2008-41-5

Usage

Uses

Used in Agriculture:
Butylate is used as a herbicide for controlling grassy and broadleaf weeds and seeds in the soil prior to sowing a crop. It is a selective herbicide for use on field corn, sweet corn, and popcorn. It is often applied in combination with atrazine and/or cyanazine.
Note: Butylate is not approved for use in EU countries.

Trade name

ANELDA PLUS?; ANELDAZIN?; ANELIROX?; ATRA-BUTE?[C] Nov.1992; BUTILATE?; GENATE?[C] August 1994; R-1910?[C] Dec.1987; STAUFFER R-1910?[C] Dec.1987; SUTAN?[C] Sept.1994; SUTAZINE?[C] Dec.1987; TOMAHAWK?

Potential Exposure

A thiocarbamate herbicide. A potential danger to those involved in the manufacture, formulation or application of this carbamate herbicide which is used to control weed seeds in the soil prior to sowing crops

Incompatibilities

Thiocarbamate esters are combustible. They react violently with powerful oxidizers such as calcium hypochlorite. Poisonous gases are generated by the thermal decomposition of thiocarbamate compounds, including carbon disulfide, oxides of sulfur, oxides of nitrogen, hydrogen sulfide, ammonia, and methylamine. Many materials in this group slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids. Flammable gases are generated by the combination of thiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates are incompatible with acids, peroxides, and acid halides

InChI:InChI=1/C11H23NOS/c1-6-14-11(13)12(7-9(2)3)8-10(4)5/h9-10H,6-8H2,1-5H3

Upstream product

• 38952-42-0 diisobutylcarbamic acid chloride 
• 811-51-8 sodium thioethylate 
• 64-67-5 diethyl sulfate 

Downstream Products

• 51892-57-0 S-ethyl diisobutylthiocarbamate S,S-dioxide 
• 78-81-9 isobutylamine 

Relevant academic research and scientific papers

Soluble polymer based matrix for chemically active water insoluble components

This invention relates to a water soluble matrix composition comprising an anionic surfactant, a C6 to C18 alkyl pyrrolidone, urea and a water insoluble copolymer of vinyl pyrrolidone with not more than 50 wt. % of a comonomer selected from the group of an α-olefin, vinyl acetate, an acrylic or methacrylic acid ester and methacrylamide as a free flowing particulate solid which matrix is suitably mixed with a water insoluble, chemically active component, such as an agrochemical, to provide a clear sprayable film forming emulsion, such as a non-leachable film on a plant or other substrate surface. The invention also relates to the method of preparing the matrix and to the incorporation of an agrochemical concentrate and plant spray composition.

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.

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.

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.

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.

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.

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.

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.

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.

Process for the preparation of substituted S-alkyl thio-carbamates

The invention relates to a new and advantageous process for the preparation of substituted S-alkyl thiocarbamates having the general formula (I), EQU1 wherein R1 stands for a C1-4 alkyl group, R2 stands for a C1-4 alkyl or cyclohexyl group, or R1 and R2 may form together a C4-6 polymethylene group, and R3 stands for a C2-3 alkyl group. In accordance with the invention the substituted O-alkyl thiocarbamates of the general formula (II), EQU2 wherein R1, R2 and R3 each have the same meanings as defined above, are subjected to isomerization by heating them at a temperature of 130° to 180°C in the presence of dimethyl sulfate or diethyl sulfate to yield the appropriate S-alkyl esters.