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US 5,424,333 AGranted
Anthelmintic N'-substituted-N,N'-disubstitutedhydrazines
AssigneeRohm and Haas Company
InventorKeith D. Wing
Life of this patent
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Abstract
This invention relates to the anthelmintic use of compositions containing N'-substituted-N,N'-disubstitutedhydrazines. Specifically, the invention relates to methods of controlling helminths by contacting the helminths with a compound having a nucleus of the formula ##STR1## wherein X and X' are the same or different O, S, or NR and A', B', R.sup.1 and R.sup.2 are a variety of substituents.
Claims14
A method of controlling helminths which comprises contacting the helminths with a compound having the formula ##STR59## wherein X and X' are the same or different O, S or NR;
- R.sup.1 is unsubstituted (C.sub.3 -C.sub.10) branched alkyl or (C.sub.1 -C.sub.10)alkyl substituted with one to four of the same or different (C.sub.3 -C.sub.6)cycloaklyl, fluoro, straight chain (C.sub.2 -C.sub.4)alkenyl, carboxyl, (C.sub.1 -C.sub.3)alkoxycarbonyl, cyano, cyano substituted (C.sub.1 -C.sub.4)alkyl, tri(C.sub.1 -C.sub.4 alkylsilyl having independently the stated number of carbon atoms in each alkyl group or tri(C.sub.1 -C.sub.2)alkylsilylmethyl having independently the stated number of carbon atoms in each alkyl group;
- R.sup.2 is hydrogen;
- (C.sub.1 -C.sub.6)alkyl;
- (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl having independently the stated number of carbon atoms in each alkyl group;
- (C.sub.1 -C.sub.6)alkylthio(C.sub.1 -C.sub.6)alkyl having independently the stated number of carbon atoms in each alkyl group;
- (C.sub.2 -C.sub.6)alkenyl;
- (C.sub.2 -C.sub.6)alkynyl or phen(C.sub.1 -C.sub.4)alkyl where the phenyl ring is unsubstituted or substituted with one to three of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, halo(C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, halo(C.sub.1 -C.sub.4)alkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkyl amino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- and
- A' and B' are the same or different unsubstituted naphthyl or substituted naphthyl where the substituents can be from one to three of the same or different halo;
- cyano;
- nitro;
- hydroxy;
- (C.sub.1 -C.sub.4)alkoxy;
- (C.sub.1 -C.sub.4)alkyl;
- carboxy;
- (C.sub.1 -C.sub.4)alkoxycarbonyl;
- (C.sub.1 -C.sub.4)alkanoyloxy;
- amino;
- (C.sub.1 -C.sub.4)alkylamino;
- or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- or unsubstituted phenyl or substituted phenyl where the substituents can be from one to five of the same or different halo;
- nitro;
- cyano;
- hydroxy;
- (C.sub.1 -C.sub.6)alkyl;
- (C.sub.1 -C.sub.6)haloalkyl;
- (C.sub.1 -C.sub.6)cyanoalkyl;
- (C.sub.1 -C.sub.6)hydroxyalkyl;
- (C.sub.1 -C.sub.6)alkoxy;
- (C.sub.1 -C.sub.6)haloalkoxy;
- (C.sub.1 -C.sub.6)epoxialkyl;
- (C.sub.1 -C.sub.6)alkoxyalkyl having independently the stated number of carbon atoms in each alkyl group;
- (C.sub.1 -C.sub.6)alkoxyalkoxy having independently the stated number of carbon atoms in each alkyl group;
- carboxyoxy;
- (C.sub.1 -C.sub.6)alkylthioalkoxy having independently the stated number of carbon atoms in each alkyl group;
- (C.sub.1 -C.sub.6)alkanoyloxyalkyl having independently the stated number of carbon atoms in each alkyl group;
- (C.sub.1 -C.sub.6)alkoxycarbonyloxy;
- (C.sub.2 -C.sub.6)alkenyl optionally substituted with halo, cyano, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)haloalkoxy or (C.sub.1 -C.sub.4)alkylthio;
- carboxy;
- (C.sub.1 -C.sub.6)carboxyalkyl;
- (C.sub.1 -C.sub.6)alkoxycarbonylalkyl having independently the stated number of carbon atoms in each alkyl group;
- --COR;
- (C.sub.1 -C.sub.6)haloalkylcarbonyl;
- (C.sub.1 -C.sub.6)cyanoalkylcarbonyl;
- (C.sub.1 -C.sub.6)nitroalkylcarbonyl;
- (C.sub.1 -C.sub.6)alkoxycarbonyl;
- (C.sub.1 -C.sub.6)haloalkoxycarbonyl;
- alkanoyloxy;
- amino;
- (C.sub.1 -C.sub.6)alkylamino;
- (C.sub.1 -C.sub.6)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- amino or (C.sub.1 -C.sub.6)alkylamino where the N of the amino or (C.sub.1 -C.sub.6)alkylamino is substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio groups;
- phenylamino;
- diphenylamino;
- --CONRR';
- --OCONRR';
- --C(NR)NR'R";
- --N.dbd.NR;
- --NRCOR';
- --NRCO.sub.2 R';
- --N(COR)COR';
- --OCONRCOR';
- sulfhydryl;
- phenylazo;
- halothio;
- (C.sub.1 -C.sub.6)alkylthio;
- (C.sub.1 -C.sub.6)haloalkylthio;
- (C.sub.1 -C.sub.6)alkylsulfinyl;
- (C.sub.1 -C.sub.6)alkylsulfonyl;
- phenylsulfonyl;
- (C.sub.1 -C.sub.6)alkylsulfonate;
- (C.sub.1 -C.sub.6)haloalkylsulfonyloxy;
- --SO.sub.2 NRR';
- --NRSOR';
- --NRSO.sub.2 R';
- --CSR;
- --CS.sub.2 R;
- --NRCSR';
- --SCOR;
- unsubstituted phenyl;
- phenyl substituted with one to three of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- phenoxy where the phenyl ring is unsubstituted or substituted with one to three of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- phenylthio where the phenyl ring is unsubstituted or substituted with one to three of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- benzoyl where the phenyl ring is unsubstituted or substituted with one to three of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- phenoxycarbonyl where the phenyl ring is unsubstituted or substituted with one to three of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- --CR.dbd.N--R.sup.3 where R.sup.3 is hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, amino, (C.sub.1 -C.sub.4)alkylamino, (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group, phenylamino, --COR, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, benzoyl, phenoxycarbonyl or --CONRR';
- or when two adjacent positions on the phenyl ring are substituted with alkoxy groups, these groups may be joined to form a 5- or 6-membered dioxolano or dioxano heterocyclic ring;
- unsubstituted six-membered heterocycle or substituted six-membered heterocycle having one, two, three or four nitrogen atoms and two to five nuclear carbon atoms where the substituents can be from one to three of the same or different halo;
- nitro;
- hydroxy;
- (C.sub.1 -C.sub.6)alkyl;
- (C.sub.1 -C.sub.6)alkoxy;
- (C.sub.1 -C.sub.6)thioalkoxy;
- carboxy;
- (C.sub.1 -C.sub.6)alkoxycarbonyl;
- (C.sub.1 -C.sub.6)carboxyalkyl;
- (C.sub.1 -C.sub.6)alkoxycarbonylalkyl having independently the stated number of carbon atoms in each alkyl group;
- --CONRR';
- amino;
- (C.sub.1 -C.sub.6)alkylamino;
- (C.sub.1 -C.sub.6)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- --NRCOR';
- (C.sub.1 -C.sub.6)alkylthio;
- unsubstituted phenyl;
- or substituted phenyl having one to three of the same or different halo, nitro, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)haloalkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)haloalkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- unsubstituted or substituted five-membered heterocycle selected from furyl, thienyl, triazolyl, pyrrolyl, isopyrrolyl, pyrazolyl, isoimidazolyl, thiazolyl, isothiazolyl, oxazolyl and isooxazolyl where the substituents can be from one to three of the same or different halo;
- nitro;
- hydroxy;
- (C.sub.1 -C.sub.6)alkyl;
- (C.sub.1 -C.sub.6)alkoxy;
- carboxy;
- (C.sub.1 -C.sub.6)alkoxycarbonyl;
- (C.sub.1 -C.sub.6)carboxyalkyl;
- (C.sub.1 -C.sub.6)alkoxycarbonylalkyl having independently the stated number of carbon atoms in each alkyl group;
- --CONRR';
- amino;
- (C.sub.1 -C.sub.6)alkylamino;
- (C.sub.1 -C.sub.6)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- --NRCOR';
- (C.sub.1 -C.sub.6)alkylthio;
- unsubstituted phenyl;
- or substituted phenyl having one to three of the same or different halo, nitro, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)haloalkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)haloalkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl;
- amino;
- (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- unsubstituted (C.sub.1 -C.sub.10)alkyl or substituted (C.sub.1 -C.sub.10)alkyl having one to four of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- unsubstituted (C.sub.3 -C.sub.8)cycloalkyl or substituted (C.sub.3 -C.sub.8)cycloalkyl having one to four of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)haloalkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)haloalkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- unsubstituted (C.sub.2 -C.sub.8)alkenyl or substituted (C.sub.2 -C.sub.8)alkenyl or unsubstituted (C.sub.3 -C.sub.8)alkadienyl or substituted (C.sub.3 -C.sub.8)alkadienyl having one to four of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.3 -C.sub.6)cycloalkyl, (C.sub.1 -C.sub.4)haloalkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)haloalkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- unsubstituted (C.sub.3 -C.sub.8)cycloalkenyl or substituted (C.sub.3 -C.sub.8)cycloalkenyl or unsubstituted (C.sub.3 -C.sub.8)cycloalkadienyl or substituted (C.sub.3 -C.sub.8)cycloalkadienyl having one to four of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)haloalkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)haloalkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- or unsubstituted (C.sub.2 -C.sub.8)alkynyl or substituted (C.sub.2 -C.sub.8)alkynyl having one to four of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)haloalkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)haloalkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- where R, R' and R" are hydrogen or (C.sub.1 -C.sub.6)alkyl;
- and
- agronomically acceptable salts thereof.
129 more elements
A method of controlling helminths which comprises contacting the helminths with a compound having the formula ##STR60## wherein X and X' are the same or different O, S or NR;
- provided at least one of X and X' is O;
- R.sup.1 is unsubstituted (C.sub.3 -C.sub.10) branched alkyl or (C.sub.1 -C.sub.10)alkyl substituted with one to four of the same or different (C.sub.3 -C.sub.6)cycloalkyl, fluoro, straight chain (C.sub.2 -C.sub.4)alkenyl, carboxyl, (C.sub.1 -C.sub.3)alkoxycarbonyl, cyano, cyano substituted (C.sub.1 -C.sub.4)alkyl, tri(C.sub.1 -C.sub.4)alkylsilyl having independently the stated number of carbon atoms in each alkyl group or tri(C.sub.1 -C.sub.2)alkylsilylmethyl having independently the stated number of carbon atoms in each alkyl group;
- R.sup.2 is hydrogen;
- or (C.sub.1 -C.sub.6)alkyl;
- and
- A and B are the same or different unsubstituted naphthyl or substituted naphthyl where the substituents can be from one to three of the same or different halo;
- cyano;
- nitro;
- hydroxy;
- (C.sub.1 -C.sub.4)alkoxy;
- (C.sub.1 -C.sub.4)alkyl;
- carboxy;
- (C.sub.1 -C.sub.4)alkoxycarbonyl;
- (C.sub.1 -C.sub.4)alkanoyloxy;
- amino;
- (C.sub.1 -C.sub.4)alkylamino;
- or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- or
- unsubstituted phenyl or substituted phenyl where the substituents can be from one to five of the same or different halo;
- nitro;
- cyano;
- hydroxy;
- (C.sub.1 -C.sub.6)alkyl;
- (C.sub.1 -C.sub.6)haloalkyl;
- (C.sub.1 -C.sub.6)cyanoalkyl;
- (C.sub.1 -C.sub.6)hydroxyalkyl;
- (C.sub.1 -C.sub.6)alkoxy;
- (C.sub.1 -C.sub.6)haloalkoxy;
- (C.sub.1 -C.sub.6)epoxialkyl;
- (C.sub.1 -C.sub.6)alkoxyalkyl having independently the stated number of carbon atoms in each alkyl group;
- (C.sub.1 -C.sub.6)alkoxyalkoxy having independently the stated number of carbon atoms in each alkyl group;
- carboxyoxy;
- (C.sub.1 -C.sub.6)alkylthioalkoxy having independently the stated number of carbon atoms in each alkyl group;
- (C.sub.1 -C.sub.6)alkanoyloxyalkyl having independently the stated number of carbon atoms in each alkyl group;
- (C.sub.1 -C.sub.6)alkoxycarbonyloxy;
- (C.sub.2 -C.sub.6)alkenyl optionally substituted with halo, cyano, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)haloalkoxy or (C.sub.1 -C.sub.4)alkylthio;
- carboxy;
- (C.sub.1 -C.sub.6)carboxyalkyl;
- (C.sub.1 -C.sub.6)alkoxycarbonylalkyl having independently the stated number of carbon atoms in each alkyl group;
- --COR;
- (C.sub.1 -C.sub.6)haloalkylcarbonyl;
- (C.sub.1 -C.sub.6)cyanoalkylcarbonyl;
- (C.sub.1 -C.sub.6)nitroalkylcarbonyl;
- (C.sub.1 -C.sub.6)alkoxycarbonyl;
- (C.sub.1 -C.sub.6)haloalkoxycarbonyl;
- alkanoyloxy;
- amino;
- (C.sub.1 -C.sub.6)alkylamino;
- (C.sub.1 -C.sub.6)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- amino or (C.sub.1 -C.sub.6)alkylamino where the N of the amino or (C.sub.1 -C.sub.6)alkylamino is substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio groups;
- phenylamino;
- diphenylamino;
- --CONRR';
- --OCONRR';
- --C(NR)NR'R";
- --N.dbd.NR;
- --NRCOR';
- --NRCO.sub.2 R';
- --N(COR)COR';
- --OCONRCOR';
- sulfhydryl;
- phenylazo;
- halothio;
- (C.sub.1 -C.sub.6)alkylthio;
- (C.sub.1-6)haloalkylthio;
- (C.sub.1 -C.sub.6)alkylsulfinyl;
- (C.sub.1 -C.sub.6)alkylsulfonyl;
- phenylsulfonyl;
- (C.sub.1 -C.sub.6)alkylsulfonate;
- (C.sub.1 -C.sub.6)haloalkylsulfonyloxy;
- --SO.sub.2 NRR';
- --NRSOR';
- --NRSO.sub.2 R';
- --CSR;
- --CS.sub.2 R;
- --NRCSR';
- --SCOR;
- unsubstituted phenyl;
- phenyl substituted with one to three of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- phenoxy where the phenyl ring is unsubstituted or substituted with one to three of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- phenylthio where the phenyl ring is unsubstituted or substituted with one to three of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- benzoyl where the phenyl ring is unsubstituted or substituted with one to three of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- phenoxycarbonyl where the phenyl ring is unsubstituted or substituted with one to three of the same or different halo, cyano, nitro, hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, amino, (C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;
- --CR.dbd.N--R.sup.3 where R.sup.3 is hydroxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, amino, (C.sub.1 -C.sub.4)alkylamino, (C.sub.1 -C.sub.4)dialkylamino having independently the stated number of carbon atoms in each alkyl group, phenylamino, --COR, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkanoyloxy, benzoyl, phenoxycarbonyl or -- CONRR';
- or when two adjacent positions on the phenyl ring are substituted with alkoxy groups, these groups may be joined to form a 5- or 6-membered dioxolano or dioxano heterocyclic ring;
- where R, R' and R" are hydrogen or (C.sub.1 -C.sub.6)alkyl;
- and
- agronomically acceptable salts thereof.
85 more elements
Dependencies are inferred from the claim text.