This invention relates to ureas and isoureas having agricultural activity and in particular pre- and post-emergence herbicidal activity.
Netherlands Pat. No. 121,788 published Sept. 15, 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides: ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.2 is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl. PA1 m is the integer one or two; PA1 M is of alkali metal, alkaline earth metal or ammonium; PA1 R.sup.1 and R.sup.2 are each independently hydrogen, alkyl, alkoxy, alkynyl, phenyl, substituted phenyl having a maximum of three substituents said substituents being alkyl bromine, chlorine, alkoxy, phenoxy, mono and dihalogenated phenoxy said halogen being chlorine or bromine, or the group ##STR9## and R.sup.4 and R.sup.5 are each independently hydrogen or alkyl. PA1 R.sup.a is CH.sub.3 or CH.sub.3 CH.sub.2 ; PA1 R=H; C.sub.1 -C.sub.12 alkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.1 -C.sub.4 alkyl substituted with one to four substituents selected from 0-3 F, 0-3 Cl, 0-3 Br, 0-2 OCH.sub.3, 0-1 cyano, 0-1 CO.sub.2 R.sub.1 ' where R.sub.1 ' is C.sub.1 -C.sub.3 alkyl; CO.sub.2 R.sub.1 '; C.sub.2 -C.sub.4 alkenyl substituted with 1-3 Cl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.5 -C.sub.6 cycloalkenyl; C.sub.5 -C.sub.6 cycloalkyl substituted with substituents selected from 1-3 CH.sub.3 or one of CH.sub.3 CH.sub.2, Cl, OCH.sub.3 ; C.sub.4 -C.sub.7 cycloalkylalkyl; ##STR14## or a single bond; where PA1 R.sub.2 ' is H or CH.sub.3, n is 0 or 1; PA1 R.sub.1.sup.I and R.sub.1.sup.II are independently H, CH.sub.3, Cl or OCH.sub.3 ; PA1 T=O or ##STR15## where R.sub.I.sup.III is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; PA1 R.sub.2 =H, F, Cl, Br, C.sub.1 -C.sub.3 alkyl, NO.sub.2, SO.sub.2 CH.sub.3, OCH.sub.3, SCH.sub.3, CF.sub.3 or N(CH.sub.3).sub.2 ; PA1 R.sub.3 =H, F, Cl, Br or CH.sub.3 ; ##STR16## where R.sub.4 =H or CH.sub.3 ; PA1 R.sub.5 =H, CH.sub.3 or OCH.sub.3 ; PA1 W=O or S; ##STR17## where Z=CH, N, C--F, C--Cl, C--Br, C--CH.sub.3, C--OCH.sub.3, C--CH.sub.2 CH.sub.3 or C--CH.sub.2 CH.sub.2 Cl; PA1 X=H, Cl, --CH.sub.3, --OCH.sub.3, --OCH.sub.2 CH.sub.3 or --OCH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 Y=H; Cl; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted with --OCH.sub.3, --OC.sub.2 H.sub.5, --CN, --CO.sub.2 CH.sub.3, --CO.sub.2 C.sub.2 H.sub.5 or 1-3 atoms of F, Cl, Br; C.sub.3 -C.sub.4 alkenyl; --CH.sub.2 C.tbd.CR.sub.6 where R.sub.6 is H, --CH.sub.3, --CH.sub.2 Cl; --A--(CH.sub.2).sub.n' --A.sub.1 --(C.sub.1 -C.sub.3 alkyl) where n' is 2 or 3, A is O or S and A.sub.1 is O, S or SO.sub.2 ; ##STR18## --NH(C.sub.1 -C.sub.4 alkyl), --N(C.sub.1 -C.sub.4 alkyl).sub.2, C.sub.1 -C.sub.6 alkoxy; SCN; --N.sub.3 ; NR.sub.7 R.sub.8 where R.sub.7 is H or CH.sub.3 and R.sub.8 is H, --OCH.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkyl substituted with --CN or --CO.sub.2 CH.sub.3 or CO.sub.2 C.sub.2 H.sub.5, C.sub.3 -C.sub.4 alkenyl, or C.sub.2 -C.sub.3 alkyl substituted with OCH.sub.3 or OC.sub.2 H.sub.5, or R.sub.7 and R.sub.8 can be taken together to form --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; --O--R.sub.9 where R.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br, C.sub.1 -C.sub.4 alkyl substituted with cyano, C.sub.3 -C.sub.4 alkenyl, --CH.sub.2 C.tbd.CR.sub.6, where R.sub.6 is as previously defined, ##STR19## --SR.sub.10 where R.sub.10 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.2 alkyl substituted with CN, allyl or propargyl; PA1 X.sub.1 =H, Cl, OCH.sub.3, OCH.sub.2 CH.sub.3 or CH.sub.3 ; PA1 Y.sub.1 =H, OCH.sub.3 or CH.sub.3 ; PA1 X.sub.II =O or CH.sub.2 ; PA1 X.sub.1.sup.I and Y.sub.1.sup.I =CH.sub.3 or OCH.sub.3 ; PA1 W'=SR.sub.11 or OR.sub.12 ; where R.sub.11 and R.sub.12 =C.sub.1 -C.sub.12 alkyl; C.sub.3 -C.sub.4 alkenyl; CH.sub.2 CH.sub.2 OCH.sub.3 ; CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 ; CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 ; benzyl; ##STR20## where R.sub.13 is H or CH.sub.3, PA1 R.sub.14 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.11 also= ##STR21## CN, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, phenyl and phenyl substituted with CH.sub.3 or Cl; ##STR22## where Z.sup.I =CH or N; PA1 Y.sub.1.sup.I =CH.sub.3 or OCH.sub.3 ; PA1 X.sub.2 =CH.sub.3 ; C.sub.1 -C.sub.4 alkoxy; O(CH.sub.2).sub.n" OR.sub.15 where n" is 1-3, R.sub.15 is C.sub.1 -C.sub.3 alkyl; OCHR.sub.16 CO.sub.2 R.sub.17 where R.sub.16 is H or CH.sub.3 ; OCH.sub.2 CF.sub.3 or OCH.sub.2 CCl.sub.3 ; R.sub.17 is C.sub.1 -C.sub.3 alkyl; and PA1 X.sub.II =O or CH.sub.2 ; PA1 (1) when Y contains .gtoreq.4 carbon atoms, R contains .ltoreq.4 carbon atoms; PA1 (2) when X is Cl, then Y is Cl; PA1 (3) when X and Y are both H, then R is .ltoreq.4 carbon atoms; PA1 (4) when Z.noteq.N or CH, then X=H, CH.sub.3, OCH.sub.3 or Cl and Y=H, CH.sub.3 or OCH.sub.3 ; PA1 (5) both X.sub.1 and Y.sub.1 cannot be H; and PA1 (6) when R.sub.1.sup.IV is ##STR23## then R.sub.4 and R.sub.5 are hydrogen and R.ltoreq.5 carbon atoms; (7) when T is .dbd.N--OR.sub.1.sup.III, then R contains .ltoreq.5 carbon atoms; PA1 (1) A compound of the generic scope where R.sub.4 and R.sub.5 are H and W is oxygen; PA1 (2) A compound of Preferred 1 where R.sub.2 is H, F, Cl, Br, C.sub.1 -C.sub.3 alkyl, OCH.sub.3 and R.sub.3 is H in the position para to the sulfonyl group; PA1 (3) A compound of Preferred 2 where R.sub.1 is ##STR24## (4) A compound of Preferred 3 where R is H, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 cycloalkyl, or ##STR25## where R.sub.1.sup.I and R.sub.1.sup.II are independently H, CH.sub.3, Cl or OCH.sub.3 ; PA1 (5) A compound of Preferred 4 where X is CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 and Y is H, C.sub.1 -C.sub.3 alkyl, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, --OCH.sub.2 CO.sub.2 --(C.sub.1 -C.sub.2 alkyl), ##STR26## O--(C.sub.1 -C.sub.3 alkyl), O--(C.sub.3 -C.sub.4 alkenyl), NR.sub.7 R.sub.8 where R.sub.7 is H or CH.sub.3 or R.sub.8 is C.sub.1 -C.sub.3 alkyl, and Z=CH or N; PA1 (6) A compound of Preferred 5 where ##STR27## (7) A compound of Preferred 6 where T=O; and (8) A compound of Preferred 7 where R.sub.1 is ##STR28## (9) A compound of Preferred 8 where R is H or C.sub.1 -C.sub.4 alkyl. PA1 R.sub.1.sup.IV is ##STR38## X is H, Cl, Br, CH.sub.3, CH.sub.3 CH.sub.2, C.sub.1 -C.sub.3 alkoxy, CF.sub.3, CH.sub.3 S or CH.sub.3 OCH.sub.2 ; PA1 Y is CH.sub.3 or CH.sub.3 O; PA1 Z is N, CH, C--Cl, C--Br, C--CH.sub.3, --C--CH.sub.2 CH.sub.3 or --C--CH.sub.2 CH.sub.2 Cl; PA1 Y' is H, CH.sub.3, OCH.sub.3 or Cl; PA1 Q is O or CH.sub.2 ;
U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2## wherein R.sub.1 is hydrogen or lower saturated aliphatic acyl and
The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides as being useful as antidiabetic agents: ##STR3## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al. Chem Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR4## wherein R is butyl, phenyl, or ##STR5## and R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR6## Based upon similarity to a known compound, the author speculated that the foregoing compound might have a hypoglycemic activity.
U.S. Pat. No. 3,823,007 discloses isourea salts as herbicides: ##STR7## wherein R.sub.n is chloro, bromo, iodo, cyano, alkyl alkoxy, nitro, amino or ##STR8## R.sup.3 is hydrogen or alkyl; n is the integer one to three;
U.S. Pat. No. 3,714,209 discloses the isopropylidineaminoethanol salt of p-nitrobenzenesulfonylisourea as a herbicide: ##STR10##
Substituted-pyrimidinyl sulfonylureas of the following formula, which are also para-substituted on the phenyl ring, are disclosed in Farmco Ed. Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959)]: ##STR11## wherein R=H or CH.sub.3.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists however, for more effective herbicides.
USPTO Backgrounds
USPTO Backgrounds