US2913327A - Certain thiolcarbamates and use as herbicides - Google Patents

Certain thiolcarbamates and use as herbicides Download PDF

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Publication number
US2913327A
US2913327A US559541A US55954156A US2913327A US 2913327 A US2913327 A US 2913327A US 559541 A US559541 A US 559541A US 55954156 A US55954156 A US 55954156A US 2913327 A US2913327 A US 2913327A
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US
United States
Prior art keywords
parts
mole
sodium
added
chloride
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 - Lifetime
Application number
US559541A
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English (en)
Inventor
Tilles Harry
Antognini Joe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Stauffer Chemical Co
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Stauffer Chemical Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to NL213753D priority Critical patent/NL213753A/xx
Priority to BE559977D priority patent/BE559977A/xx
Priority to BE571955D priority patent/BE571955A/xx
Priority to BE554214D priority patent/BE554214A/xx
Priority to NL108235D priority patent/NL108235C/xx
Priority to BE582794D priority patent/BE582794A/xx
Priority to NL232065D priority patent/NL232065A/xx
Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co
Priority to US559541A priority patent/US2913327A/en
Priority to FR1171404D priority patent/FR1171404A/fr
Priority to DEST1239A priority patent/DE1031571B/de
Priority to GB1845/57A priority patent/GB808753A/en
Priority to GB23841/57A priority patent/GB862548A/en
Priority to CH357238D priority patent/CH357238A/de
Priority to DEST12853A priority patent/DE1081715B/de
Priority to FR72159D priority patent/FR72159E/fr
Priority to GB31728/58A priority patent/GB868111A/en
Priority to DEST14328A priority patent/DE1082452B/de
Priority to FR777391A priority patent/FR74319E/fr
Priority to CH6652558A priority patent/CH371921A/de
Priority to GB30509/59A priority patent/GB862250A/en
Priority to FR806064A priority patent/FR77056E/fr
Priority to CH8043159A priority patent/CH368015A/de
Application granted granted Critical
Publication of US2913327A publication Critical patent/US2913327A/en
Priority to MY19622A priority patent/MY6200002A/xx
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01Q—ANTENNAS, i.e. RADIO AERIALS
    • H01Q1/00—Details of, or arrangements associated with, antennas
    • H01Q1/12—Supports; Mounting means
    • H01Q1/1235—Collapsible supports; Means for erecting a rigid antenna
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Definitions

  • Ethyl N N-di-n-propylthiolcarbamate Methyl ,N-di-n-propylthiolcarbamate. n-Propyl ,N-di-n-propylthiolcarbamate. Ethyl N,N-pentamethylenethiolcarbamate. n-Propyl N,N-pentamethylenethiolcarbamate. Isobutyl N.N-di-n-propylthiolcarbamate. n-Butyl N,N-di-n-propylthiolcarbamate.
  • N,N-di-n-butylthiolcarbamate Ethyl N,N-di-n-butylthiolcarbamate. sec-Butyl N,N-di-n-propylthiolcarbamate. n-Amyl N, -di-n-propylthiolcarbamate. n-Propyl N ,N-di-isopropylthiolcarbamate.
  • Example II (R-1607).
  • 38 parts (0.50 mole) of l-propanethiol, sodium dispersion equivalent to 9.2 parts (.40 mole) of sodium, and 65.5 parts (0.40 mole) of di-n-propylcarbamyl chloride are employed, there is obtained 70.3 parts (86.5% yield) of n-propyl N,N-din- Example Ill (R1880).
  • 9.12 parts (0.12 mole) of l-p-ropanethiol, sodium dispersion equivalent to 2.3 parts (0.10 mole) of sodium, and 19.2 parts (0.10 mole) of di-n-butylcarbamyl chloride are employed, there is obtained 20.4 parts (88.3% yield) of n-propyl N,
  • Example IV (R-1854).-When the general procedure of Example I is repeated except that 16.9 parts (0.188 mole) of Z-methyl-l-propanethiol, sodium dispersion equivalent to 3.45 parts (0.15 mole) of sodium and 24.5 parts (0.15 mole) of di-n-propylcarbamyl chloride are employed, there is obtained 25.2 parts (77.3% yield) of isobutyl N,N-di-n-propylthiolcarbamate (B.P. (18 mm.) 143145 0, n 1.4744).
  • Example V (RJ857).When the general procedure of Example I is repeated except that 16.9 parts (0.188 mole) of l-butanethiol, sodium dispersion equivalent to 3.45 parts (0.15 mole) sodium and 24.5 parts (0.15 mole) of di-n-propylcarbamyl chloride are employed, there is obtained 24.8 parts (76% yield) of n-butyl N,N-di-n-propyl- 3 thiolcarbamate (B.P. (19 mm.) l51.0-151.5' C., 11 1.4766).
  • Example VI (R-I866). The general procedure of Example I was followed except that 25 parts (0.52 mole) of methanethiol is added in small portions at 50-60 C. to the sodium dispersion equivalent to 2.3 parts (0.10 mole) of sodium. It is necessary to make sure that unreacted mercaptan does not build up in the reaction mixture since a violent reaction may take place if too much unreacted mercaptan is present with unreacted dispersion. After all of the sodium dispersion has reacted which is evidenced by the reaction mixture changing from a purplish hue to a white color, it is heated to reflux and 19.2 parts (0.10 mole) of di-n-butylcarbamyl chloride is added. After working up in the usual manner, there is obtained 13.9 parts (68.5% yield) of methyl N,N,-din-butylthiolcarbamate (B.P. (20 mm.) 144-146 C., n 1.4760).
  • Example X (R-1905).
  • Example VIII When the general procedure of Example VIII is repeated except that 13.0 parts (0.125 mole) of l-pentanethiol, 2.3 parts (0.10 mole) of sodium and 16.4 parts of di-isopropylcarbamyl chloride are employed, there is obtained 15.8 parts (68.3%) of n-amyl N,N,-di-isopropylthiolcarbamate (B.P. (22 mm.) 145- 149 C., a 1.4721).
  • Example XI (R-1824).Wl1en the general procedure of Example VIII is repeated except that 14.3 parts (0.188 mole) of 2-propanethiol, 3.45 parts (0.15 mole) of sodium and 22.1 parts (0.15 mole) of N,N-pentarnethyl-
  • Pre-emergence herbicides are ordinarily used by placing a narrow band of the herbicide over the center of a seeded crop row at time of planting or before crop emerges. If the herbicide is harmless to the desired crop, seeds or seedlings, but phytotoxic to the weed seeds or seedlings most frequently encountered, the crop grows in an almost weedfree environment.
  • the pre-emergence herbicide may be used over the entire field, but it is normally used in a narrow band which straddles the crop row and the balance of the weeds are controlled by various cultivation methods.
  • the herbicides of the present invention are selective toward small seeded annual grasses and broad-leafed plants, and so are efiective against the most common weeds but have little effect on such valuable row crops as corn and beans.
  • the phytocidal composition may be applied to the soil in any convenient form.
  • the method-of combatting weeds comprising ap- 2562911 fP July 1951 plying to the soil a phytotoxic amount of n-propyl N,N- 2642451 welllard et a1 June 1953 di n propylthiolcarbamate Kosmin g' 24! 12.
  • the method of combatting weeds comprising applying to the soil a phytotoxic amount of n-propy1'N,N- 10 OTHER REFERENCES di-n-butylthiolcarbamate.
  • the method of combatting weeds comprising ap- (1953).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US559541A 1956-01-17 1956-01-17 Certain thiolcarbamates and use as herbicides Expired - Lifetime US2913327A (en)

Priority Applications (23)

Application Number Priority Date Filing Date Title
BE559977D BE559977A (es) 1956-01-17
BE571955D BE571955A (es) 1956-01-17
BE554214D BE554214A (es) 1956-01-17
NL108235D NL108235C (es) 1956-01-17
NL213753D NL213753A (es) 1956-01-17
BE582794D BE582794A (es) 1956-01-17
NL232065D NL232065A (es) 1956-01-17
US559541A US2913327A (en) 1956-01-17 1956-01-17 Certain thiolcarbamates and use as herbicides
FR1171404D FR1171404A (fr) 1956-01-17 1957-01-15 Perfectionnements apportés aux herbicides et à leurs procédés de fabrication
DEST1239A DE1031571B (de) 1956-01-17 1957-01-17 Pflanzenvertilgungsmittel
GB1845/57A GB808753A (en) 1956-01-17 1957-01-17 Improvements in or relating to thiolcarbamates
GB23841/57A GB862548A (en) 1956-01-17 1957-07-26 Improvements in or relating to phytocidal compositions of matter
CH357238D CH357238A (de) 1956-01-17 1957-07-31 Unkrautvertilgungsmittel
DEST12853A DE1081715B (de) 1956-01-17 1957-08-06 Pflanzenvertilgungsmittel
FR72159D FR72159E (fr) 1956-01-17 1957-08-07 Perfectionnements apportés aux herbicides et à leurs procédé de fabrication
GB31728/58A GB868111A (en) 1956-01-17 1958-10-03 Improvements in or relating to thiolcarbamates
DEST14328A DE1082452B (de) 1956-01-17 1958-10-10 Pflanzenvertilgungsmittel
FR777391A FR74319E (fr) 1956-01-17 1958-10-23 Perfectionnements apportés aux herbicides et à leurs procédés de fabrication
CH6652558A CH371921A (de) 1956-01-17 1958-11-24 Unkrautvertilgungsmittel
GB30509/59A GB862250A (en) 1956-01-17 1959-09-07 Improvements in or relating to thiolcarbamates
FR806064A FR77056E (fr) 1956-01-17 1959-09-25 Perfectionnements apportés aux herbicides et à leurs procédés de fabrication
CH8043159A CH368015A (de) 1956-01-17 1959-11-10 Unkrautvertilgungsmittel
MY19622A MY6200002A (en) 1956-01-17 1962-12-31 Improvements in or relating to thiolcarbamates

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US559541A US2913327A (en) 1956-01-17 1956-01-17 Certain thiolcarbamates and use as herbicides

Publications (1)

Publication Number Publication Date
US2913327A true US2913327A (en) 1959-11-17

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Family Applications (1)

Application Number Title Priority Date Filing Date
US559541A Expired - Lifetime US2913327A (en) 1956-01-17 1956-01-17 Certain thiolcarbamates and use as herbicides

Country Status (8)

Country Link
US (1) US2913327A (es)
BE (4) BE559977A (es)
CH (3) CH357238A (es)
DE (3) DE1031571B (es)
FR (4) FR1171404A (es)
GB (4) GB808753A (es)
MY (1) MY6200002A (es)
NL (3) NL213753A (es)

Cited By (73)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3037853A (en) * 1958-04-04 1962-06-05 Du Pont Herbicidal composition and method employing a mixture of ethyl n, n-dipropylthiolcarbamate and a herbicidal s-triazine
US3046189A (en) * 1957-05-18 1962-07-24 Merck Ag E Nematocidal agents
US3095299A (en) * 1960-05-11 1963-06-25 Du Pont Herbicidal composition and method
US3101263A (en) * 1959-04-20 1963-08-20 Stauffer Chemical Co Herbicidal method
US3154402A (en) * 1962-03-12 1964-10-27 Exxon Research Engineering Co Wax formulations of thiolcarbamate herbicides
US3175897A (en) * 1962-08-21 1965-03-30 Stauffer Chemical Co Asymmetric thiolcarbamates as herbicides
US3185720A (en) * 1962-08-21 1965-05-25 Stauffer Chemical Co Asymmetric thiolcarbamates
US3198786A (en) * 1961-05-01 1965-08-03 Stauffer Chemical Co Alkyl hexamethylene-thiolcarbamates
US3298817A (en) * 1959-04-16 1967-01-17 Tilles Harry Method of combating weeds
US3305576A (en) * 1959-07-10 1967-02-21 Monsanto Co 3-chloropropyl diisopropylthiolcarbamate
US3893838A (en) * 1972-11-16 1975-07-08 Stauffer Chemical Co Halogenated esters as herbicide antidotes
US3923494A (en) * 1973-05-24 1975-12-02 Stauffer Chemical Co Gem-bis amide herbicide antidote compositions and methods of use
US3976469A (en) * 1972-11-16 1976-08-24 Stauffer Chemical Company Halogenated ketones as herbicide antidotes
US4021224A (en) * 1971-12-09 1977-05-03 Stauffer Chemical Company Herbicide compositions
US4036628A (en) * 1972-11-13 1977-07-19 Stauffer Chemical Company Phosphorus containing herbicide antidotes
US4098599A (en) * 1975-09-12 1978-07-04 Stauffer Chemical Company Antidote compositions and method of use with herbicides
US4137070A (en) * 1971-04-16 1979-01-30 Stauffer Chemical Company Herbicide compositions
US4208203A (en) * 1971-09-17 1980-06-17 Gulf Research & Development Co. Method of protecting corn from herbicides
US4222938A (en) * 1978-09-29 1980-09-16 Monsanto Company Preparation of thiolcarbamates
US4268456A (en) * 1979-09-24 1981-05-19 Ppg Industries, Inc. Process for preparing chlorothiolformates
US4273725A (en) * 1979-07-25 1981-06-16 Ppg Industries, Inc. Process for preparing chlorothiolformates
US4276078A (en) * 1978-08-04 1981-06-30 Stauffer Chemical Company Herbicide compositions
US4279638A (en) * 1979-08-13 1981-07-21 Stauffer Chemical Company 3,5-Disubstituted 1,2,4-oxadiazole herbicidal antidotes
EP0038945A2 (en) * 1980-03-31 1981-11-04 Stauffer Chemical Company Herbicide compositions of extended soil life
US4320070A (en) * 1979-09-24 1982-03-16 Ppg Industries, Inc. Process for preparing chlorothiolformates
US4321083A (en) * 1980-04-21 1982-03-23 Stauffer Chemical Company N-Acyl-phenyl-thiourea herbicidal antidotes
US4321084A (en) * 1977-09-23 1982-03-23 Stauffer Chemical Company Certain halogenated phenols as antidotes for thiocarbamate herbicides
US4338120A (en) * 1980-04-21 1982-07-06 Stauffer Chemical Company Halo-substituted thionoacyl ketone herbicidal antidotes
FR2509136A1 (fr) * 1981-07-08 1983-01-14 Eszakmagyar Vegyimuevek Composition herbicide contenant un melange de deux esters d'acides thiocarbamiques
US4378239A (en) * 1981-04-27 1983-03-29 Stauffer Chemical Company N-Methylcarbamoyloxy benzaldehyde imine herbicide extenders
US4380467A (en) * 1981-03-12 1983-04-19 Stauffer Chemical Company Amine oxanilic acid salts as herbicide extenders
US4380468A (en) * 1980-10-14 1983-04-19 Stauffer Chemical Company Isonitriles as herbicide extenders
US4381195A (en) * 1981-04-20 1983-04-26 Stauffer Chemical Company N-Methylcarbamoyloxy anilides as herbicide extenders
US4381196A (en) * 1981-04-20 1983-04-26 Stauffer Chemical Company O-(Substituted phenyl) N-methylcarbamates as herbicide extenders
US4381936A (en) * 1980-03-31 1983-05-03 Stauffer Chemical Company Herbicide compositions of extended soil life
US4386955A (en) * 1981-04-20 1983-06-07 Stauffer Chemical Company O-(Substituted phenyl) N-methylcarbamates as herbicide extenders
US4396419A (en) * 1981-03-16 1983-08-02 Stauffer Chemical Company Chloroacetamido alkoxy ethane herbicide antidotes
US4400197A (en) * 1979-12-26 1983-08-23 Ppg Industries, Inc. N-(Optionally substituted 1,3-dioxolan- or dioxan-2-ylmethyl)-N-alkyl, alkenyl, or alkynyl-2,2-dichloroacetamides
US4420323A (en) * 1982-05-10 1983-12-13 Stauffer Chemical Company Thiophosphoryl carbamate herbicide antidotes
US4420322A (en) * 1979-04-02 1983-12-13 Stauffer Chemical Company Herbicidal antidotes
US4422869A (en) * 1981-04-20 1983-12-27 Stauffer Chemical Company Halogenated allylthioisopropyl N-methylcarbamates as herbicide extenders
US4432909A (en) * 1981-03-12 1984-02-21 Stauffer Chemical Company Amine oxanilic acid salts as herbicide extenders
US4433999A (en) 1981-07-20 1984-02-28 Stauffer Chemical Company Herbicide compositions containing soil life extenders and antidotes
US4441916A (en) * 1981-10-19 1984-04-10 Stauffer Chemical Company Haloalkyloxime herbicidal antidotes
US4478636A (en) * 1982-06-01 1984-10-23 Stauffer Chemical Company Herbicidal compositions of extended soil life
US4490166A (en) * 1982-06-01 1984-12-25 Stauffer Chemical Company Iminophenyl N-methylcarbamates as herbicide extenders
US4495365A (en) * 1980-11-21 1985-01-22 Stauffer Chemical Co. N-Acylsulfonamide herbicidal antidotes
US4517012A (en) * 1979-07-09 1985-05-14 Stauffer Chemical Company Herbicide compositions
US4540429A (en) * 1981-03-16 1985-09-10 Stauffer Chemical Company 4-Phenyl-1,2,3-thiadiazoles as herbicide extenders
US4546199A (en) * 1981-04-20 1985-10-08 Stauffer Chemical Company Halogenated allylthioisopropyl N-methyl carbamates as herbicide extenders
US4545805A (en) * 1982-03-24 1985-10-08 Stauffer Chemical Company Herbicide compositions of extended soil life
US4559082A (en) * 1983-08-12 1985-12-17 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4613358A (en) * 1983-05-20 1986-09-23 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4648894A (en) * 1983-05-20 1987-03-10 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4650516A (en) * 1979-03-23 1987-03-17 Stauffer Chemical Co. α-halo-Ω-haloalkylamides herbicidal antidotes
US4652300A (en) * 1983-05-16 1987-03-24 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4652298A (en) * 1983-05-16 1987-03-24 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4652296A (en) * 1983-05-16 1987-03-24 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4652302A (en) * 1983-05-20 1987-03-24 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4652301A (en) * 1983-05-16 1987-03-24 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4662930A (en) * 1983-05-20 1987-05-05 Stauffer Chemical Co. Herbicide compositions of extended soil life
WO1989009208A1 (en) * 1988-03-30 1989-10-05 Bio-Tox Diagnostics Kommanditbolag Carbamic acid ester and a preparation thereof for treatment of addiction to alcohol
US4915725A (en) * 1978-09-20 1990-04-10 Ici Americas, Inc. Herbicide compositions of extended soil life
US5011526A (en) * 1978-09-20 1991-04-30 Ici Americas Inc. Herbicide compositions of extended soil life
US5041599A (en) * 1990-07-30 1991-08-20 Phillips Petroleum Company Catalytic synthesis of thionocarbamates from xanthates and amines
US5171356A (en) * 1984-09-19 1992-12-15 Ici Americas Inc. Herbicide compositions of extended soil life
US5527762A (en) * 1990-12-12 1996-06-18 Zeneca Limited Antidoting herbicidal 3-isoxazolidinone compounds
EP2052606A1 (de) 2007-10-24 2009-04-29 Bayer CropScience AG Herbizid-Kombination
DE102008037620A1 (de) 2008-08-14 2010-02-18 Bayer Crop Science Ag Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden
WO2012049266A1 (en) 2010-10-15 2012-04-19 Bayer Cropscience Ag Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant beta vulgaris plants
WO2012150333A1 (en) 2011-05-04 2012-11-08 Bayer Intellectual Property Gmbh Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant brassica, such as b. napus, plants
WO2014090760A1 (en) 2012-12-13 2014-06-19 Bayer Cropscience Ag Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant beta vulgaris plants
WO2023062184A1 (en) 2021-10-15 2023-04-20 KWS SAAT SE & Co. KGaA Als inhibitor herbicide tolerant beta vulgaris mutants

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE571955A (es) * 1956-01-17
DE1142464B (de) * 1959-05-11 1963-01-17 Monsanto Chemicals Bekaempfung unerwuenschten Pflanzenwuchses, Unkrautvertilgung, Entblaetterung, Bodenentseuchung, Fungi- und Nematodenbekaempfung
US3318676A (en) * 1959-07-10 1967-05-09 Monsanto Co Controlling vegetation with haloalkyl thiolcarbamates
US3839010A (en) * 1970-05-19 1974-10-01 Exxon Research Engineering Co Thiocarbamic acid ester pesticides
DE2329043A1 (de) * 1973-06-07 1975-01-02 Basf Ag Carbothiolate
US4056549A (en) 1976-06-07 1977-11-01 Ppg Industries, Inc. S-3-Methoxyphenyl N-alkylthiolcarbamates and S-3-methylthiophenyl N-alkylthiolcarbamates
ES493517A0 (es) * 1979-07-25 1981-05-16 Hoechst Ag Procedimiento para la preparacion de anilidas de acido tio- glicolico, fungicidas
AU549319B2 (en) * 1980-10-21 1986-01-23 Hodogaya Chemical Co. Ltd. Nematocide

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2060733A (en) * 1934-09-04 1936-11-10 Du Pont Process of treating cellulose and derivatives thereof
US2160880A (en) * 1936-11-02 1939-06-06 Standard Oil Co Lubricant
US2562011A (en) * 1948-12-10 1951-07-24 Goodrich Co B F Herbicidal compositions and application thereof
US2642451A (en) * 1953-06-16 Thiolurethanes and processes for
US2687348A (en) * 1952-09-17 1954-08-24 Monsanto Chemicals Herbicidal compositions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE858352C (de) * 1948-10-02 1952-12-04 Schering Ag Verhinderung der Keimung bei Hackfruechten u. dgl.
BE571955A (es) * 1956-01-17

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2642451A (en) * 1953-06-16 Thiolurethanes and processes for
US2060733A (en) * 1934-09-04 1936-11-10 Du Pont Process of treating cellulose and derivatives thereof
US2160880A (en) * 1936-11-02 1939-06-06 Standard Oil Co Lubricant
US2562011A (en) * 1948-12-10 1951-07-24 Goodrich Co B F Herbicidal compositions and application thereof
US2687348A (en) * 1952-09-17 1954-08-24 Monsanto Chemicals Herbicidal compositions

Cited By (82)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3046189A (en) * 1957-05-18 1962-07-24 Merck Ag E Nematocidal agents
US3037853A (en) * 1958-04-04 1962-06-05 Du Pont Herbicidal composition and method employing a mixture of ethyl n, n-dipropylthiolcarbamate and a herbicidal s-triazine
US3298817A (en) * 1959-04-16 1967-01-17 Tilles Harry Method of combating weeds
US3101263A (en) * 1959-04-20 1963-08-20 Stauffer Chemical Co Herbicidal method
US3305576A (en) * 1959-07-10 1967-02-21 Monsanto Co 3-chloropropyl diisopropylthiolcarbamate
US3095299A (en) * 1960-05-11 1963-06-25 Du Pont Herbicidal composition and method
US3198786A (en) * 1961-05-01 1965-08-03 Stauffer Chemical Co Alkyl hexamethylene-thiolcarbamates
US3154402A (en) * 1962-03-12 1964-10-27 Exxon Research Engineering Co Wax formulations of thiolcarbamate herbicides
US3175897A (en) * 1962-08-21 1965-03-30 Stauffer Chemical Co Asymmetric thiolcarbamates as herbicides
US3185720A (en) * 1962-08-21 1965-05-25 Stauffer Chemical Co Asymmetric thiolcarbamates
US4137070A (en) * 1971-04-16 1979-01-30 Stauffer Chemical Company Herbicide compositions
US4208203A (en) * 1971-09-17 1980-06-17 Gulf Research & Development Co. Method of protecting corn from herbicides
US4021224A (en) * 1971-12-09 1977-05-03 Stauffer Chemical Company Herbicide compositions
US4036628A (en) * 1972-11-13 1977-07-19 Stauffer Chemical Company Phosphorus containing herbicide antidotes
US3893838A (en) * 1972-11-16 1975-07-08 Stauffer Chemical Co Halogenated esters as herbicide antidotes
US3976469A (en) * 1972-11-16 1976-08-24 Stauffer Chemical Company Halogenated ketones as herbicide antidotes
US3923494A (en) * 1973-05-24 1975-12-02 Stauffer Chemical Co Gem-bis amide herbicide antidote compositions and methods of use
US4098599A (en) * 1975-09-12 1978-07-04 Stauffer Chemical Company Antidote compositions and method of use with herbicides
US4321084A (en) * 1977-09-23 1982-03-23 Stauffer Chemical Company Certain halogenated phenols as antidotes for thiocarbamate herbicides
US4276078A (en) * 1978-08-04 1981-06-30 Stauffer Chemical Company Herbicide compositions
US5011526A (en) * 1978-09-20 1991-04-30 Ici Americas Inc. Herbicide compositions of extended soil life
US4915725A (en) * 1978-09-20 1990-04-10 Ici Americas, Inc. Herbicide compositions of extended soil life
US4222938A (en) * 1978-09-29 1980-09-16 Monsanto Company Preparation of thiolcarbamates
US4650516A (en) * 1979-03-23 1987-03-17 Stauffer Chemical Co. α-halo-Ω-haloalkylamides herbicidal antidotes
US4420322A (en) * 1979-04-02 1983-12-13 Stauffer Chemical Company Herbicidal antidotes
US4517012A (en) * 1979-07-09 1985-05-14 Stauffer Chemical Company Herbicide compositions
US4273725A (en) * 1979-07-25 1981-06-16 Ppg Industries, Inc. Process for preparing chlorothiolformates
US4279638A (en) * 1979-08-13 1981-07-21 Stauffer Chemical Company 3,5-Disubstituted 1,2,4-oxadiazole herbicidal antidotes
US4320070A (en) * 1979-09-24 1982-03-16 Ppg Industries, Inc. Process for preparing chlorothiolformates
US4268456A (en) * 1979-09-24 1981-05-19 Ppg Industries, Inc. Process for preparing chlorothiolformates
US4400197A (en) * 1979-12-26 1983-08-23 Ppg Industries, Inc. N-(Optionally substituted 1,3-dioxolan- or dioxan-2-ylmethyl)-N-alkyl, alkenyl, or alkynyl-2,2-dichloroacetamides
US4381936A (en) * 1980-03-31 1983-05-03 Stauffer Chemical Company Herbicide compositions of extended soil life
EP0038945A2 (en) * 1980-03-31 1981-11-04 Stauffer Chemical Company Herbicide compositions of extended soil life
US4299616A (en) * 1980-03-31 1981-11-10 Stauffer Chemical Company Herbicide compositions of extended soil life
EP0038945A3 (en) * 1980-03-31 1981-12-16 Stauffer Chemical Company Herbicide compositions of extended soil life
US4338120A (en) * 1980-04-21 1982-07-06 Stauffer Chemical Company Halo-substituted thionoacyl ketone herbicidal antidotes
US4321083A (en) * 1980-04-21 1982-03-23 Stauffer Chemical Company N-Acyl-phenyl-thiourea herbicidal antidotes
US4380468A (en) * 1980-10-14 1983-04-19 Stauffer Chemical Company Isonitriles as herbicide extenders
US4495365A (en) * 1980-11-21 1985-01-22 Stauffer Chemical Co. N-Acylsulfonamide herbicidal antidotes
US4432909A (en) * 1981-03-12 1984-02-21 Stauffer Chemical Company Amine oxanilic acid salts as herbicide extenders
US4380467A (en) * 1981-03-12 1983-04-19 Stauffer Chemical Company Amine oxanilic acid salts as herbicide extenders
US4540429A (en) * 1981-03-16 1985-09-10 Stauffer Chemical Company 4-Phenyl-1,2,3-thiadiazoles as herbicide extenders
US4396419A (en) * 1981-03-16 1983-08-02 Stauffer Chemical Company Chloroacetamido alkoxy ethane herbicide antidotes
US4422869A (en) * 1981-04-20 1983-12-27 Stauffer Chemical Company Halogenated allylthioisopropyl N-methylcarbamates as herbicide extenders
US4381196A (en) * 1981-04-20 1983-04-26 Stauffer Chemical Company O-(Substituted phenyl) N-methylcarbamates as herbicide extenders
US4546199A (en) * 1981-04-20 1985-10-08 Stauffer Chemical Company Halogenated allylthioisopropyl N-methyl carbamates as herbicide extenders
US4381195A (en) * 1981-04-20 1983-04-26 Stauffer Chemical Company N-Methylcarbamoyloxy anilides as herbicide extenders
US4386955A (en) * 1981-04-20 1983-06-07 Stauffer Chemical Company O-(Substituted phenyl) N-methylcarbamates as herbicide extenders
US4378239A (en) * 1981-04-27 1983-03-29 Stauffer Chemical Company N-Methylcarbamoyloxy benzaldehyde imine herbicide extenders
FR2509136A1 (fr) * 1981-07-08 1983-01-14 Eszakmagyar Vegyimuevek Composition herbicide contenant un melange de deux esters d'acides thiocarbamiques
US4433999A (en) 1981-07-20 1984-02-28 Stauffer Chemical Company Herbicide compositions containing soil life extenders and antidotes
US4441916A (en) * 1981-10-19 1984-04-10 Stauffer Chemical Company Haloalkyloxime herbicidal antidotes
US4545805A (en) * 1982-03-24 1985-10-08 Stauffer Chemical Company Herbicide compositions of extended soil life
US4420323A (en) * 1982-05-10 1983-12-13 Stauffer Chemical Company Thiophosphoryl carbamate herbicide antidotes
US4490166A (en) * 1982-06-01 1984-12-25 Stauffer Chemical Company Iminophenyl N-methylcarbamates as herbicide extenders
US4478636A (en) * 1982-06-01 1984-10-23 Stauffer Chemical Company Herbicidal compositions of extended soil life
US4652301A (en) * 1983-05-16 1987-03-24 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4652300A (en) * 1983-05-16 1987-03-24 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4652298A (en) * 1983-05-16 1987-03-24 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4652296A (en) * 1983-05-16 1987-03-24 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4613358A (en) * 1983-05-20 1986-09-23 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4652302A (en) * 1983-05-20 1987-03-24 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4662930A (en) * 1983-05-20 1987-05-05 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4648894A (en) * 1983-05-20 1987-03-10 Stauffer Chemical Co. Herbicide compositions of extended soil life
US4559082A (en) * 1983-08-12 1985-12-17 Stauffer Chemical Co. Herbicide compositions of extended soil life
US5171356A (en) * 1984-09-19 1992-12-15 Ici Americas Inc. Herbicide compositions of extended soil life
WO1989009208A1 (en) * 1988-03-30 1989-10-05 Bio-Tox Diagnostics Kommanditbolag Carbamic acid ester and a preparation thereof for treatment of addiction to alcohol
US5100916A (en) * 1988-03-30 1992-03-31 Bio-Tox Diagnostics Kommanditbolag Carbamic acid ester for treatment of addiction to alcohol
US5041599A (en) * 1990-07-30 1991-08-20 Phillips Petroleum Company Catalytic synthesis of thionocarbamates from xanthates and amines
US5527762A (en) * 1990-12-12 1996-06-18 Zeneca Limited Antidoting herbicidal 3-isoxazolidinone compounds
US5527761A (en) * 1990-12-12 1996-06-18 Zeneca Limited Antidoting herbicidal 3-isoxazolidinone compounds
EP2052606A1 (de) 2007-10-24 2009-04-29 Bayer CropScience AG Herbizid-Kombination
DE102008037620A1 (de) 2008-08-14 2010-02-18 Bayer Crop Science Ag Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden
US20100099564A1 (en) * 2008-08-14 2010-04-22 Bayer Cropscience Ag Herbicide combination comprising dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
WO2012049266A1 (en) 2010-10-15 2012-04-19 Bayer Cropscience Ag Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant beta vulgaris plants
EP3284346A1 (en) 2010-10-15 2018-02-21 Bayer Intellectual Property GmbH Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant beta vulgaris plants
US10544426B2 (en) 2010-10-15 2020-01-28 Bayer Intellectual Property Gmbh Methods of using ALS inhibitor herbicides for control of unwanted vegetation in ALS inhibitor herbicide tolerant beta vulgaris plants
US11371057B2 (en) 2010-10-15 2022-06-28 Bayer Intellectual Property Gmbh Methods of using ALS inhibitor herbicides for control of unwanted vegetation in ALS inhibitor herbicide tolerant beta vulgaris plants
WO2012150333A1 (en) 2011-05-04 2012-11-08 Bayer Intellectual Property Gmbh Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant brassica, such as b. napus, plants
US9370183B2 (en) 2011-05-04 2016-06-21 Bayer Intellectual Property Gmbh Use of ALS inhibitor herbicides for control of unwanted vegetation in ALS inhibitor herbicide tolerant Brassica, such as B. napus, plants
WO2014090760A1 (en) 2012-12-13 2014-06-19 Bayer Cropscience Ag Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant beta vulgaris plants
WO2023062184A1 (en) 2021-10-15 2023-04-20 KWS SAAT SE & Co. KGaA Als inhibitor herbicide tolerant beta vulgaris mutants

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GB808753A (en) 1959-02-11
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FR77056E (fr) 1962-01-12
BE582794A (es)
BE554214A (es)
MY6200002A (en) 1962-12-31
FR1171404A (fr) 1959-01-26
NL213753A (es)
CH371921A (de) 1963-09-15
BE559977A (es)
CH357238A (de) 1961-09-30
FR72159E (fr) 1960-03-30
NL232065A (es)
FR74319E (fr) 1960-11-07
GB862548A (en) 1961-03-15
DE1031571B (de) 1958-06-04
NL108235C (es)
DE1081715B (de) 1960-05-12
GB862250A (en) 1961-03-08

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