Claims
- 1. A herbicidal compound of the formula ##STR22## where X is F, Cl or Br; Y is Cl, Br, CHF.sub.2 O or CF.sub.3 ; Z is O, S, S(O), S(O).sub.2 or NR.sup.2 ; R is alkyl, lower halo alkyl, aryl, aralkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxy- or haloalkoxycarbonylalkyl, alkyl- or haloalkyl- or arylaminocarbonyl carboxyalkyl, aryloxycarbonylalkyl, aralkyloxycarbonylalkyl, aminocarbonylalkyl, lower alkylaminocarbonylalkyl, arylaminocarbonylalkyl, alkylsulfonylaminocarbonylalkyl or arylsulfonylaminocarbonylalkyl; R', is H or lower alkyl; and R.sup.2 is hydrogen, lower alkyl, lower alkoxy or aralkyloxy; and wherein any aryl moiety is monocyclic and any alkyl moiety has 1 to 6 carbon atoms.
- 2. A compound as in claim 1 in which Z is O.
- 3. A compound as in claim 1 in which Z is S, S(O) or S(O).sub.2.
- 4. A compound as in claim 1 in which Z is NR.sup.2.
- 5. A compound as in claim 2 in which R is ethyl.
- 6. A compound as in claim 5 in which X is F, Y is Cl, and R' is H.
- 7. A compound as in claim 3 in which X is F, Y is Cl or Br and R' is H.
- 8. A compound as in claim 4 in which X is F, Y is Cl or Br and R' is H.
- 9. A herbicidal composition containing an herbicidally effective amount of a compound of claim 1 in admixture with a suitable carrier.
- 10. A herbicidal composition containing an herbicidally effective amount of a compound of claim 6 in admixture with a suitable carrier.
- 11. A method of controlling weeds which comprises applying to the locus where control is desired an herbicidally effective amount of the composition of claim 9.
- 12. A method of controlling weeds which comprises applying to the locus where control is desired an herbicidally effective amount of the composition of claim 10.
- 13. The method of claim 12 wherein the locus where control is desired is planted with soybeans, corn, rice or wheat.
- 14. The method of claim 12 wherein the locus where control is desired is planted with soybeans.
- 15. The method of claim 12 wherein said locus is planted with paddy rice.
Parent Case Info
This application is a continuation-in-part of application Ser. No. 914,555, filed Oct. 3, 1986, now abandoned, which is a continuation-in-part of application Ser. No. 818,647, filed Jan. 10, 1986, now abandoned.
The invention described in this application pertains to weed control in agriculture, horticulture, and other fields where there is a desire to control unwanted plant growth. More specifically, the present application describes certain herbicidal aryl tetrahydrophthalimides, compositions of them, methods of preparing them, and methods for preventing or destroying undesired plant growth by preemergence or postemergence application of the herbicidal compositions to the locus where control is desired. The present compounds may be used to effectively control a variety of both grassy and broadleaf plant species. The present invention is particularly useful in agriculture; a number of the compounds described herein show a selectivity favorable to certain crops (e.g. soybeans, corn, rice, including paddy rice, and wheat on preemergence or postemergence treatment) at application levels which inhibit the growth or destroy the growth of a variety of weeds.
A particularly effective aspect of this invention relates to the herbicidal compound of the formula: ##STR2## where X is F, Y is Cl, R' is H, Z is O, and R is C.sub.2 H.sub.5. X may also be Cl or Br; Y may also be Br or CHF.sub.2 O or CF.sub.3.
Instead of ethyl, R may also be another alkyl of 1 to 6 carbon atoms (e.g., methyl, propyl, isopropyl, butyl or t-butyl); lower haloalkyl (e.g., chloroethyl or fluoropropyl); aryl (e.g., phenyl, or methoxy-- or chloro-substituted phenyl); aralkyl (e.g., benzyl); alkylcarbonyl (such as lower alkyl carbonyl, e.g., CH.sub.3 CO-- or C.sub.2 H.sub.5 CO--); haloalkylcarbonyl (such as lower haloalkylcarbonyl, e.g. ClCH.sub.2 CO--, FCH.sub.2 CO-- or ClCH.sub.2 CH.sub.2 CO--); alkoxy-- (or haloalkoxy--)carbonylalkyl (e.g., in which the alkoxy and alkyl moieties are each of 1 to 6 carbon atoms, such as CH.sub.3 OC(O)CH.sub.2 -- or C.sub.2 H.sub.5 OC (O)CH(CH.sub.3)-- or ClCH.sub.2 OC(O)CH.sub.2 --); alkyl-- (or haloalkyl-- or aryl--)aminocarbonyl (e.g., CH.sub.3 NHCO--); carboxyalkyl (e.g., --CH.sub.2 C(O)OH); aryloxycarbonylalkyl, e.g. ##STR3## aralkyloxycarbonylalkyl, e.g., ##STR4## aminocarbonylalkyl (e.g., NH.sub.2 C(O)CH.sub.2 --); lower alkylaminocarbonylalkyl (e.g., C.sub.2 H.sub.5 NHC(O)CH.sub.2 --); arylaminocarbonylalkyl, e.g., ##STR5## alkylsulfonylaminocarbonylalkyl (e.g., CH.sub.3 SO.sub.2 NHC(O)CH.sub.2); or arylsulfonylaminocarbonylalkyl, e.g., ##STR6##
Instead of being O, Z may also be S or S(O) or S(O).sub.2, with R and R' being as described herein.
Z may also be NR.sup.2 with R.sup.2 being hydrogen, lower alkyl (e.g., of 1 to 6 carbon atoms such as methyl or butyl), lower alkoxy (such as methoxy), aralkyloxy (e.g., benzyloxy), or R.sup.2 taken with R may be a divalent radical such as alkylene (e.g., butylene), alkylenoxyalkylene (e.g., as in compound 32 of Table 1), carbonylalkylenoxy (e.g., as in compound 33). R and R' may be as described herein.
Instead of H, R' may also be lower alkyl (e.g., of 1 to 6 carbon atoms such as methyl, ethyl, propyl or butyl).
In each aspect of the invention it is often preferable that any alkyl, alkenyl, alkynyl, or alkylene moiety (such as the hydrocarbon moiety of an alkoxy or haloalkoxy group) have less than 6 carbon atoms, e.g., 1 to 3 carbon atoms.
In a broader aspect of the invention, it relates to herbicidal compounds of the formula ##STR7## wherein Ar is a substituted phenyl radical having the group --CH(R')ZR in its 5-position (e.g. meta to the nitrogen of said formula), with the proviso that the compound is one whose Methoxy Analog or Propargyloxy Analog is a herbicide. The term "Methoxy Analog" is used here to designate a compound which is otherwise identical to said compound of Formula II except that it has a methoxy group instead of the --CH(R')ZR group of said compound of Formula II. The term "Propargyloxy Analog" is similarly used here for a compound which is otherwise identical to said compound of Formula II except that it has a propargyloxy group instead of the --CH(R')ZR group of said compound of Formula II. Preferably, "Ar" carries a substituent (i.e. other than H) at the 2-position or the 4-position of the phenyl radical, most preferably at both the 2- and 4-positions. Also, preferably R' is H and R is ethyl.
Herbicidal aryl tetrahydrophthalimides are disclosed in U.S. Pat. Nos. 4,292,070 (which describes compounds having a 5-propargyloxy substituent on the phenyl group) and 4,431,822.
The compounds of this invention preferably have Methoxy Analogs and Propargyloxy Analogs of marked herbicidal properties. For instance, said Analogs of the preferred compounds show at least 50% kill of at least one of the following species of plants when applied under at least one of the following modes at the rate of 0.5 kg/ha, and more preferably show such kill of at least 50% when applied at the rate of 0.1 kg/ha: Species; velvetleaf (Abutilon theophrasti), green foxtail (Setaria viridis); Modes: pre-emergent, postemergent. Testing for such herbicidal activity may be carried out in the manner described below (under the heading "Herbicidal Activity").
Representative compounds of this invention are listed in Table 1 below.
The compounds of this invention may be prepared by the use of steps generally described in the literature or by methods analogous or similar thereto and within the skill of the art.
In Examples 1, 8, 9 and 10 below the starting material is a substituted benzyl bromide, e.g., of the formula ##STR8## which is reacted with a nucleophile (e.g., an etherifying agent), to form, for instance, an intermediate ##STR9## then nitrated to place an NO.sub.2 group on the benzene ring, to form, for instance, an intermediate ##STR10## and then reduced to convert the NO.sub.2 group to an amino group to form, for instance, an intermediate ##STR11## and then reacted with tetrahydrophthalic anhydride to form the imide. The nitration may precede the reaction with the nucleophile; thus in Example 7 one may start with a substituted nitrotoluene, e.g., of the formula ##STR12## and convert the nitro group to a (protected) amino group, e.g., forming an intermediate ##STR13## then convert to the benzyl halide, such as a benzyl bromide, e.g., forming ##STR14## and then react with the nucleophile.
Example 2, in which R' is alkyl, illustrates a process in which there is formed a substituted benzaldehyde, e.g., of the formula ##STR15## which is converted in known manner e.g., in a series of reactions involving a Grignard reagent) to the corresponding secondary alcohol, e.g., ##STR16## Nitration of the alcohol (under mild conditions, such as with HNO.sub.3 in a solvent at a temperature of about -20.degree. to 5.degree. C.) before the reaction with the nucleophile not only places an NO.sub.2 group on the aromatic ring but also converts the alcoholic OH group to an --ONO.sub.2 group, forming, ##STR17## That --ONO.sub.2 group may than be converted to, e.g., an OR group by reaction with a nucleophile such as a conventional etherifying agent, e.g., an alkali metal alkoxide.
Examples 3 to 6 illustrate a process in which the substituted benzaldehyde, e.g., of the formula ##STR18## is nitrated and reduced to form the corresponding nitro alcohol, ##STR19## and the amino alcohol, e.g., ##STR20## and in which the alcoholic hydroxyl is reacted, to form the desired final compound, after the imide-forming reaction with the tetrahydrophthalic anhydride.
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Foreign Referenced Citations (6)
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Date |
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May 1982 |
EPX |
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Continuation in Parts (2)
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Number |
Date |
Country |
| Parent |
914555 |
Oct 1986 |
|
| Parent |
818647 |
Jan 1986 |
|
Patent Grant
4846882
