S-C- ~ / CH2 A solution was formed containing 22.3 grams (0.11 mole) of m-chloroperoxybenzoic acid in 300 cc. methylene chloride. This solution was cooled to 30.5C. wherein 11.5 grams (0.05 mole) of S^isopropyl-5-ethyl-2-methylpiperidine-1-carbothioate was added over a period of 3 minutes. During the addition the temperature rose to 41.5C. The reaction was maintained at this temperature and then cooled in ice and filtered with the cake being washed with two portions of 25 cc. of methylene chloride and dried in the oven. The combined filtrate was washed with four portions of 100 cc. 5% solution sodium carbonate and two portions of 100 cc.
water, dried over magnesiumsulfate and concentrated in the rotary evaporator, first under water pump vacuum and finally under high vacuum to yield 12.2 grams of product, n30 _ 1.4871.
ample IV
/CH2-C~
C~ ~CH2 4 9 \ ~ 2 S A solution was formed containing 12.8 grams of S-butyl decahydroquinoline-l-carbothioate (0.05 mole) in 200 cc. of methyl-ene chloride. This solution was cooled to -14C. wherein 10.7 ` ~5S~26 grams (0~0525 mole) of m-chloroperoxybenzoic acid was added over a period of 5 minutes. The reaction mass was maintained at this temperature for a period of about 1 hour and 10 minutes, wherein it was warmed to -5C. and maintained at this tem~ rature for~
another 30 minutes. Thereafter, the reaction mass was allowed to wanm to 16C. wherein the mixture was filtered and the cake wash-ed with two portions of 25 cc. of methylene chloride. The ~om-. bined filtrate was washed with four portions of 100 cc. 5%
sodium carbonate solution and two portions~of i00 cc. water, dried over magne~hm sulfate and concentrated in a rotary evaporator, first under water pump vacuum and finally under high vacuum to yield 12.0 grams of product, n30 _ 1.5282.
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.
...
TABLE I
O ~R
R-S(O) -C-N
Compound Number R R and R n -C2H5 < ¦ 1 TABLE I . . . Continued . .
Compound Ntm~ber R Rl and Re n 2 - -C2H5 / ¦ 2 ~CH2-CH2
In order to illustrate the merits of,the present in-vention the following examples are provided:
Example I
O O ~CH2-CH2-CH2 CH2-CH2-CH2 i A solution was formed containing 11.2 grams (0.055 mole) of m-chloroperoxybenzoic acid and 200 cc. of methylene chloride in a reaction vessel.' This solution was cooled in dry ice to -14C. wherein 9.4 grams (0.05 mole) of S-ethylhexahydro-lH-azepine-l-carbothioate was added over a per~od o~ four minutes wherein the temperature increased to -13C. The reaction mass was cooled to -14.5C. and allowed to fluctuate for about 1 hour wherein the reaction mass was cooled to -5C. Wherein the re-action mass was allowed to wa~m to 20C. The reaction mass was then cooled to 2.5C. wherein the mixture was filtered and the cake was washed with two portions of 25 cc. of methylene chlo-ride. The combined filtrate was washed with four portions of 100 cc. 5 percent sodium carbonate solution and two portions of lO0 cc. of water, dried over magnesium sulfate and concentrated in the rotary evaporator, first under water pump vacuum and finally under high vacuum to yield 9.1 grams of residual liquid.
This residual liquid was redistilled to yield 8.0 grams of product, n30 _ 1.5274.
Example II
O O ~CH2-CH2-CH2 C2H5-S-C-N ¦
A solution was formed containing 22.3 grams (0.11 mole) of m-chloroperoxybenzoic acid in 300 cc. of methylene chloride in a reaction vessel. This solution was warmed to 29.5C. wherein 9.4 grams of S-ethylhexahydro-lH-azepine-l-carbothioate was added over a period of three minutes. During thè addition the tèmper-ature rose to 41C. After 1.5 hours the solution was cooled to 9C. and was filtered with the cake being washed with two portions of ~5 cc. of methylene chloride. The filtrate was washed with four portions of 100 cc. 5% solution of sodium carbonate and two portions of 100 cc, of water, dried over magnesium sulfate ant concentrated in a rotary evaporator under water pump vacuum to yleld 10.3 grams of product, n30 _ 1.5000.
" ~ ~
Exam~le III
8 CH2 CH \
i-C3H7-S-C- ~ / CH2 A solution was formed containing 22.3 grams (0.11 mole) of m-chloroperoxybenzoic acid in 300 cc. methylene chloride. This solution was cooled to 30.5C. wherein 11.5 grams (0.05 mole) of S^isopropyl-5-ethyl-2-methylpiperidine-1-carbothioate was added over a period of 3 minutes. During the addition the temperature rose to 41.5C. The reaction was maintained at this temperature and then cooled in ice and filtered with the cake being washed with two portions of 25 cc. of methylene chloride and dried in the oven. The combined filtrate was washed with four portions of 100 cc. 5% solution sodium carbonate and two portions of 100 cc.
water, dried over magnesiumsulfate and concentrated in the rotary evaporator, first under water pump vacuum and finally under high vacuum to yield 12.2 grams of product, n30 _ 1.4871.
ample IV
/CH2-C~
C~ ~CH2 4 9 \ ~ 2 S A solution was formed containing 12.8 grams of S-butyl decahydroquinoline-l-carbothioate (0.05 mole) in 200 cc. of methyl-ene chloride. This solution was cooled to -14C. wherein 10.7 ` ~5S~26 grams (0~0525 mole) of m-chloroperoxybenzoic acid was added over a period of 5 minutes. The reaction mass was maintained at this temperature for a period of about 1 hour and 10 minutes, wherein it was warmed to -5C. and maintained at this tem~ rature for~
another 30 minutes. Thereafter, the reaction mass was allowed to wanm to 16C. wherein the mixture was filtered and the cake wash-ed with two portions of 25 cc. of methylene chloride. The ~om-. bined filtrate was washed with four portions of 100 cc. 5%
sodium carbonate solution and two portions~of i00 cc. water, dried over magne~hm sulfate and concentrated in a rotary evaporator, first under water pump vacuum and finally under high vacuum to yield 12.0 grams of product, n30 _ 1.5282.
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.
...
TABLE I
O ~R
R-S(O) -C-N
Compound Number R R and R n -C2H5 < ¦ 1 TABLE I . . . Continued . .
Compound Ntm~ber R Rl and Re n 2 - -C2H5 / ¦ 2 ~CH2-CH2
3 n-C3H7 ~ /CH2 .
4 n C3H7 ~ ~:H2 2 . 2 2 HS
~CH2 C~
S i C3H7 \ ~CH2 . /CH2 C~
6 i-C3H7 \ /CH2 2 ~CH2-CH
7 C3H6 Cl \ ~CH2 115~
TABLE I . . . Con t inued Compound Number R Rl and R2 n CH" -CH
8 C3H6 ClCIH--CH2 2 2 9 n-C4H9 2--CH---CH-- 2 '--CH2 -C~ H2 CH -CH -CH
-i-C H~ 2 2 1 2 3 7~ CH2 -CH2 -CH2 12 -n-C H 2 CH
3 7~ CH--CH2-- 2 13 -n-C3H7CH2-CH2-JCH2 14 -n-C4HgCH2-CH2-CIH2 ~i~C4HgCH2-CH2-fH2 lSS5~Z6 TABLE I...Continued Compound N~nnber R R and R n Cl 2H5 16 n C3H6 Cl --CH--CF~CH2 CH2-CH ~' 17 -C2H5 =C~CH~ H2 ,,b2H5 Cl 2H5 18 -CH3~CI H--CH2 2 Cl 2H5 ~CH,~ ~CH
19 -C2H5~ ICH--CH2 2 .CH2-CH
-n-C3H7--CH--CH2 2 ~H3 C~ 2H5 21 -n-C4H9 ~ CH--CH-- H2 TABLE I...Continued Compound Number R Rand R n ~2H5 22 -i-C4Hg CH2-CH
23 -sec-c4H9 - CH- CH - H2 Herbicidal Screenin~ Tests As previously mentioned, the novel compounds herein described are phytotoxic compounds which are useful and valuable in controlling various plants species. Compounds of this inven-tion are tested as herbicides in the following manner.
A. Preemer~ence Herbicide Screenin~ Test: Using an analyti-cal balance, 20 mg of the compound to be tested i8 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 con-taining l~/o Tween 20 ~ is added to dissolve the compound. If the material is not soluble in acetone, another solvent such as water, alcohol or dimethylformamide (DMF) is used instead. When DMF is used, only 0.5 ml or less is uæed to dissolve the compound and llSS~Z6 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 ~t a pressure of 5 lb/sq.in. The rate of application is 8 lb/acre and the spray volume is 143 gal/acre.
On the day preceding treatment, the Styrofoam 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. The seeds used are hairy crabgrass (Di~itaria sanguinalis), yellow foxtail (Setaria ~lauca), watergrass ( chinochl-oa crusgalli), red oat (Avena sativa), redroot pigweed (Amaranthus retroflexus), Indian mustard (Brassica ~uncea) and curly dock (Rum~x crispus). Ample seeds are planted to give about 20 to 50 seedlings per row after emergence depènding 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 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 0% representing no injury and 100% representing complete kill.
B. Postemergence Herbicide Screening Test; Seeds of six plant species, including hairy crabgrass, watergrass, red oat, mustard, curly dock and Pinto beans (Phaseolus vulgaris) are * - Trademark -- 11 -- .
planted in the Styrofoam* flats as described above for preemergence screening. The flats are placed in the greenhouse at 70 to 85F
and watered daily with a sprinkler. ~bout 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 weigh-ing out 20 mg of the test compound, dissolving it in 5 ml of ace-tone containing 1% Tween 20 ~ and then adding 5 ml of water. The solution is sprayed on the foliage using a No. 152 DeVilbiss*
atomizer at an air pressure of 5 lb/sq. in. The spray concentra-tion is 0.2% and the rate is 8 lb/acre. The spray volume is 476 gal/acre.
The results of these tests are shown in Table II.
_ABLE II
~15 HERBICIDIAL ACTIVITY - SCREENING RESULTS
Percent Control * at 8 lb/A
Compound Number ~ Postemergence 99.9 77 7 99.7 74 9 99.7 83 12 99.7 79 * - Trademark ~ - 12 -~1~5126 , TABLE II...Continued Compound Percent Çontrol * at 8 lb/A
Number Preemer~ence Postemergence 22 30 o * ~verage for seven plant species in the preemergence test and for six plant species in the postemergence test.
Compound Percent Control * at Number 20 lb/A Preemer~ence * Average for seven species.
~CH2 C~
S i C3H7 \ ~CH2 . /CH2 C~
6 i-C3H7 \ /CH2 2 ~CH2-CH
7 C3H6 Cl \ ~CH2 115~
TABLE I . . . Con t inued Compound Number R Rl and R2 n CH" -CH
8 C3H6 ClCIH--CH2 2 2 9 n-C4H9 2--CH---CH-- 2 '--CH2 -C~ H2 CH -CH -CH
-i-C H~ 2 2 1 2 3 7~ CH2 -CH2 -CH2 12 -n-C H 2 CH
3 7~ CH--CH2-- 2 13 -n-C3H7CH2-CH2-JCH2 14 -n-C4HgCH2-CH2-CIH2 ~i~C4HgCH2-CH2-fH2 lSS5~Z6 TABLE I...Continued Compound N~nnber R R and R n Cl 2H5 16 n C3H6 Cl --CH--CF~CH2 CH2-CH ~' 17 -C2H5 =C~CH~ H2 ,,b2H5 Cl 2H5 18 -CH3~CI H--CH2 2 Cl 2H5 ~CH,~ ~CH
19 -C2H5~ ICH--CH2 2 .CH2-CH
-n-C3H7--CH--CH2 2 ~H3 C~ 2H5 21 -n-C4H9 ~ CH--CH-- H2 TABLE I...Continued Compound Number R Rand R n ~2H5 22 -i-C4Hg CH2-CH
23 -sec-c4H9 - CH- CH - H2 Herbicidal Screenin~ Tests As previously mentioned, the novel compounds herein described are phytotoxic compounds which are useful and valuable in controlling various plants species. Compounds of this inven-tion are tested as herbicides in the following manner.
A. Preemer~ence Herbicide Screenin~ Test: Using an analyti-cal balance, 20 mg of the compound to be tested i8 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 con-taining l~/o Tween 20 ~ is added to dissolve the compound. If the material is not soluble in acetone, another solvent such as water, alcohol or dimethylformamide (DMF) is used instead. When DMF is used, only 0.5 ml or less is uæed to dissolve the compound and llSS~Z6 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 ~t a pressure of 5 lb/sq.in. The rate of application is 8 lb/acre and the spray volume is 143 gal/acre.
On the day preceding treatment, the Styrofoam 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. The seeds used are hairy crabgrass (Di~itaria sanguinalis), yellow foxtail (Setaria ~lauca), watergrass ( chinochl-oa crusgalli), red oat (Avena sativa), redroot pigweed (Amaranthus retroflexus), Indian mustard (Brassica ~uncea) and curly dock (Rum~x crispus). Ample seeds are planted to give about 20 to 50 seedlings per row after emergence depènding 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 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 0% representing no injury and 100% representing complete kill.
B. Postemergence Herbicide Screening Test; Seeds of six plant species, including hairy crabgrass, watergrass, red oat, mustard, curly dock and Pinto beans (Phaseolus vulgaris) are * - Trademark -- 11 -- .
planted in the Styrofoam* flats as described above for preemergence screening. The flats are placed in the greenhouse at 70 to 85F
and watered daily with a sprinkler. ~bout 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 weigh-ing out 20 mg of the test compound, dissolving it in 5 ml of ace-tone containing 1% Tween 20 ~ and then adding 5 ml of water. The solution is sprayed on the foliage using a No. 152 DeVilbiss*
atomizer at an air pressure of 5 lb/sq. in. The spray concentra-tion is 0.2% and the rate is 8 lb/acre. The spray volume is 476 gal/acre.
The results of these tests are shown in Table II.
_ABLE II
~15 HERBICIDIAL ACTIVITY - SCREENING RESULTS
Percent Control * at 8 lb/A
Compound Number ~ Postemergence 99.9 77 7 99.7 74 9 99.7 83 12 99.7 79 * - Trademark ~ - 12 -~1~5126 , TABLE II...Continued Compound Percent Çontrol * at 8 lb/A
Number Preemer~ence Postemergence 22 30 o * ~verage for seven plant species in the preemergence test and for six plant species in the postemergence test.
Compound Percent Control * at Number 20 lb/A Preemer~ence * Average for seven species.
Claims (54)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A compound represented by the following generic formula:
wherein n is 1 or 2; R is selected from the group consisting of lower alkyl and halo-lower alkyl; R1 and R2 taken together can form an alkylene group having 5 or 6 carbon atoms, alkyl having 1 to 4 carbon atoms substituted alkylene group having 5 or 6 carbon atoms or .
wherein n is 1 or 2; R is selected from the group consisting of lower alkyl and halo-lower alkyl; R1 and R2 taken together can form an alkylene group having 5 or 6 carbon atoms, alkyl having 1 to 4 carbon atoms substituted alkylene group having 5 or 6 carbon atoms or .
2. The compound as set forth in Claim 1 wherein R
is -C2H5 , R1 and R2 are and n is 1.
is -C2H5 , R1 and R2 are and n is 1.
3. The compound as set forth in Claim 1 wherein R
is -C2H5 , R1 and R2 are and n is 2.
is -C2H5 , R1 and R2 are and n is 2.
4. The compound as set forth in Claim 1 wherein R
is n-C3H7 , R1 and R2 are and n is 1.
is n-C3H7 , R1 and R2 are and n is 1.
5. The compound as set forth in Claim 1 wherein R
is n-C3H7 , R1 and R2 are and n is 2.
is n-C3H7 , R1 and R2 are and n is 2.
6. The compound as set forth in Claim 1 wherein R
is i-C3H7, R1 and R2 are and n is 1.
is i-C3H7, R1 and R2 are and n is 1.
7. The compound as set forth in Claim 1 wherein R
is i-C3H7, R1 and R2 are and n is 2.
is i-C3H7, R1 and R2 are and n is 2.
8. The compound as set forth in Claim 1 wherein R
is -C3H6-Cl , R1 and R2 are and n is 1.
is -C3H6-Cl , R1 and R2 are and n is 1.
9. The compound as set forth in Claim 1 wherein R
is -C3H6-Cl , R1 and R2 a and n is 2.
is -C3H6-Cl , R1 and R2 a and n is 2.
10. The compound as set forth in Claim 1 wherein R
is n-C4H9 , R1 and R2 are and n is 1.
is n-C4H9 , R1 and R2 are and n is 1.
11. The compound as set forth in Claim 1 wherein R
is -i-C3H7, R1 and R2 are and n is 1.
is -i-C3H7, R1 and R2 are and n is 1.
12. The compound as set forth in Claim 1 wherein R
is -C2H5, R1 and R2 are and n is 1.
is -C2H5, R1 and R2 are and n is 1.
13. The compound as set forth in Claim 1 wherein R
is -n-C3H7, R1 and R2 are and n is 1.
is -n-C3H7, R1 and R2 are and n is 1.
14. The compound as set forth in Claim 1 wherein R
is -n-C3H7, R1 and R2 are and n is 1.
is -n-C3H7, R1 and R2 are and n is 1.
15. The compound as set forth in Claim 1 wherein R
is -n-C4H9, R1 and R2 are and n is 1.
is -n-C4H9, R1 and R2 are and n is 1.
16. The compound as set forth in Claim 1 wherein R is -i-C4H9, R1 and R2 are and n is 1.
17. The compound as set forth in Claim 1 wherein R is -n-C3H6-Cl, R1 and R2 are and n is 1.
18. The compound as set forth in Claim 1 wherein R is -C2H5, R1 and R2 are and n is 1.
19. The compound as set forth in Claim 1 wherein R is -CH3, R1 and R2 are and n is 1.
20. The compound as set forth in Claim 1 wherein R is -C2H5, R1 and R2 are and n is 1.
21. The compound as set forth in Claim 1 wherein R is -n-C3H7, R1 and R2 are and n is 1.
22. The compound as set forth in Claim 1 wherein R is -n-C4H9, R1 and R2 are and n is 1.
23. The compound as set forth in Claim 1 wherein R is -i-C4H9, R1 and R2 are and n is 1.
24. The compound as set forth in Claim 1 wherein R is -sec-C4H9, R1 and R2 are and n is 1.
25. A method of controlling undesirable vegetation com-prising applying to the locus where control is desired an herbi-cidally effective amount of a compound represented by the follow-ing formula:
wherein n is 1 or 2; R is selected from the group consisting of lower alkyl and halo-lower alkyl; R1 and R2 taken together can form an alkylene group having 5 or 6 carbon atoms, alkyl having 1 to 4 carbon atoms substituted alkylene group having 5 or 6 carbon atoms, or
wherein n is 1 or 2; R is selected from the group consisting of lower alkyl and halo-lower alkyl; R1 and R2 taken together can form an alkylene group having 5 or 6 carbon atoms, alkyl having 1 to 4 carbon atoms substituted alkylene group having 5 or 6 carbon atoms, or
26. The method as set forth in Claim 25 wherein R is -C2H5, R1 and R2 are and n is 1.
27. The method as set forth in Claim 25 wherein R is -C2H5, R1 and R2 are and n is 2.
28. The method as set forth in Claim 25 wherein R is n-C3H7, R1 and R2 are and n is 1.
29. The method as set forth in Claim 25 wherein R is n-C3H7, R1 and R2 are and n is 2.
30 . The method as set forth in Claim 25 wherein R is i-C3H7, R1 and R2 are and n is 1.
31. The method as set forth in Claim 25 wherein R is i-C3H7, R1 and R2 are and n is 2.
32. The method as set forth in Claim 25 wherein R is -C3H6-Cl, R1 and R2 are and n is 1.
33. The method as set forth in Claim 25 wherein R is -C3H6-C1, R1 and R2 are and n is 2.
34. The method as set forth in Claim 25 wherein R is n-C4H9, R1 and R2 are and n is 1.
35 . The method as set forth in Claim 25 wherein R is -i-C3H7, R1 and R2 are and n is 1.
36. The method as set forth in Claim 25 wherein R is -C2H5, R1 and R2 are and n is 1.
37. The method as set forth in Claim 25 wherein R is -n-C3H7, R1 and R2 are and n is 1.
38. The method as set forth in Claim 25 wherein R is -n-C3H7, R1 and R2 are and n is 1.
39. The method as set forth in Claim 25 wherein R is -i-C4H9, R1 and R2 are and n is 1.
40. The method as set forth in Claim 25 wherein R is -i-C4H9, R1 and R2 are and n is 1.
41. The method as set forth in Claim 25 wherein R is -n-C3H6-C1, R1 and R2 are and n is 1.
42. The method as set forth in Claim 25 wherein R is -C2H5, R1 and R2 are and n is 1.
43. The method as set forth in Claim 25 wherein R is -CH3, R1 and R2 are and n is 1.
44. The method as set forth in Claim 25 wherein R is -C2H5, R1 and R2 are and n is 1.
45. The method as set forth in Claim 25 wherein R is -n-C3H7, R1 and R2 are and n is 1
46. The method as set forth in Claim 25 wherein R is -n-C4H9, R1 and R2 are and n is 1.
47. The method as set forth in Claim 25 wherein R is -i-C4H9, R1 and R2 are and n is 1.
48. The method as set forth in Claim 25 wherein R is -sec-C4H9, R1 and R2 are and n is 1.
49. A process for manufacturing pesticidal active com-pounds corresponding to the following formula:
wherein n is 1 or 2; R is selected from the group consisting of lower alkyl and halo-lower alkyl; R1 and R2 taken together form an alkylene group having 5 or 6 carbon atoms, alkyl having 1 to 4 carbon atoms substituted alkylene group having 5 or 6 carbon atoms or comprising the steps of:
a. combining an oxidizing agent selected from the group consisting of peracetic acid and m-chloro-peroxybenzoic acid and a thiocarbamate compound in a solvent system; said thiocarbamate having the following formula:
wherein R, R1 and R2 have been defined above;
b. maintaining the temperature between -25°C. and 60°C.;
c. said oxidizing agent being present in an amount of at least one stoichiometric equiva-lent and not more than two stoichiometric equiva-lents.
wherein n is 1 or 2; R is selected from the group consisting of lower alkyl and halo-lower alkyl; R1 and R2 taken together form an alkylene group having 5 or 6 carbon atoms, alkyl having 1 to 4 carbon atoms substituted alkylene group having 5 or 6 carbon atoms or comprising the steps of:
a. combining an oxidizing agent selected from the group consisting of peracetic acid and m-chloro-peroxybenzoic acid and a thiocarbamate compound in a solvent system; said thiocarbamate having the following formula:
wherein R, R1 and R2 have been defined above;
b. maintaining the temperature between -25°C. and 60°C.;
c. said oxidizing agent being present in an amount of at least one stoichiometric equiva-lent and not more than two stoichiometric equiva-lents.
50. The process as set forth in Claim 49 wherein said oxidizing agent is m-chloroperoxybenzoic acid.
51 Compounds of the class of carbamoyl sulphoxides having the general formula:
wherein R represents alkyl containing 1 to 4 carbon atoms and which may be substituted with halogen, and wherein R1 and R2 taken together represent alkylene having 5 to 6 carbon atoms.
wherein R represents alkyl containing 1 to 4 carbon atoms and which may be substituted with halogen, and wherein R1 and R2 taken together represent alkylene having 5 to 6 carbon atoms.
52 The compound having the formula:
.
.
53 A process for manufacturing a compound having the general formula:
wherein R represents alkyl containing 1 to 4 carbon atoms and which may be substituted with halogen, and wherein R1 and R2 taken together represent alkylene having 5 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 thio-carbamate, said thiocarbamate having the general formula:
wherein R, 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.
wherein R represents alkyl containing 1 to 4 carbon atoms and which may be substituted with halogen, and wherein R1 and R2 taken together represent alkylene having 5 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 thio-carbamate, said thiocarbamate having the general formula:
wherein R, 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.
54 A method of controlling undesirable vegetation comp-rising applying to the locus where control is desired an effective amount of a compound represented by the general formula:
wherein R represents alkyl containing 1 to 4 carbon atoms and which may be substituted with halogen, and wherein R1 and R2 taken together represent alkylene having 5 to 6 carbon atoms.
The method as set forth in claim C30 wherein R is -C2H5 and R1 together with R2 are .
wherein R represents alkyl containing 1 to 4 carbon atoms and which may be substituted with halogen, and wherein R1 and R2 taken together represent alkylene having 5 to 6 carbon atoms.
The method as set forth in claim C30 wherein R is -C2H5 and R1 together with R2 are .
Applications Claiming Priority (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28038572A | 1972-08-14 | 1972-08-14 | |
| US28038772A | 1972-08-14 | 1972-08-14 | |
| US28038872A | 1972-08-14 | 1972-08-14 | |
| US280,387 | 1972-08-14 | ||
| US280,385 | 1972-08-14 | ||
| US280,388 | 1972-08-14 | ||
| US37132573A | 1973-06-18 | 1973-06-18 | |
| US37109473A | 1973-06-18 | 1973-06-18 | |
| US37099273A | 1973-06-18 | 1973-06-18 | |
| US370,992 | 1973-06-18 | ||
| US371,094 | 1973-06-18 | ||
| US371,325 | 1973-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1155126A true CA1155126A (en) | 1983-10-11 |
Family
ID=27559549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000178802A Expired CA1155126A (en) | 1972-08-14 | 1973-08-14 | Herbicide compositions |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5612605B2 (en) |
| AU (1) | AU476894B2 (en) |
| CA (1) | CA1155126A (en) |
| FR (1) | FR2196121B1 (en) |
| GB (1) | GB1382967A (en) |
-
1973
- 1973-08-14 FR FR7329772A patent/FR2196121B1/fr not_active Expired
- 1973-08-14 GB GB3843673A patent/GB1382967A/en not_active Expired
- 1973-08-14 AU AU59234/73A patent/AU476894B2/en not_active Expired
- 1973-08-14 JP JP9125073A patent/JPS5612605B2/ja not_active Expired
- 1973-08-14 CA CA000178802A patent/CA1155126A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU476894B2 (en) | 1976-10-07 |
| FR2196121B1 (en) | 1977-08-12 |
| JPS4962639A (en) | 1974-06-18 |
| AU5923473A (en) | 1975-02-20 |
| FR2196121A1 (en) | 1974-03-15 |
| JPS5612605B2 (en) | 1981-03-23 |
| GB1382967A (en) | 1975-02-05 |
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