Chemistry: fertilizers – Processes and products – Forms or conditioning
Patent
1990-11-02
1992-11-03
Ford, John M.
Chemistry: fertilizers
Processes and products
Forms or conditioning
544332, 544323, 544321, C07D23969, A01N 4354
Patent
active
051603632
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
Herbicidal sulfonylureas are well known in the art. Exemplary of the patent literature teaching substituted phenyl sulfonylureas are the following: U.S. Pat. Nos. 4,383,113; 4,394,506; 4,478,635; 4,515,626; 4,659,369; 4,678,498; 4,705,556; and 4,710,221; EP-A-235,449; and South African Patent Applications 84/2722 and 84/5216.
SUMMARY OF THE INVENTION
This application pertains to novel compounds of Formula I, agriculturally suitable compositions containing them and their method-of-use as preemergent and/or postemergent herbicides or plant growth regulants. ##STR1## wherein R is H or CH.sub.3 ; ##STR2## R.sub.2 is ##STR3## or CHO; R.sub.3 is H, OCH.sub.3, CH.sub.3 or Cl; -C.sub.3 haloalkyl, allyl or propargyl; -C.sub.4 cycloalkyl or cyclopropylmethyl; -C.sub.4 cycloalkyl, cyclopropylmethyl, C.sub.1 -C.sub.2 alkoxy, CN or Cl; NHC(O)CH.sub.3 or W.sub.2 R.sub.16 ; -C.sub.3 haloalkyl; C.sub.2 -C.sub.3 haloalkyl; C.sub.4 -C.sub.5 cycloalkylalkyl; ; and NHCH.sub.3, or N(CH.sub.3).sub.2 ; ##STR4## 3) when R.sub.2 is ##STR5## then R.sub.1 is CO.sub.2 R.sub.4 ; 4) When R.sub.16 is H, W.sub.2 is O.
In the above definitions, the term "alkyl, " used either alone or in compound words such as "alkoxyalkyl" or "haloalkyl, " includes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl or isopropyl.
Alkoxy includes methoxy, ethoxy, n-propyloxy and isopropyloxy.
Alkoxyalkyl includes methoxymethyl through the different methoxypropyl and propyloxymethyl isomers.
Cycloalkyl includes cyclopropyl and cyclobutyl.
C.sub.4 -C.sub.5 cycloalkylalkyl means cyclopropylmethyl through cyclopropylethyl or cyclobutylmethyl.
The term "halogen," either alone or in compound words such as "haloalkyl," means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl," said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH.sub.2 CH.sub.2 F, CF.sub.2 CF.sub.3 and CH.sub.2 CHFCl.
The total number of carbon atoms in a substituent group is indicated by the C.sub.i -C.sub.j prefix where i and j are numbers from 1 to 5. For example, C.sub.1 -C.sub.3 alkyl would designate methyl through the propyl isomers; C.sub.2 alkoxyalkyl would designate CH.sub.2 OCH.sub.3 ; C.sub.4 alkoxyalkyl would designate the various isomers of an alkyl group substituted with a alkoxy group contianing a total of 4 carbon atoms, examples including but not limited to CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3, CH.sub.2 OCH(CH.sub.3).sub.2, CH(CH.sub.3)OCH.sub.2 CH.sub.3, CH(CH.sub.2 CH.sub.3)OCH.sub.3, CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 and CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3.
Preferred compounds for reasons of increased ease of synthesis and/or greater herbicidal efficacy are: CH.sub.2 OCH.sub.3 ; CH.sub.2 OCH.sub.3 ; and ##STR6## 4) Compounds of Preferred 3 where R.sub.13 is W.sub.2 R.sub.16. ##STR7## 7) Compounds of Preferred 2 where R.sub.2 is CHO.
Specifically preferred for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy and/or greatest safety to sugar beets are: 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]amino]sulfonyl]-5-(metho xymethyl)benzoate, m.p. 182.degree.-184.degree. C.; and 6-dimethoxypyrimidin-2-yl)amino]carbonyl]amino]sulfonyl]-5-(hydroxymethyl) benzoate, m.p. 182.degree.-185.degree. C.
DETAILED DESCRIPTION OF THE INVENTION
Synthesis
The preparation of compounds of Formula I can be accomplished using a wide variety of methods well known in the art. Some of the more general methods used to prepare these materials are described below in Equations 1 and 2.
Many of the compounds of Formula I can be prepared by the coupling reaction of sulfonyl isocyanates of Formula II with heterocyclic amines of Formula III as shown below in Equation 1. Equation 1 ##STR8## wherein, R, R.sub.1 R.sub.3, X, Y and Z are as previously defined; ##STR9## R.sub.13 is CN, SCN, W.sub.2 R.sub.16 ; and W.sub.2, R.sub.12, R.sub.13 and R.sub.16 are as previously defined.
A useful reference for this co
E. I. Du Pont de Nemours and Company
Ford John M.
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