Claims
- 1. An herbicidal composition comprising
- (a) an herbicidally effective amount of a thiolcarbamate having the formula ##STR17## wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl; phenyl; C.sub.7 -C.sub.9 phenylalkyl; C.sub.3 -C.sub.6 alkenyl; C.sub.3 -C.sub.6 haloalkenyl; or C.sub.7 -C.sub.9 phenylalkyl, mono- or polysubstituted on the phenyl ring with halogen;
- R.sup.2 and R.sup.3 are either selected independently from C.sub.1 -C.sub.6 alkyl or C.sub.5 -C.sub.7 cycloalkyl or combined to form conjointly C.sub.4 -C.sub.9 alkylene; and
- (b) a thiolcarbamate herbicide soil life-extending nonphytotoxic amount of a compound having the formula ##STR18## wherein Y is oxygen or sulfur;
- Z is oxygen or sulfur;
- p is the integer 0, 1 or 2;
- R.sup.4 is C.sub.2 -C.sub.8 alkenyl; C.sub.2 -C.sub.8 alkenyl substituted with one or more halo groups; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 alkyl substituted with dioxolanyl, cyano or one or more hydroxy or C.sub.1 -C.sub.4 alkoxy groups; C.sub.1 -C.sub.3 alkyl substituted with one, two or three halo groups; C.sub.1 -C.sub.6 alkylthioalkyl; benzyl; benzyl substituted with one or more halo or trifluoromethyl groups; C.sub.3 -C.sub.6 alkynyl; C.sub.3 -C.sub.4 alkynyl substituted with phenyl; phenyl; or phenyl substituted with halo, one or more nitro, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl groups;
- R.sup.5 is C.sub.2 -C.sub.6 alkenyl substituted with phenyl or one or more halo groups; C.sub.2 -C.sub.6 alkenyl; C.sub.1 -C.sub.8 alkyl; C.sub.1 -C.sub.8 alkyl substituted with one or more halo groups; or C.sub.3 -C.sub.6 alkynyl;
- R.sup.6 is hydrogen; C.sub.2 -C.sub.6 alkenyl substituted with phenyl or one or more halo or C.sub.1 -C.sub.4 alkoxy groups; C.sub.2 -C.sub.6 alkenyl; C.sub.1 -C.sub.8 alkyl; C.sub.1 -C.sub.8 alkyl substituted with C.sub.3 -C.sub.6 cycloalkyl or one or more halo groups; C.sub.3 -C.sub.6 alkynyl; furfuryl; or benzyl; with the provisos that:
- when Y is oxygen or both Y and Z are sulfur, then p is zero;
- when Y is sulfur, Z is oxygen, R.sup.4 is allyl, 2-methylallyl, 2-butenyl, 3-chloroallyl or n-butyl, and R.sup.5 is allyl, then R.sup.6 is other than propyl or butyl;
- when Y is sulfur, Z is oxygen, R.sup.4 is either C.sub.1 -C.sub.5 alkyl, substituted benzyl, C.sub.3 -C.sub.6 haloalkenyl, 2-chloroethyl, methylthioethyl, or propargyl, and R.sup.5 is C.sub.1 -C.sub.5 alkyl, then R.sup.6 is other than C.sub.1 -C.sub.6 alkyl;
- when Y is sulfur and Z is oxygen, R.sup.4 is allyl, 3-chloroallyl, ethyl, n-butyl, methoxymethyl or ethoxymethyl, then not both R.sup.5 and R.sup.6 are allyl; and
- when Y and Z are each oxygen, then R.sup.4 is other than phenyl substituted with one or more C.sub.1 -C.sub.4 alkyl or one or more C.sub.1 -C.sub.4 haloalkyl.
- 2. An herbicidal composition according to claim 1 wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl, allyl or haloallyl; R.sup.2 is C.sub.1 -C.sub.6 alkyl; R.sup.3 is C.sub.1 -C.sub.6 alkyl or C.sub.5 -C.sub.7 cycloalkyl.
- 3. An herbicidal composition according to claim 2 wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl; R.sup.2 is C.sub.1 -C.sub.6 alkyl; R.sup.3 is C.sub.1 -C.sub.6 alkyl or cyclohexyl.
- 4. An herbicidal composition according to claim 1 wherein
- R.sup.4 is C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.8 alkenyl substituted with one, two or three halo groups; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted with dioxolanyl, cyano, or with one or two C.sub.1 -C.sub.2 alkoxy groups; C.sub.1 -C.sub.3 alkyl substituted with one or two halo groups; C.sub.1 -C.sub.4 alkylthioalkyl; benzyl; benzyl substituted with halo; C.sub.3 -C.sub.4 alkynyl; C.sub.3 -C.sub.4 alkynyl substituted with phenyl; phenyl; or phenyl substituted with C.sub.1 -C.sub.2 alkyl, halo or one or more nitro groups;
- R.sup.5 is C.sub.3 -C.sub.8 alkenyl substituted with phenyl or one, two or three halo groups; C.sub.3 -C.sub.8 alkenyl; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 alkyl substituted with halo; or C.sub.3 -C.sub.4 alkynyl;
- R.sup.6 is hydrogen; C.sub.3 -C.sub.8 alkenyl substituted with phenyl, or one, two or three halo groups; C.sub.3 -C.sub.6 alkenyl; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.3 -C.sub.4 cycloalkyl, or halo; benzyl; C.sub.3 -C.sub.4 alkynyl; or furfuryl.
- 5. An herbicidal composition according to claim 1 wherein
- p is zero or 1;
- R.sup.4 is vinyl; allylic; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted with dioxolanyl or cyano; C.sub.1 -C.sub.2 alkyl substituted with halo; C.sub.2 -C.sub.4 alkylthioalkyl; benzyl; benzyl substituted with halo; C.sub.3 -C.sub.4 alkynyl; C.sub.3 -C.sub.4 alkynyl substituted with phenyl; phenyl; or phenyl substituted with halo or one or two nitro groups;
- R.sup.5 is allylic; C.sub.3 -C.sub.6 alkenyl substituted with phenyl; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted with halo; C.sub.1 -C.sub.4 alkyl substituted with halo; or C.sub.3 -C.sub.4 alkynyl;
- R.sup.6 is hydrogen; allylic; C.sub.3 -C.sub.6 alkenyl substituted with phenyl; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted with C.sub.1 -C.sub.2 alkoxy or C.sub.3 -C.sub.4 cycloalkyl; C.sub.3 -C.sub.4 alkynyl; furfuryl; or benzyl;
- wherein allylic in said preferred embodiment for R.sup.5 and R.sup.6 refers to the following structure: ##STR19## wherein R.sup.7 is hydrogen, halo or C.sub.1 -C.sub.3 alkyl; R.sup.8 is hydrogen, halo or C.sub.1 -C.sub.3 alkyl; and R.sup.9 is hydrogen, halo or C.sub.1 -C.sub.3 alkyl.
- 6. An herbicidal composition according to claim 1 wherein
- p is zero or 1;
- R.sup.4 is vinyl; 2-methylallyl; 2-butenyl; 3butenyl; allyl; 3-haloallyl; 2-haloallyl; trihalo-2-butenyl; trihalo-3-butenyl; ethyl; methyl; n-propyl; n-butyl; iso-butyl; iso-propyl; 2'-(1,3-dioxolanyl) ethyl; cyanomethyl; 3-cyanopropyl; 2-haloethyl; methylthiomethyl; ortho-halo benzyl; 2-butynyl; propargyl; phenyl; ortho-halophenyl;
- R.sup.5 is allyl; 2-haloallyl; 3-haloallyl, iso-butyl; 2-butenyl; or n-propyl;
- R.sup.6 is hydrogen, C.sub.1 -C.sub.2 alkyl substituted with halo, or C.sub.1 -C.sub.2 alkoxy; C.sub.3 -C.sub.4 cycloalkyl; 3-haloallyl; 2-haloallyl; iso-butyl; 2-butenyl; allyl; furfuryl; benzyl; or 2-methyallyl.
- 7. An herbicidal composition according to claim 1 wherein
- p is zero or 1;
- R.sup.4 is vinyl; 2-methylallyl; 2-butenyl; allyl; 3-chloroallyl; 3,4,4-trifluoro-3-butenyl; 3,4,4-trifluoro-2-butenyl; ethyl; methyl; cyanomethyl; 2'-(1,3-dioxolanyl) ethyl; 2-chloroethyl; methylthiomethyl; 2-butynyl; propargyl; phenyl; or 2-chlorophenyl;
- R.sup.5 is 3-chloroallyl; 3-bromoallyl; or 2-chloroallyl; and
- R.sup.6 is 3-chloroallyl; 3-bromoallyl; 2-methylallyl; benzyl; cyclopropylmethyl; 2-chloroallyl; furfuryl; or methoxyethyl.
- 8. An herbicidal composition according to claim 1 wherein
- p is zero;
- R.sup.4 is ethyl; methyl; vinyl; allyl; 2'-(1,3-dioxolanyl) ethyl; 2-chloroethyl; 2-butynyl; propargyl; or 2-chlorophenyl;
- R.sup.5 is 3-chloroallyl; and
- R.sup.6 is 3-chloroallyl; cyclopropylmethyl; 2-methylallyl; or benzyl.
- 9. An herbicidal composition according to claim 1 wherein the thiolcarbamate herbicide is S-ethyl N,N-di-n-propyl thiolcarbamate, S-ethyl-N-ethyl-N-cyclohexyl thiolcarbamate, S-ethyl-N,N-di-isobutyl thiolcarbamate, S-n-propyl N,N-di-n-propyl thiolcarbamate, or S-ethylhexahydro-1H-azepine1-carbothioate.
- 10. An herbicidal composition according to claim 9 wherein the extender is ethyl-N,N-bis-(3-chloroallyl) thiolcarbamate.
- 11. An herbicidal composition according to claim 9 wherein the extender is vinyl N,N-bis-(3-chloroallyl) thiolcarbamate.
- 12. An herbicidal composition according to claim 9 wherein the extender is allyl-N-(3-chloroallyl)-N-cyclopropylmethyl thiolcarbamate.
- 13. An herbicidal composition according to claim 9 wherein the extender is propargyl-N,N-bis-(3-chloroallyl) carbamate.
- 14. An herbicidal composition according to claim 9 wherein the extender is 2-butynyl-N,N-bis-(3-chloroallyl) carbamate.
- 15. An herbicidal composition according to claim 9 wherein the extender is 2-chloroethyl-N,N-bis-(3-chloroallyl) carbamate.
- 16. An herbicidal composition according to claim 9 wherein the extender is allyl-N,N-bis-(3-chloroallyl) thiolcarbamate.
- 17. An herbicidal composition according to claim 9 wherein the extender is allyl-N,N-bis-(3-chloroallyl) carbamate.
- 18. An herbicidal composition according to claim 9 wherein the extender is either 2-chlorophenyl-N,N-bis-(3-chloroallyl) thiolcarbamate; allyl-N,N-bis-(3-chloroallyl) dithiocarbamate; allyl-N,-(3-chloroallyl)-N-benzyl thiolcarbamate; 2'-(1,3-dioxolanyl)ethyl-N,N-bis-(3-chloroallyl) dithiocarbamate; allyl-N-3-chloroallyl-N-2-methylallyl carbamate; or methyl-N,N-bis-(3-chloroallyl) dithiocarbamate.
- 19. An herbicidal composition according to claim 1 wherein the weight ratio of said thiolcarbamate herbicide to said extender is from about 0.2:1 to about 30:1.
- 20. An herbicidal composition according to claim 1 further comprising a non-phytotoxic antidotally effective amount of a thiolcarbamate herbicide antidote.
- 21. An herbicidal composition according to claim 1 further comprising a non-phytotoxic antidotally effective amount of an amide of a dihaloalkanoic acid.
- 22. An herbicidal composition according to claim 1 further comprising a non-phytotoxic antidotally effective amount of an amide of dichloroacetic acid.
- 23. An herbicidal composition according to claim 1 further comprising a non-phytotoxic antidotally effective amount of a compound having the formula ##STR20## wherein R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14 and R.sup.15 are variously independently hydrogen, lower alkyl or phenyl, or R.sup.10 and R.sup.11 taken together form an alkylene group, preferably a butylene, pentylene or hexylene group optionally substituted by one or two methyl groups; ##STR21## in which R.sup.16 may be one of a number of alkyl, alkenyl or alkynyl moieties; R.sup.17, R.sup.18, R.sup.19 and R.sup.20 are independently hydrogen or methyl; and n is 0 or 1; ##STR22## in which R.sup.21 is cyano; ##STR23## in which R.sup.22 is alkyl, haloalkyl or trialkoxymethyl; R.sup.23 is variously hydrogen, agriculturally acceptable cations or various hydrocarbamyl or substituted hydrocarbamyl moieties; and R.sup.24 is chloro, bromo, iodo, lower alkoxy or substituted or unsubstituted phenoxy; or ##STR24## wherein R.sup.25 represents the group ##STR25## in which R.sup.28 represents a C.sub.1 -C.sub.3 haloalkyl containing from 1 to 3 halogen atoms or a phenyl group optionally substituted;
- R.sup.26 represents a hydrogen atom, a methyl or a phenyl;
- R.sup.27 represents a C.sub.1 -C.sub.8 alkyl group, a C.sub.5 -C.sub.6 cycloalkyl group, a cyclohexylmethyl group, a phenyl group optionally substituted, a benzyl group optionally substituted, an allyl or propargyl group; and
- n is zero or one.
- 24. An herbicidal composition according to claim 23 wherein the antidote is N-diallyl-N-[2-(1,3-dioxolanyl)]methyl dichloroacetamide.
- 25. An herbicidal composition according to claim 23 wherein the thiolcarbamate herbicide is S-ethyl-N,N-di-n-propyl thiolcarbamate and the extender is ethyl-N,N-bis-(3-chloroallyl) thiolcarbamate.
- 26. An herbicidal composition according to claim 23 wherein the antidote is 2,2,5-trimethyl-N-dichloroacetyl oxazolidine.
- 27. An herbicidal composition according to claim 23 wherein the weight ratio of herbicide to antidote is from about 0.1:1 to about 40:1.
- 28. A method of controlling undesirable vegetation comprising applying to the locus where control is desired both
- (a) an herbicidally effective amount of a thiolcarbamate having the formula ##STR26## wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl; phenyl; C.sub.7 -C.sub.9 phenylalkyl; C.sub.3 -C.sub.6 alkenyl; C.sub.3 -C.sub.6 haloalkenyl; or C.sub.7 -C.sub.9 phenylalkyl, mono- or poly-substituted on the phenyl ring with halogen;
- R.sup.2 and R.sup.3 are either selected independently from C.sub.1 -C.sub.6 alkyl or C.sub.5 -C.sub.7 cycloalkyl or combined to form conjointly C.sub.4 -C.sub.9 alkylene; and
- (b) a thiolcarbamate herbicide soil life-extending nonphytotoxic amount of a compound having the formula ##STR27## wherein Y is oxygen or sulfur;
- Z is oxygen or sulfur;
- p is the integer 0, 1 or 2;
- R.sup.4 is C.sub.2 -C.sub.8 alkenyl; C.sub.2 -C.sub.8 alkenyl substituted with one or more halo groups; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 alkyl substituted with dioxolanyl, cyano or one or more hydroxy or C.sub.1 -C.sub.4 alkoxy groups; C.sub.1 -C.sub.3 alkyl substituted with one, two or three halo groups; C.sub.1 -C.sub.6 alkylthioalkyl; benzyl; benzyl substituted with one or more halo or trifluoromethyl groups; C.sub.3 -C.sub.6 alkynyl; C.sub.3 -C.sub.4 alkynyl substituted with phenyl; phenyl; or phenyl substituted with halo, one or more nitro, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl groups;
- R.sup.5 is C.sub.2 -C.sub.6 alkenyl substituted with phenyl or one or more halo groups; C.sub.2 -C.sub.6 alkenyl; C.sub.1 -C.sub.8 alkyl substituted with one or more halo groups; or C.sub.3 -C.sub.6 alkynyl;
- R.sup.6 is hydrogen; C.sub.2 -C.sub.6 alkenyl substituted with phenyl or one or more halo or C.sub.1 -C.sub.4 alkoxy groups; C.sub.2 -C.sub.6 alkenyl; C.sub.1 -C.sub.8 alkyl substituted with C.sub.3 -C.sub.6 cycloalkyl or one or more halo groups; C.sub.3 -C.sub.6 alkynyl; furfuryl; or benzyl; with the provisos that:
- when Y is oxygen or both Y and Z are sulfur, then p is zero;
- when Y is sulfur, Z is oxygen, R.sup.4 is allyl, 2-methylallyl, 2-butenyl, 3-chloroallyl or n-butyl, and R.sup.5 is allyl, then R.sup.6 is other than propyl or butyl;
- when Y is sulfur, Z is oxygen, R.sup.4 is either C.sub.1 -C.sub.5 alkyl, substituted benzyl, C.sub.3 -C.sub.6 haloalkenyl, 2-chloroethyl, methylthioethyl, or propargyl, and R.sup.5 is C.sub.1 -C.sub.5 alkyl, then R.sup.6 is other than C.sub.1 -C.sub.6 alkyl;
- when Y is sulfur and Z is oxygen, R.sup.4 is allyl, 3-chloroallyl, ethyl, n-butyl, methoxymethyl or ethoxymethyl, then not both R.sup.5 and R.sup.6 are allyl; and
- when Y and Z are each oxygen, then R.sup.4 is other than phenyl substituted with one or more C.sub.1 -C.sub.4 alkyl or one or more C.sub.1 -C.sub.4 haloalkyl.
- 29. A method according to claim 28 further comprising a nonphytotoxic antidotally effective amount of a thiolcarbamate herbicide antidote having the formula ##STR28## wherein R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14 and R.sup.15 are variously independently hydrogen, lower alkyl or phenyl, or R.sup.10 and R.sup.11 taken together form an alkylene group, preferably a butylene, pentylene or hexylene group optionally substituted by one or two methyl groups; ##STR29## in which R.sup.16 may be one of a number of alkyl, alkenyl or alkynyl moieties; R.sup.17, R.sup.18, R.sup.19 and R.sup.20 are independently hydrogen or methyl; and n is 0 or 1; ##STR30## in which R.sup.21 is cyano; ##STR31## in which R.sup.22 is alkyl, haloalkyl or trialkoxymethyl; R.sup.23 is variously hydrogen, agriculturally acceptable cations or various hydrocarbamyl or substituted hydrocarbamyl moieties; and R.sup.24 is chloro, bromo, iodo, lower alkoxy or substituted or unsubstituted phenoxy; or ##STR32## wherein R.sup.25 represents the group ##STR33## in which R.sup.28 represents a C.sub.1 -C.sub.3 haloalkyl containing from 1 to 3 halogen atoms or a phenyl group optionally substituted;
- R.sup.26 represents a hydrogen atom, a methyl or a phenyl;
- R.sup.27 represents a C.sub.1 -C.sub.8 alkyl group, a C.sub.5 -C.sub.6 cycloalkyl group, a cyclohexylmethyl group, a phenyl group optionally substituted, a benzyl group optionally substituted, an allyl or propargyl group; and
- n is zero or one.
- 30. A method of extending the soil life of a thiolcarbamate herbicide having the formula
- (a) an herbicidally effective amount of a thiolcarbamate having the formula ##STR34## wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl; phenyl; C.sub.7 -C.sub.9 phenylalkyl; C.sub.3 -C.sub.6 alkenyl; C.sub.3 -C.sub.6 haloalkenyl; or C.sub.7 -C.sub.9 phenylalkyl, mono- or poly-substituted on the phenyl ring with halogen;
- R.sup.2 and R.sup.3 are either selected independently from C.sub.1 -C.sub.6 alkyl or C.sub.5 -C.sub.7 cycloalkyl or combined to form conjointly C.sub.4 -C.sub.9 alkylene; and
- (b) a thiolcarbamate herbicide soil life-extending nonphytotoxic amount of a compound having the formula ##STR35## wherein Y is oxygen or sulfur;
- Z is oxygen or sulfur;
- p is the integer 0, 1 or 2;
- R.sup.4 is C.sub.2 -C.sub.8 alkenyl; C.sub.2 -C.sub.8 alkenyl substituted with one or more halo groups; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 alkyl substituted with dioxolanyl, cyano or one or more hydroxy or C.sub.1 -C.sub.4 alkoxy groups; C.sub.1 -C.sub.3 alkyl substituted with one, two or three halo groups; C.sub.1 -C.sub.6 alkylthioalkyl; benzyl; benzyl substituted with one or more halo or trifluoromethyl groups; C.sub.3 -C.sub.6 alkynyl; C.sub.3 -C.sub.4 alkynyl substituted with phenyl; phenyl; or phenyl substituted with halo, one or more nitro, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl groups;
- R.sup.5 is C.sub.2 -C.sub.6 alkenyl substituted with phenyl or one or more halo groups; C.sub.2 -C.sub.6 alkenyl; C.sub.1 -C.sub.8 alkyl; C.sub.1 -C.sub.8 alkyl substituted with one or more halo groups; or C.sub.3 -C.sub.6 alkynyl;
- R.sup.6 is hydrogen; C.sub.2 -C.sub.6 alkenyl substituted with phenyl or one or more halo or C.sub.1 -C.sub.4 alkoxy groups; C.sub.2 -C.sub.6 alkenyl; C.sub.1 -C.sub.8 alkyl; C.sub.1 -C.sub.8 alkyl substituted with C.sub.3 -C.sub.6 cycloalkyl or one or more halo groups; C.sub.3 -C.sub.6 alkynyl; furfuryl; or benzyl; with the provisos that:
- when Y is oxygen or both Y and Z are sulfur, then p is zero;
- when Y is sulfur, Z is oxygen, R.sup.4 is allyl, 2methylallyl, 2-butenyl, 3-chloroallyl or n-butyl, and R.sup.5 is allyl, then R.sup.6 is other than propyl or butyl;
- when Y is sulfur, Z is oxygen, R.sup.4 is either C.sub.1 -C.sub.5 alkyl, substituted benzyl, C.sub.3 -C.sub.6 haloalkenyl, 2-chloroethyl, methylthioethyl, or propargyl, and R.sup.5 is C.sub.1 -C.sub.5 alkyl, then R.sup.6 is other than C.sub.1 -C.sub.6 alkyl;
- when Y is sulfur and Z is oxygen, R.sup.4 is allyl, 3-chloroallyl, ethyl, n-butyl, methoxymethyl or ethoxymethyl, then not both R.sup.5 and R.sup.6 are allyl; and
- when Y and Z are each oxygen, then R.sup.4 is other than phenyl substituted with one or more C.sub.1 -C.sub.4 alkyl or one or more C.sub.1 -C.sub.4 haloalkyl.
- 31. A method according to claim 30 further comprising a non-phytotoxic antidotally effective amount of a compound having the formula ##STR36## wherein R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14 and R.sup.15 are variously independently hydrogen, lower alkyl or phenyl, or R.sup.10 and R.sup.11 taken together form an alkylene group, preferably a butylene, pentylene or hexylene group optionally substituted by one or two methyl groups; ##STR37## in which R.sup.16 may be one of a number of alkyl, alkenyl or alkynyl moieties; R.sup.17, R.sup.18, R.sup.19 and R.sup.20 are independently hydrogen or methyl; and n is 0 or 1; ##STR38## in which R.sup.21 is cyano; ##STR39## in which R.sup.22 is alkyl, haloalkyl or trialkoxymethyl; R.sup.23 is variously hydrogen, agriculturally acceptable cations or various hydrocarbamyl or substituted hydrocarbamyl moieties; and R.sup.24 is chloro, bromo, iodo, lower alkoxy or substituted or unsubstituted phenoxy; or ##STR40## wherein R.sup.25 represents the group ##STR41## in which R.sup.28 represents a C.sub.1 -C.sub.3 haloalkyl containing from 1 to 3 halogen atoms or a phenyl group optionally substituted;
- R.sup.26 represents a hydrogen atom, a methyl or a phenyl;
- R.sup.27 represents a C.sub.1 -C.sub.8 alkyl group, a C.sub.5 -C.sub.6 cycloalkyl group, a cyclohexylmethyl group, a phenyl group optionally substituted, a benzyl group optionally substituted, an allyl or propargyl group; and
- n is zero or one.
- 32. A method of minimizing the soil degradation of thiolcarbamate herbicides having the formula ##STR42## wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl; phenyl; C.sub.7 -C.sub.9 phenylalkyl; C.sub.3 -C.sub.6 alkenyl; C.sub.3 -C.sub.6 haloalkenyl; or C.sub.7 -C.sub.9 phenylalkyl, mono- or poly-substituted on the phenyl ring with halogen;
- R.sup.2 and R.sup.3 are either selected independently from C.sub.1 -C.sub.6 alkyl or C.sub.5 -C.sub.7 cycloalkyl or combined to form conjointly C.sub.4 -C.sub.9 alkylene;
- by applying to the soil a thiolcarbamate herbicide soil life-extending nonphytotoxic amount of a compound having the formula ##STR43## wherein Y is oxygen or sulfur;
- Z is oxygen or sulfur;
- p is the integer 0, 1 or 2;
- R.sup.4 is C.sub.2 -C.sub.8 alkenyl; C.sub.2 -C.sub.8 alkenyl substituted with one or more halo groups; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 alkyl substituted with dioxolanyl, cyano or one or more hydroxy or C.sub.1 -C.sub.4 alkoxy groups; C.sub.1 -C.sub.3 alkyl substituted with one, two or three halo groups; C.sub.1 -C.sub.6 alkylthioalkyl; benzyl; benzyl substituted with one or more halo or trifluoromethyl groups; C.sub.3 -C.sub.6 alkynyl; C.sub.3 -C.sub.4 alkynyl substituted with phenyl; phenyl; or phenyl substituted with halo, one or more nitro, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl groups;
- R.sup.5 is C.sub.2 -C.sub.6 alkenyl substituted with phenyl or one or more halo groups; C.sub.2 -C.sub.6 alkenyl; C.sub.1 -C.sub.8 alkyl; C.sub.1 -C.sub.8 alkyl substituted with one or more halo groups; or C.sub.3 -C.sub.6 alkynyl;
- R.sup.6 is hydrogen; C.sub.2 -C.sub.6 alkenyl substituted with phenyl or one or more halo or C.sub.1 -C.sub.4 alkoxy groups; C.sub.2 -C.sub.6 alkenyl; C.sub.1 -C.sub.8 alkyl; C.sub.1 -C.sub.8 alkyl substituted with C.sub.3 -C.sub.6 cycloalkyl or one or more halo groups; C.sub.3 -C.sub.6 alkynyl; furfuryl; or benzyl; with the provisos that:
- when Y is oxygen or both Y and Z are sulfur, then p is zero;
- when Y is sulfur, Z is oxygen, R.sup.4 is allyl, 2-methylallyl, 2-butenyl, 3-chloroallyl or n-butyl, and R.sup.5 is allyl, then R.sup.6 is other than propyl or butyl;
- when Y is sulfur, Z is oxygen, R.sup.4 is either C.sub.1 -C.sub.5 alkyl, substituted benzyl, C.sub.3 -C.sub.6 haloalkenyl, 2-chloroethyl, methylthioethyl, or propargyl, and R.sup.5 is C.sub.1 -C.sub.5 alkyl, then R.sup.6 is other than C.sub.1 -C.sub.6 alkyl;
- when Y is sulfur and Z is oxygen, R.sup.4 is allyl, 3-chloroallyl, ethyl, n-butyl, methoxymethyl or ethoxymethyl, then not both R.sup.5 and R.sup.6 are allyl; and
- when Y and Z are each oxygen, then R.sup.4 is other than phenyl substituted with one or more C.sub.1 -C.sub.4 alkyl or one or more C.sub.1 -C.sub.4 haloalkyl.
- 33. A method according to claim 32 further comprising a thiolcarbamate herbicide antidote for example having the formula ##STR44## wherein R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14 and R.sup.15 are variously independently hydrogen, lower alkyl or phenyl, or R.sup.10 and R.sup.11 taken together form an alkylene group, preferably a butylene, pentylene or hexylene group optionally substituted by one or two methyl groups; ##STR45## in which R.sup.16 may be one of a number of alkyl, alkenyl or alkynyl moieties; R.sup.17, R.sup.18, R.sup.19 and R.sup.20 are independently hydrogen or methyl; and n is 0 or 1; ##STR46## in which R.sup.21 is cyano; ##STR47## in which R.sup.22 is alkyl, haloalkyl or trialkoxymethyl; R.sup.23 is variously hydrogen, agriculturally acceptable cations or various hydrocarbamyl or substituted hydrocarbamyl moieties; and R.sup.24 is chloro, bromo, iodo, lower alkoxy or substituted or unsubstituted phenoxy; or ##STR48## wherein R.sup.25 represents the group ##STR49## in which R.sup.28 represents a C.sub.1 -C.sub.3 haloalkyl containing from 1 to 3 halogen atoms or a phenyl group optionally substituted;
- R.sup.26 represents a hydrogen atom, a methyl or a phenyl;
- R.sup.27 represents a C.sub.1 -C.sub.8 alkyl group, a C.sub.5 -C.sub.6 cycloalkyl group, a cyclohexylmethyl group, a phenyl group optionally substituted, a benzyl group optionally substituted, an allyl or propargyl group; and
- n is zero or one.
CROSS REFERENCE TO RELATED APPLICATIONS
This is a continuation of application Ser. No. 07/405,094 filed Sep. 8, 1989, now abandoned which is a file wrapper continuation of application Ser. No. 07/767,141, filed Aug. 21, 1985, now abandoned, which is a continuation-in-part of application Ser. No. 07/652,710, filed Sep. 19, 1984, now abandoned.
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Number |
Name |
Date |
Kind |
2913327 |
Tilles et al. |
Nov 1959 |
|
4299616 |
Hyzak |
Nov 1981 |
|
4629499 |
Felix et al. |
Dec 1986 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
862548 |
Jul 1957 |
GBX |
Continuations (2)
|
Number |
Date |
Country |
Parent |
405094 |
Sep 1989 |
|
Parent |
767141 |
Aug 1985 |
|
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
652710 |
Sep 1984 |
|