2444-96-4

Upstream product

• 13358-73-1 N,N-dibutylcarbamoyl chloride 
• 811-51-8 sodium thioethylate 

Relevant academic research and scientific papers

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.

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.

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.