Abstract: N-haloacyl oxazolidines substituted in the 5-position with oxy or thio containing groups as new compositions of matter useful as active herbicidal antidotes to protect against and decrease crop injury when used with thiolcarbamate herbicides, and when applied in various methods; improved herbicidal compositions and utility of said compositions to protect against and decrease phytotoxic injury to crops when employing thiolcarbamate herbicides and a two-part herbicide system consisting essentially of a first-part of one or more thiolcarbamate herbicides and a second part of an effective antidote compound therefor, said antidote compounds of the class 3-haloacyl oxazolidine having the formula ##STR1## wherein X is selected from the group consisting of oxygen and sulfur; R.sub.1 is selected from the group consisting of alkyl and alkenyl; R is selected from the group consisting of haloalkyl, alkylthio and p-tolylsulfonamido; R.sub.2 and R.sub.

Abstract: A 2-iminophenyl thiazolidine having the formula ##STR1## wherein R is hydrogen or methyl; R.sub.1 is halo, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, perhalomethyl, difluoromethyl, pentafluoroethyl, trifluoromethylthhio, difluoromethoxy, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl, C.sub.1 -C.sub.4 alkyloxyiminomethyl, benzyloxyiminomethyl, 1-(C.sub.1 -C.sub.4 alkyl)-oxyiminoethyl or 1-benzyloxyiminoethyl; R.sub.2 is hydrogen or halo; R.sub.3 and R.sub.4 are independently hydrogen, halo, nitro, cyano, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 fluoroalkoxy, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; and X is hydrogen or halogen.Also disclosed is a process for making the compounds and a method of use which comprises applying the compound or composition to the locus where control is desired.

Abstract: An oxazolidine having the formula ##STR1## wherein R is selected from the group consisting of alkyl, substituted alkyl, alkenyl, cycloalkyl, benzyl, alkoxyalkyl, carboalkoxyalkyl, alkylthioalkyl, phenyl, substituted phenyl, furanyl, phenoxyalkyl, carboalkoxy, substituted phenoxyalkyl, alkylamino, alkoxy, chloroethylamino, alkylthio, cycloalkylalkyl, cycloalkenylalkyl, phenylamino, substituted phenylamino, alkenylamino, and benzylamino; Z is selected from the group consisting of oxygen or sulfur; R.sub.1 is selected from the group consisting of alkyl or halosubstituted alkyl wherein the alkyl group has from 1 to 4 carbon atoms; and X and Y are the same or different and are selected from the group consisting of trifluoromethyl, chloro, bromo, fluoro, hydrogen, cyano, alkyl, thioalkyl, halothioalkyl, alkoxy and sulfonylalkyl, wherein the alkyl groups in each alkyl-containing moiety have from 1 to 4 carbon atoms. Also disclosed is a method of use.

Abstract: Dichloroacetamidines having the formula ##STR1## in which A and B are independently selected from hydrogen, fluorine, chlorine, bromine and methyl, provided that at least one of A or B is other than hydrogen;M is hydrogen or methyl;X is selected from the group consisting of trifluoromethyl, lower alkyl, nitro, chloro, bromo, fluoro, cyano, lower alkoxy acetyl, lower alkylthio, trifluoromethylthio, and 3,3-diloweralkyl ureido;Y is selected from the group consisting of hydrogen, lower alkyl, chloro, fluoro, nitro, trifluoromethyl, and lower alkoxy;Z is selected from the group consisting of hydrogen and chloro;R.sub.1 is selected from the group consisting of hydrogen, alkyl and allyl;R.sub.2 is selected from the group consisting of alkyl, allyl, benzyl, hydroxyalkyl, alkynyl, N-alkyl amido, alkoxyalkyl, dialkoxyalkyl, alkoxy, cyano alkyl, substituted phenyl wherein the substituent is selected from the group trifluoromethyl, dichloro and 3,3-dimethylureido; andR.sub.1 and R.sub.

Abstract: An imidazolidine-2-one having the formula ##STR1## in which X, X', Y and Y' are the same or different and are selected from the group consisting of trifluoromethyl, chloro, bromo, fluoro, hydrogen, cyano, alkyl, thioalkyl, halothialkyl, alkoxy and sulfonylalkyl, wherein the alkyl groups have from one to four carbon atoms; andR is selected from the group consisting of hydrogen and alkyl wherein the alkyl groups have from one to four carbon atoms. The compounds are useful as herbicidal agents.

Abstract: An oxazolidine having the formula ##STR1## wherein X, Y, X' and Y' are the same or different and are selected from the group consisting of hydrogen, chloro, bromo, fluoro, trifluoromethyl, m-trifluoromethylphenoxy, methyl, methylthio, methoxy, cyano, nitro and methylsulfonyl; and R is selected from the group consisting of methyl ethyl, chloromethyl and hydroxy methyl.

Abstract: Novel S-benzyl thiolcarbamates are disclosed, having the formula ##STR1## in which R.sup.1 is selected from the group consisting of hydrogen and methoxy,R.sup.2 is selected from the group consisting of methyl, ethyl, and allyl, andR.sup.3 is selected from the group consisting of straight-chain C.sub.3 -C.sub.6 alkyl optionally substituted with one or two methyl groups, and allyl.The compounds are particularly effective in the control of weeds associated with rice crops.

Abstract: Dichloroacetamidines having the formula ##STR1## in which A and B are independently selected from hydrogen, fluorine, chlorine, bromine and methyl, provided that at least one of A or B is other than hydrogen;M is hydrogen or methyl;X is selected from the group consisting of trifluoromethyl, lower alkyl, nitro, chloro, bromo, fluoro, cyano, lower alkoxy acetyl, lower alkylthio, trifluoromethylthio, and 3,3-diloweralkyl ureido;Y is selected from the group consisting of hydrogen, lower alkyl, chloro, fluoro, nitro, trifluoromethyl, and lower alkoxy;Z is selected from the group consisting of hydrogen and chloro;R.sub.1 is selected from the group consisting of hydrogen, alkyl and allyl;R.sub.2 is selected from the group consisting of alkyl, allyl, benzyl, hydroxyalkyl, alkynyl, N-alkyl amido, alkoxyalkyl, dialkoxyalkyl, alkoxy, cyano alkyl, substituted phenyl wherein the substituent is selected from the group trifluoromethyl, dichloro and 3,3-dimethylureido; andR.sub.1 and R.sub.

Abstract: A substituted oxazolidone compound having the formula ##STR1## wherein Ar.sup.1 and Ar.sup.2 are the same or different and are aromatic or a substituted aromatic group wherein the substituent is selected from chlorine, bromine, chloride or trifluoromethyl, and R is lower alkyl having from 1 to 6 carbon atoms.

Abstract: Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines useful as active antidotes against crop injury when used with various herbicides; herbicidal compositions and utility of various herbicides and aryl substituted oxazolidines and thiazolidines having the formula ##STR1## wherein X and Y are independently oxygen or sulfur; R is haloalkyl or chloroalkenyl; R.sub.1 is hydrogen, lower alkyl, phenyl, naphthyl, substituted phenyl wherein said substituents are monofluoro, mono- or di- chloro, nitro, methyl, methoxy, or hydroxyl; R.sub.2 is hydrogen or lower alkyl; R.sub.3 is hydrogen, lower alkyl, hydroxymethyl, N-methyl carbamoyloxymethyl or dichloroacetoxymethyl; R.sub.4 is hydrogen or lower alkyl; R.sub.5 is hydrogen, lower alkyl or phenyl; and R.sub.6 is hydrogen; provided that at least one of R.sub.1 or R.sub.5 is phenyl, substituted phenyl or naphthyl.

Abstract: Compounds defined by the generic formula ##STR1## wherein R is selected from the group consisting of C.sub.1 -C.sub.6 alkyl including methyl, ethyl, propyl, butyl, pentyl and hexyl, preferably C.sub.2 -C.sub.4 alkyl including ethyl, propyl and butyl, C.sub.1 -C.sub.3 alkylthio including methylthio, ethylthio and propylthio, preferably methylthio and pentafluoroethyl; R.sub.1 is selected from the group consisting of hydrogen, methyl and ethyl, preferably methyl; m is 0 or 1; and n is 1 or 2, exhibit herbicidal activity.

Abstract: A compound having the structural formula ##STR1## wherein R is hydrogen or C.sub.1 -C.sub.3 alkyl, preferably methyl;R.sup.1 is C.sub.1 -C.sub.3 alkyl, preferably ethyl; andR.sup.2 is C.sub.1 -C.sub.3 alkyl, preferably ethyl; C.sub.1 -C.sub.2 alkylamino, preferably methylamino; C.sub.2 -C.sub.4 dialkylamino, preferably dimethylamino; or C.sub.2 -C.sub.4 alkylalkoxyamino, preferably methylmethoxyamino; and its use as a post-emergent herbicide.

Abstract: 1-(Substituted phenylthiocarbamyl) 3,3-disubstituted formamidine compounds having the structural formula ##STR1## wherein n is 1, 2 or 3,R is alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogen, nitro, acyl having 1 to 4 carbon atoms, hydroxyl and ##STR2## wherein R.sup.3 and R.sup.4 have the same meaning as R.sup.1 and R.sup.2 defined below,R.sup.1 and R.sup.2 are the same or different and are alkyl having 1 to 6 carbon atoms, or taken together represent the chain --(CH.sub.2).sub.p --(X).sub.m --(CH.sub.2).sub.q and forming a ring structure with the nitrogen to which they are bound wherein p is 1, 2 or 3, q is 2 or 3, X represents --O--, --S--, --SO--, --SO.sub.2 --, --NR.sup.3 --, R.sup.3 is hydrogen or alkyl having 1 to 6 carbon atoms, and m is 0 or 1 and their use as pharmaceutical agents.

Abstract: A compound having the structural formula ##STR1## wherein R is selected from the group consisting of C.sub.1 -C.sub.5 alkyl, preferably methyl; C.sub.1 -C.sub.3 haloalkyl, preferably C.sub.2 -haloalkyl and most preferably trifluoromethyl; aryl, preferably phenyl, C.sub.2 -C.sub.8 alkoxyalkyl, preferably ethoxyethyl and ethoxyethoxyethyl;R' is selected from the group consisting of C.sub.2 -C.sub.8 alkyl, preferably C.sub.2 -C.sub.3 alkyl; C.sub.1 -C.sub.3 alkoxy, preferably methoxy; cyclopropyl; methacryl; C.sub.1 -C.sub.3 alkylmercapto, preferably methylmercapto; methylamino; ethylamino; C.sub.2 -C.sub.4 dialkylamino, preferably dimethylamino; C.sub.2 -C.sub.4 alkylalkoxyamino, preferably methylmethoxyamino; andn equals the integer 0 or 1.

Abstract: A compound having the structural formula ##STR1## wherein R is selected from the group consisting of hydrogen and C.sub.1 -C.sub.3 alkyl ammonium; R' is selected from the group consisting of C.sub.2 -C.sub.8 alkyl, C.sub.1 -C.sub.3 alkoxy, cyclopropyl, methacryl, C.sub.1 -C.sub.3 alkylmercapto, methylamino, ethylamino, C.sub.2 -C.sub.4 dialkylamino, C.sub.2 -C.sub.4 alkylalkoxyamino; and n equals the integer 0 or 1; and its use as a herbicide and as a herbicide intermediate.

Abstract: Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines useful as active antidotes against crop injury when used with various herbicides; herbicidal compositions and utility of various herbicides and aryl substituted oxazolidines and thiazolidines having the formula ##STR1## wherein X and Y are independently oxygen or sulfur; R is haloalkyl or chloroalkenyl; R.sub.1 is hydrogen, lower alkyl, phenyl, naphthyl, substituted phenyl wherein said substituents are monofluoro, mono- or di- chloro, nitro, methyl, methoxy, or hydroxy; R.sub.2 is hydrogen or lower alkyl; R.sub.3 is hydrogen, lower alkyl, hydroxymethyl, N-methyl carbamoyloxymethyl or dichloroacetoxymethyl; R.sub.4 is hydrogen or lower alkyl; R.sub.5 is hydrogen, lower alkyl or phenyl; and R.sub.6 is hydrogen; provided that at least one of R.sub.1 or R.sub.5 is phenyl, substituted phenyl or naphthyl.

Abstract: Herbicide antidote compounds and herbicidal compositions consisting of an active herbicide compound and an antidote therefore and the methods of use of the antidote compound and compositions wherein the antidote compounds correspond to the formula ##STR1## in which R is dialkylaminoalkyl having from 3 to 9 carbon atoms, inclusive.

Abstract: Compounds having the formula ##STR1## in which R is selected from the group consisting of chloro and fluoro;R.sub.1 -R.sub.4 are each independently selected from the group consisting of hydrogen and 1-4 carbon alkyl; andX is oxygen or sulfur protect crops from thiocarbamate herbicidal injury.

Abstract: Herbicide antidote compounds and herbicidal compositions consisting of at least one active thiolcarbamate herbicide compound and an antidote therefor and the methods of use of the antidote compound and compositions wherein the antidote compounds correspond to the formula ##STR1## wherein R is haloalkyl having 1-4 carbon atoms, inclusive, and n is 2 or 3.

Abstract: Compounds defined by the generic formula ##STR1## wherein R is hydrogen or hydroxyl, R.sub.1 is selected from the group consisting of methyl and hydrogen; R.sub.2 is selected from the group consisting of C.sub.1 -C.sub.4 alkyl including methyl, ethyl, propyl and butyl and methoxy; R.sub.3 is selected from the group consisting of hydrogen, methyl and ethyl; m is 0 or 1; and n is 1 or 2, exhibit herbicidal activity.