cas 28249-77-6, Thiobencarb | Articles data

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Solvent-assisted thiocarboxylation of amines and alcohols with carbon monoxide and sulfur under mild conditions
DMSO or DMF as a solvent strongly accelerated the thiocarboxylation of amines and alcohols with carbon monoxide and sulfur. Under mild conditions (1 atm, 20°C), this thiocarboxylation of amines assisted by DMSO with carbon monoxide and sulfur has been developed into a practical and convenient synthetic method for S-alkyl thiocarbamates in good to excellent yields, including EPTC, thiobencarb, orbencarb, and molinate (herbicides). DMF also showed the similar solvent effect. NMP slightly decreased the effect for the thiocarboxylation of amines, and the yield of S-alkyl thiocarbamate was lowered in DMAc. Surprisingly, no formation of S-alkyl thiocarbamate was observed at the use of the other solvents, such as THF, hexane, toluene, AcOEt, MeCN, MeOH, and H 2O. The present solvent-assisted thiocarboxylation with carbon monoxide and sulfur could be also applied to a new synthesis of S-alkyl O-alkyl carbonothioates from alcohols under mild conditions (1 atm, 20°C) in DMF using DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).
Mizuno, Takumi,Iwai, Toshiyuki,Ishino, Yoshio
p. 9157 - 9163
(2007/10/03)

Practical synthesis of S-alkyl thiocarbamate herbicides by carbonylation of amines with carbon monoxide and sulfur
An industrial and economic carbonylation of amines with carbon monoxide and sulfur has been developed for the synthesis of S-alkyl thiocarbamate herbicides. In the presence of potassium carbonate and solvent DMSO, S-alkyl thiocarbamates, such as thiobencarb and orbencarb (herbicides) are synthesized in excellent yields from amines, carbon monoxide, sulfur, and alkyl halides under mild conditions (1atm, 20°C).
Mizuno, Takumi,Iwai, Toshiyuki,Ito, Takatoshi
p. 2869 - 2873
(2007/10/03)

Facile one-pot synthesis of S-alkyl thiocarbamates
We report a novel one-pot two-step synthesis of a variety of S-alkyl thiocarbamates. This method offers a two-directional approach making use of trichloroacetyl chloride, requires no complex starting material, incorporates a variety of substituents, and proceeds in high yields.
Wynne, James H.,Jensen, Samuel D.,Snow, Arthur W.
p. 3733 - 3735
(2007/10/03)

Facile S-alkyl thiocarbamate synthesis by a novel DBU-assisted carbonylation of amines with carbon monoxide and sulfur
A novel DBU-assisted carbonylation of amines with carbon monoxide and sulfur has been developed for the synthesis of S-alkyl thiocarbamates. In the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), S-alkyl thiocarbamates are synthesized in excellent yields from amines, carbon monoxide, sulfur, and alkyl halides under mild conditions (1 atm, 20°C). In the absence of DBU, however, no formation of S-alkyl thiocarbamate is observed. The present DBU-assisted carbonylation can also be applied to new synthetic methods for benthiocarb and orthobencarb (herbicides) and carbamoyl chlorides.
Mizuno, Takumi,Takahashi, Junko,Ogawa, Akiya
p. 1327 - 1331
(2007/10/03)

Synergistic herbicidal mixtures
PCT No. PCT/EP96/04935 Sec. 371 Date May 1, 1998 Sec. 102(e) Date May 1, 1998 PCT Filed Nov. 12, 1996 PCT Pub. No. WO97/17852 PCT Pub. Date May 22, 1997A synergistically active herbicidal composition which comprises, as active components, a mixture of 1-(3-chloro-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile [Component (A)] and a herbicide selected from the group consisting of bentazone, molinate, daimuron, thiobencarb, butachlor, pretilachlor, dimepiperate, fenoxaprop-ethyl, clomeprop, cinmethylin, bromobutide, quinclorac, mefenacet, pyrazosulfuron-ethyl, esprocarb, cinosulfuron, thenylchlor, cumyluron, MK 243, naproanilide, anilofos, benfuresate, bifenox, CH-900, MCPA, nitrofen, oxadiazon, pendimethalin, simetryn, sulcotrione (ICIA0051), trifluralin, piperophos, pyributicarb, ethoxysulfuron, bensulfuronmethyl, pyrazolate, pyrazoxyfen, benzofenap, cyclosulfamuron, cyhalofop-butyl, NBA-061, azimsulfuron, propanil or imazosulfuron [Component (B)] and which are suitable for controlling undesirable plants in rice cultivation.
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(2008/06/13)

Herbicidal mixtures having a synergistic effect
PCT No. PCT/EP96/03996 Sec. 371 Date Feb. 17, 1998 Sec. 102(e) Date Feb. 17, 1998 PCT Filed Sep. 12, 1996 PCT Pub. No. WO97/10714 PCT Pub. Date Mar. 27, 1997A composition comprising at least one sulfonylurea of the formula I wherein R1 is substituted alkyl; halogen; a group ER6 (E=O, S or NR7); COOR8; NO2; S(O)oR9; SO2NR10R11; or CONR10R11; R2 is hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkoxy, haloalkyl, alkylsulfonyl, nitro, cyano or alkylthio; R3 is F, CF3, CF2Cl, CF2H, OCF3, OCF2Cl, or, if R1 is CO2CH3 and R2 is simultaneously fluorine, R3 is Cl, or, if R1 is CH2CF3 or CF2CF3, R3 is methyl, or, if R4 is OCF3 or OCF2Cl, R3 is OCF2H or OCF2Br; R4 is alkoxy, alkyl, alkylthio, alkylamino, dialkylamino, halogen, haloalkyl or haloalkoxy; and R5 is hydrogen, alkoxy or alkyl; or an enviromentally compatible salt of I, and an aryloxyalkanoic acid selected from the group consisting of 2,4-D, 2,4-DB, clomeprop, dichlorprop, dichlorprop-P, dichlorprop-P (2,4-DP-P), fenoprop (2,4,5-TP), fluoroxypyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napropanilide, triclopyr, and an enviromentally compatible salt thereof exhibits a synergistic herbicidal effect.
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(2008/06/13)

Agrochemical formulations for water surface application
New agrochemical formulations for application to the water of paddy fields, which formulations comprise A) at least one solid core material having an apparent specific density of less than 1 and a particle diameter within the range from about 300 μm to about 1,400 μm, and B) a coating layer comprising at least one biologically active compound, at least one substance having the ability to reduce the interfacial tension between water and air, at least one oily substance and, if appropriate, one or more additives, and the use of such agrochemical formulations for applying biologically active compounds to the water of paddy fields.
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(2008/06/13)

Sulphonylaminophenyluracil herbicides for paddy field
A herbicide for paddy field comprising sulphonylaminophenyluracil derivative as an active ingredient which is represented by the formula (I): STR1 wherein R1 represents hydrogen or methyl, R2 represents C1-5 alkyl, fluro-substituted C1-2 alkyl or C3-6 cycloalkyl, optionally applied in combination with another herbicide.
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(2008/06/13)

Herbicidal tetrazolinones
Novel herbicidal tetrazolinones of the formula STR1 wherein Y is hydrogen, bromine or methyl, R1 is ethyl or n-propyl, and R2 is cyclopentyl or cyclohexyl, with the proviso that the total number of carbon atoms in R1 and R2 is 7 or 8. The new tetrazolinones may be mixed with other herbicides.
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(2008/06/13)

Novel synthesis of S-alkyl thiocarbamates from amines, carbon monoxide, elemental sulfur, and alkyl halides in the presence of a selenium catalyst
Carbonyl selenide easily reacted with elemental sulfur at low temperature to form carbonyl sulfide in a good yield, and reaction of ammonium salts of selenocarbamates with elemental sulfur brought about ready transformation to those of thiocarbamates. On the basis of the high catalytic activity of selenium for carbonylation of amines with carbon monoxide in addition to these important findings, a convenient new method for synthesis of S-alkyl thiocarbamates was developed through the carbonylation of amines with carbon monoxide and elemental sulfur in the presence of a selenium catalyst under mild conditions followed by alkylation of ammonium salts of the thiocarbamates with alkyl halides.
Mizuno, Takumi,Nishiguchi, Ikuzo,Sonoda, Noboru
p. 5669 - 5680
(2007/10/02)

Triazolecarboxamide herbicides
Compounds of the formula: STR1 wherein X is O or S; R and R1 are substituted or unsubstituted alkyl, alkenyl, alkynyl or cycloalkyl or R and R1 may be joined to form a heterocyclic ring; R2 is substituted or unsubstituted cycloalkyl; and n is 0, 1 or 2 are disclosed as well as their postemergence and preemergence selective herbicide use against both monocot and dicot weeds in crops such as sugarbeets, cotton, soybeans and rice.
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(2008/06/13)

Herbicidal tetrazolinones
Herbicidal novel tetrazolinones of the formula STR1 wherein Y represents hydrogen, chlorine, or methyl, R1 represents ethyl or n-propyl, and R2 represents cyclopentyl or cyclohexyl, with the proviso that the total of the carbon atoms of R1 and R2 is 7 or 8. They may be mixed with other herbicides.
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(2008/06/13)

Tetrzolinone herbicides
Novel tetrazolinones of the formula (I) STR1 wherein X is chlorine or bromine, Y is hydrogen, chlorine, bromine, methyl or ethyl, and R1 and R2 are the same or different C2-4 alkyl, a process for their preparation, and the use of the new compounds as herbicides, especially against paddy-weeds.
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(2008/06/13)

Facile synthesis of S-alkyl thiocarbamates through reaction of carbamoyl lithium with elemental sulfur
Efficient synthesis of S-alkyl thiocarbamates was developed. The key step of this synthetic method is a conversion of carbamoyl lithium, generated from lithium dialkylamide and carbon monoxide, to lithium thiocarbamate by addition of elemental sulfur.
Mizuno, Takumi,Nishiguchi, Ikuzo,Okushi, Tsuneo,Hirashima, Tsuneaki
p. 6867 - 6868
(2007/10/02)

Benzhydryl compounds as herbicide antidotes
Acids, esters, amides and salts of benzhydryl compounds are antidotes for thiocarbamate and acetamide herbicides. These antidote compounds are especially effective to safen acetamide herbicides used to control grassy weeds and broadleaf weeds in rice, sorghum, corn and wheat.
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(2008/06/13)

Die selenkatalysierte Synthese von S-Alkylthiocarbamaten aus Aminen, Kohlenmonoxid, Schwefel und Alkylhalogeniden
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Sonoda, Noboru,Mizuno, Takumi,Murakami, Sinkichi,Kondo, Kiyoshi,Ogawa, Akiya,at al.
p. 476 - 477
(2007/10/02)

Oxime ethers as herbicidal safeners
The invention relates to novel oxime ethers of the formula I STR1 wherein R1 is hydrogen, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, lower alkylthio, lower haloalkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower haloalkylsulfinyl, lower haloalkylsulfonyl or nitro, each of R2 and R3 is hydrogen, halogen, lower alkyl, lower alkoxy or lower haloalkoxy, and Q is an unsubstituted or substituted lower alkyl, lower alkenyl, lower alkynyl or cycloalkyl group, a lower alkanoyl radical, an aliphatic, cycloaliphatic, aromatic or heterocyclic acyl radical which may be substituted or unsubstituted, a carbonyl or thiocarbonyl radical, an aryl or aralkyl radical, an acylimidomethyl radical, a phthalimidomethyl radical or a heterocyclic radical. These compounds are able to act as antidotes or safeners for protecting cultivated plants from the phytotoxic action of aggressive herbicides. Preferred crops are sorghum, cereals, maize and rice, and herbicides are chiefly chloroacetanilides and thiocarbamates.
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(2008/06/13)

Oxime ethers, the preparation thereof, compositions containing them and use thereof
The invention relates to oxime ethers of the formula I STR1 wherein n is 1 or 2, each of R1 and R2 is hydrogen or C1 -C4 alkyl each of R3 and R4 is hydrogen, halogen, C1 -C4 alkyl, C1 -C4 haloalkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 haloalkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, C1 -C4 haloalkylsulfinyl, C1 -C4 haloalkylsulfonyl or nitro; each of R5 and R6 independently of the other is hydrogen, C1 -C4 alkyl, C1 -C4 haloalkyl, phenyl or phenyl which is substituted by halogen, C1 -C4 alkyl, C1 -C4 haloalkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, carboxyl, carbamoyl, C 1 -C4 alkylcarbamoyl, nitro or cyano, or R5 and R6 together are also a 2- to 6-membered alkylene or alkenylene chain which may be substituted by C1 -C4 alkyl radicals; X is hydrogen, cyano, nitro, chlorine, C1 -C4 alkyl, C1 -C4 haloalkyl, C3 -C6 cycloalkyl, carboxyl, carbamoyl, C1 -C4 alkylcarbonyl, C1 -C4 alkoxycarbonyl or C1 -C4 alkylcarbamoyl. The oxime ethers of the formula I are able to act as antidotes or safeners to protect cultivated plants from the phytotoxic effects of herbicides. Such cultivated plants are preferably sorghum, cereals, maize and rice.
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(2008/06/13)

Synergistic herbicidal compositions and method
A synergistic herbicidal composition comprising a mixture of, (a) an herbicidally effective amount of a thiolcarbamate of the formula, in which X is hydrogen, chlorine or bromine; and R1 and R2 are independently selected from the group consisting of C1-C6 alkyl and C5-C7 cycloalkyl, and (b) an herbicidally effective amount of a propionic acid derivative compound having the formula, wherein R3 is hydrogen or an agriculturally acceptable salt-forming cation selected from the group consisting of diethanolamine, diethylamine, dimethylamine, sodium and potassium; at a weight ratio of (a) to (b) of from about 1:1 to about 4:1.
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(2008/06/13)

Haloacylaminoalkylphosphonates
When applied as safeners, the haloacylaminoalkylphosphinates, haloacylaminoalkylphosphinates and haloacylaminoalkylphosphine oxides of the formula I below are able to protect cultivated plants from the phytotoxic effects of herbicides. Suitable crops are preferably sorghum, cereals, rice, maize and soya beans and the herbicides employed are chloroacetanilides and thiocarbamates. The haloacylaminoalkylphosphonates, haloacylaminoalkylphosphinates and haloacylaminoalkylphosphine oxides have the formula I STR1 wherein R1 is C1 -C4 alkyl, C1 -C4 alkoxy, C2 -C4 alkenyloxy, C2 -C4 alkynyloxy, C1 -C4 haloalkyl, C2 -C8 alkoxyalkoxy or C1 -C4 cyanoalkoxy, R2 is hydrogen or a substituent as defined for R1, R3 and R4 are each independently hydrogen, C1 -C4 alkyl or one of R3 and R4 is also a radical STR2 or both taken together with the carbon atom to which they are attached are also a C3 -C11 cycloalkyl radical, R5 is hydrogen, C1 -C4 alkyl, C3 -C7 cycloalkyl, C2 -C4 alkenyl, C2 -C4 alkynyl, C2 -C8 alkoxyalkyl, C1 -C4 haloalkoxy or aralkyl, R6 is hydrogen or C1 -C4 alkyl, X1 and X2 are each independently halogen or one of X1 and X2 is also hydrogen, and n is 1, 2 or 3.
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(2008/06/13)

Novel oxime ethers, the preparation thereof, compositions containing them and the use thereof
The invention relates to novel oxime ethers of the formula I STR1 wherein R1 is hydrogen, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, lower alkylthio, lower haloalkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower haloalkylsulfinyl, lower haloalkylsulfonyl or nitro, each of R2 and R3 is hydrogen, halogen, lower alkyl, lower alkoxy or lower haloalkoxy, and Q is an unsubstituted or substituted lower alkyl, lower alkenyl, lower alkynyl or cycloalkyl group, a lower alkanoyl radical, an aliphatic, cycloaliphatic, aromatic or heterocyclic acyl radical which may be substituted or unsubstituted, a carbonyl or thiocarbonyl radical, an aryl or aralkyl radical, an acylimidomethyl radical, a phthalimidomethyl radical or a heterocyclic radical. These compounds are able to act as antidotes or safeners for protecting cultivated plants from the phytotoxic action of aggressive herbicides. Preferred crops are sorghum, cereals, maize and rice, and herbicides are chiefly chloroacetanilides and thiocarbamates.
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(2008/06/13)

Oxime ethers, compositions containing them and the use thereof
The oxime ethers of the formula I below are able to act as antidotes or safeners to protect cultivated plants from the phytotoxic effects of herbicides. Such cultivated plants are preferably sorghum, cereals, maize and rice, and herbicides are principally chloroacetanilides and thiocarbamates. The oxime ethers have the formula I STR1 wherein n is 1 or 2, each of R1 and R2 is hydrogen or C1 -C4 alkyl each of R3 and R4 is hydrogen, halogen, C1 -C4 alkyl, C1 -C4 haloalkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 haloalkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, C1 -C4 haloalkylsulfinyl, C1 -C4 haloalkylsulfonyl or nitro; each of R5 and R6 independently of the other is C1 -C4 alkyl, C1 -C4 haloalkyl, C2 -C8 alkoxyalkyl, C3 -C4 alkenyl, C3 -C4 alkynyl, or together form a 2- to 6-membered alkylene or alkenylene bridge which may be substituted by 1 to 4 C1 -C4 alkyl, C1 -C4 haloalkyl, C1 -C4 alkoxy, C2 -C4 alkenyloxy, C2 -C8 alkoxyalkyl or C3 -C8 alkenyloxyalkyl groups; each of A and B independently of the other is oxygen or sulfur, or one of A and B is the methine group, X is a fluorinated C1 -C3 alkyl radical which may also additionally contain chlorine, and Y is hydrogen, C1 -C4 alkyl, C1 -C4 haloalkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy or phenyl.
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(2008/06/13)

Furanyl oximes
Novel oxime ethers and oxime esters of the formula I given herein have various advantageous effects with regard to stimulation of plant growth, particularly in the early stage of development of the plant. Furthermore, such compounds have the property of rendering, in the sense of an antidote action, agricultural chemicals which would otherwise damage the plants (phytotoxic chemicals) more compatible with the cultivated plants. Herbicides that are insufficiently selective can be used for example in the presence of such oxime derivatives in specific cultivated crops for combating weeds, without disadvantageous consequences for the cultivated plants.
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(2008/06/13)

Herbicidal sulfonamides
This invention relates to benzylsulfonylureas which are active pre- and post-emergence herbicides.
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(2008/06/13)

Phase-Transfer-Catalysed Preparation of S-Alkyl Thiocarbamates
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Chin-Hsien, Wang
p. 622 - 623
(2007/10/02)

Phenylglyoxylonitrile-2-oxime-cyanomethyl ether as plant growth regulator
Phenylglyoxylonitrile-2-oxime-cyanomethyl ether of the formula STR1 and compositions containing it, have various advantageous effects with regard to regulation of plant growth. Furthermore, this compound and its compositions have the property of rendering, in the sense of an antidote (safening) action, agricultural chemicals which would otherwise damage the plants more compatible with cultivated plants. Strong herbicides, for example chloroacetanilides or thiolcarbamates, can be used in the presence of such safening agents in specific crops such as sorghum and rice for combatting weeds without disadvantageous consequences for the crops. The safeners are preferably applied to the crop seeds prior to planting.
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(2008/06/13)

Thiocarbamate preparation utilizing quaternary ammonium salt catalysts
Thiocarbamates are prepared by a process comprising reacting an aqueous solution of a thiocarbamate salt with an organic halide in the presence of a catalytic amount of a quaternary ammonium salt having the formula in which R4 and R5 are independently selected from the group consisting of C1 -C25 alkyl and C2 -C25 alkenyl, R6 and R7 are independently selected from the group consisting of C6 -C25 alkyl and C6 -C25 alkenyl, and Y- is an anion selected from the group consisting of chloride and bromide; and separating the thiocarbamate from the aqueous solution.
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(2008/06/13)

Process for preparing a thiolcarbamate
Thiolcarbamates are prepared by reacting a secondary amine having the formula EQU1 wherein R1 and R2 are the same or different and each represent hydrogen, lower alkyl, alkoxy, alkenyl, alkoxyalkyl, cycloalkyl, hydroxyalkyl, benzyl or phenyl or R1 and R2 combined is a nitrogen containing heterocyclic ring with carbonylsulfide to form an intermediate of an amine salt of a thiolcarbamic acid having the formula EQU2 wherein R1 and R2 are defined as above, in an organic solvent having the formula SPC1 Wherein n is 0, 1 or 2 and R' is hydrogen, halogen or a lower alkyl group which solvent is sparingly soluble or insoluble in water and which dissolves the amine salt of the thiolcarbonic acid, and then reacting the intermediate with an alkyl halide having the formula wherein X represents halogen, and R3 represents hydrogen, lower alkyl or naphthyl or phenyl which can be substituted with halogen, alkyl, alkoxy, alkylthio, cyano or nitro, to yield a thiolcarbamate having the formula EQU3
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(2008/06/13)