Herbicidal sulfonamides

BACKGROUND OF THE INVENTION
This invention relates to a novel class of sulfonamides and their use as herbicides and plant growth regulants.
U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula: ##STR1## wherein
R.sub.1 is ##STR2##
R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl;
R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;
R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom;
R.sub.8 is hydrogen, methyl, chlorine or bromine;
R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine;
W and Q are independently oxygen or sulfur;
n is 0, 1 or 2;
X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and
Y is methyl or methoxy; or their agriculturally suitable salts; provided that:
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen;
(b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and
(c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen.
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: ##STR3## 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.
U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR4## wherein
R.sub.1 is hydrogen or lower saturated aliphatic acyl; and
R.sub.2 is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl.
The disclosed compounds are said to provide control of crabgrass, cress, endive, closer and Poa annua.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR5## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al., Chem. Ab., 53, 18052g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR6## wherein R is butyl, phenyl or ##STR7## 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: ##STR8## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
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)]: ##STR9## wherein R=H or CH.sub.3.
Unexamined European Pat. No. 7687 discloses, among others, herbicidal sulfonylures of the general structure: ##STR10## where
R is H, alkyl, alkenyl, aryl, etc.;
R.sub.6 is H or alkyl; or
R and R.sub.6 can be taken together to form --(CH.sub.2).sub.4, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.6 --, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 --.
U.S. Ser. No. 209,307, filed Nov. 24, 1980, discloses, among others, herbicidal sulfonylureas of the general structure: ##STR11## where
R is as disclosed in U.S. Ser. No. 029,281, now abandoned; and
R.sub.6 is ##STR12##
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 shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of 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.
SUMMARY OF THE INVENTION
This invention relates to compounds of Formula I and their agriculturally suitable salts, suitable agricultural compositions containing them and their method of use as general and/or selective pre-emergence and/or post-emergence herbicides and as plant growth regulants: ##STR13## wherein
A is a five- or six-membered aromatic heterocycle, a five- or six-membered dihydroaromatic heterocycle or a six-membered tetrahydroaromatic heterocycle which contains 1-4 heteroatoms selected from 0-1 oxygen atoms, 0-1 sulfur atoms, and/or 0-4 nitrogen atoms; the heterocycles may be optionally substituted with 1-4 CH.sub.3, 1-2 OCH.sub.3, 0-1 SCH.sub.3, 0-1 Cl, 0-1 N(CH.sub.3).sub.2, or 0-1 CN groups;
R is H or CH.sub.3 ;
R.sub.1 is H, F, Cl, Br, CH.sub.3, OCH.sub.3, CF.sub.3 or NO.sub.2 ;
R.sub.2 is H or CH.sub.3 ;
R.sub.3 is H or CH.sub.3 ;
R.sub.4 is ##STR14##
X is CH.sub.3, OCH.sub.3 or Cl;
Y is H, CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ;
Y.sub.1 is H, Cl, CH.sub.3 or OCH.sub.3 ; and
Z is CH, CCH.sub.3 or N
provided that
(1) the bond between N--R and A is attached to a nitrogen or carbon atom of A;
(2) when A is a thiophene or furan ring, the bond between NR and A is not at the 2- or 5-position of the heterocycle; and
(3) when X is Cl, then Z is CH and Y is CH.sub.3, OCH.sub.3, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2.
Preferred for higher herbicidal activity and/or more favorable ease of synthesis are:
(1) Compounds of Formula I wherein A is an unsubstituted or substituted six-membered aromatic heterocycle containing one to three nitrogen atoms;
(2) Compounds of Formula I wherein A is an unsubstituted or substituted six-membered dihydroaromatic heterocycle containing two nitrogen atoms;
(3) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one to four nitrogen atoms;
(4) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one or two nitrogen atoms and one oxygen or one sulfur atom;
(5) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one oxygen or one sulfur atom;
(6) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered dihydroaromatic heterocycle containing one nitrogen atom and optionally one heteroatom selected from nitrogen, oxygen or sulfur;
(7) Compounds of Formula I wherein A is an unsubstituted or substituted six-membered tetrahydroaromatic heterocycle containing one nitrogen atom and optionally one heteroatom selected from nitrogen, oxygen or sulfur;
(8) Compounds of Preferred (1)-(7) wherein ##STR15##
Y is CH.sub.3 or OCH.sub.3 ; and
Z is CH or N;
(9) Compounds of Preferred (8) wherein A is unsubstituted or optionally substituted with 0-4 CH.sub.3 or 0-2 OCH.sub.3 groups;
(10) Compounds of Preferred (9) wherein A is a pyridine, a pyrimidine or a 1,3,5-triazine;
(11) Compounds of Preferred (9) wherein A is a pyrrole, an imidazole, a pyrazole, or a 1,2,4-triazole;
(12) Compounds of Preferred (9) wherein A is an isoxazole, an oxazole, a 1,3,4-oxadiazole, a thiazole, a 1,2,3-thiadiazole, or a 1,3,4-thiadiazole;
(13) Compounds of Preferred (9) wherein A is a 4,5-dihydroimidazole, a 4,5-dihydroisoxazole, a 4,5-dihydrooxazole, a 4,5-dihydropyrazole, or a 4,5-dihydrothiazole;
(14) Compounds of Preferred (9) wherein A is a tetrahydropyrimidine, a tetrahydro-1,2,-oxazine, a tetrahydrol,3-oxazine, or a tetrahydro-1,3-thiazine;
(15) Compounds of Preferred (10)-(14) wherein R, R.sub.1, R.sub.2 and R.sub.3 are H, and A is unsubstituted, or, optionally substituted with one methyl group.
Specifically Preferred for highest herbicidal activity and/or most favorable ease of synthesis are:
2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(4,6-dimethylpyrimidin-2-yl)benzamide, m.p. 198.degree.-199.degree.;
2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(2-pyridinyl)benzamide, m.p. 206.degree.-207.degree.;
2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminocarbonyl]-N-(1,2,4-triazol-3-yl)benzamide, m.p. 226.degree.-230.degree.;
2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1-methyl-1H-pyrazol-3-yl)benzamide, m.p. 194.degree.-197.degree.;
2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(thiazol-2-yl)benzamide, m.p. 185.degree.-187.degree.;
2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1,3,4-thiadiazol-2-yl)benzamide, m.p. 172.degree.-173.degree.;
N-(3,4-dimethylisoxazol-5-yl)-2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzamide, m.p. 149.degree.-151.degree..
Synthesis
The compounds of Formula I can be prepared from the corresponding esters by reaction with the heterocyclic amine III in the presence of an equivalent amount of trimethylaluminum according to Equation 1. ##STR16##
According to the procedure of A. Basha, M. Lipton, and S. W. Weinreb, Tetrahedron Letters, 4171 (1977), the heterocyclic amine and the trimethylaluminum are mixed in methylene chloride, followed by the addition of a methyl ester of Formula II. The mixture is then heated at reflux for 12 to 24 hours.
The product can be isolated by addition of aqueous hydrochloric acid to decompose and dissolve the aluminum complexes and salts. Direct filtration of the precipitate or separation of the methylene chloride phase followed by evaporation yields the desired product which may be purified by crystallization or column chromatography.
The preparation of esters of Formula II is described in European Patent Application No. 7687.
Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by treating compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g. hydroxide, alkoxide, carbonate or hydride) quaternary amine salts can be made by similar techniques. Detailed examples of such techniques are given in U.S. Pat. No. 4,127,405, the disclosure of which is herein incorporated by reference.

The compounds of this invention and their preparaton are further illustrated by the following examples wherein temperatures are given in degrees centigrade and all parts are by weight unless otherwise indicated.
EXAMPLE 1
2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(4,6-dimethylpyrimidin-2-yl)benzamide
To 1.44 g of trimethylaluminum (10 ml of a 2M solution of trimethylaluminum in toluene) in 100 ml of methylene chloride was added 2.5 g of 2-amino-4,6-dimethylpyrimidine with stirring at ambient temperature. To this mixture was added 4.0 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide and the solution refluxed for 18 hours. The reaction mixture was then treated with aqueous hydrochloric acid and the precipitated product was found to be nearly pure by thin layer chromatography (TLC) on silica gel with an eluting solvent of ethyl acetate. Trituration of the solid with methylene chloride resulted in pure product (1.8 g); m.p. 198.degree.-199.degree. C.; IR: 3200 cm.sup.-1, NH, 1720 cm.sup.-1 sulfonylurea carbonyl, 1700 cm.sup.-1 amide carbonyl.
NMR: 2.2 ppm s, 6H, CH.sub.3 on pyrimidine, 3.9 ppm s, 6H, OCH.sub.3 on pyrimidine, 5.8 ppm, s, 1H proton in 5-position on the dimethoxypyrimidine, 6.7 ppm s, 1H, proton in 5-position of dimethylpyrimidine, 7.4-7.8 ppm and 8.0-8.4 ppm M, 4H, aromatic protons.
EXAMPLE 2
2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(2-pyridinyl)benzamide
To a slurry of 4.0 g of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide in 100 ml of methylene chloride was added by syringe 10 of a 2M solution of trimethylaluminum in toluene (1.44 g of Al(CH.sub.3).sub.3). Evolution of methane gas was seen and the solution became homogeneous. 2-Aminopyrimidine (1.9 g) was then added and the mixture was heated at reflux for 18 hours. The reaction mixture was then treated with aqueous hydrochloric acid and the precipitated product was purified by trituration in methylene chloride, 1.35 g, m.p. 206.degree.-207.degree. C., IR: 1710 cm.sup.-1 sulfonylurea carbonyl, 1680 cm.sup.-1 amide carbonyl.
NMR: in TFA, 2.8 ppm, CH.sub.3 on pyrimidine, 4.3 ppm, OCH.sub.3 on pyrimidine, 6.8 ppm, proton in 5-position of pyrimidine, 7.8-8.0 ppm and 8.4-8.6 ppm, aromatic protons.
EXAMPLE 3
2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1,2,4-triazol-3-yl)benzamide
To a slurry of 4.0 g of N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide in 100 ml of methylene chloride was added by syringe 10 ml of a 2M solution of trimethylaluminum in toluene (1.44 g of Al(CH.sub.3).sub.3). Evolution of methane gas was seen. 3-Amino-1,2,4-triazole (1.7 g) was then added and the mixture was heated at reflux for 18 hours. The reaction mixture was then treated with aqueous hydrochloric acid and the precipitated product was purified by trituration in methylene chloride, 0.63 g, m.p. 176.degree.-179.degree. C. NMR in TFA 2.9 ppm s, CH.sub.3 on triazine, 4.4 ppm s, OCH.sub.3 on triazine, 7.8-8.0 ppm and 8.2-8.5 ppm M, aromatic.
EXAMPLE 4
2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(thiazol-2-yl)benzamide
To a solution of 2-aminotriazole (2.1 g) in 100 ml of methylene chloride was added 10 ml of a 2M solution in toluene of trimethylaluminum (1.44 g of Al(CH.sub.3).sub.3) by syringe. Evolution of methane gas was seen and the solution became homogeneous. To this mixture was added 4.0 g of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide and the homogeneous solution was heated at reflux for 18 hours. The reaction mixture was then heated with aqueous hydrochloric acid and the precipitated product isolated by filtration, 1.42 g, m.p. 185.degree.-187.degree. C. IR: 1690 cm.sup.-1 and 1700 cm.sup.-1 unresolved double carbonyl, NMR: in TFA 2.7 ppm s, CH.sub.3 pyrimidine, 4.2 ppm s, OCH.sub.3 on pyrimidine, 6.7 ppm s, proton in 5-position on pyrimidine, 7.8-8.0 ppm and 8.4-8.5 ppm M, aromatic, 7.6, 7.7 ppm D, thiazole.
EXAMPLE 5
2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1,3,4-thiadiazol-2-yl)benzamide
To a solution of 2-amino-1,3,4-thiadiazole (2.1 g) in 100 ml of methylene chloride was added 10 ml of a 2M solution in toluene of trimethylaluminum (1.44 g of Al(CH.sub.3).sub.3) by syringe. Evolution of methane gas was seen from the homogeneous solution. To this mixture was added 4.0 g of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarboyl]-2-methoxycarbonylbenzenesulfonamide and the slurry was heated at reflux for 18 hours. The reaction mixture was then heated with aqueous hydrochloric acid and the precipitated product was purified by trituration in methylene chloride, 1.61 g, m.p. 172.degree.-173.degree. C. IR: 1700 cm.sup.-1 unresolved carbonyls, NMR: in TFA 2.9 ppm s, CH.sub.3 pyrimidine, 4.4ppm s, OCH.sub.3 on pyrimidine, 5.4 ppm s, thiadiazole, 6.9 ppm s, proton in 5-position on pyrimidine, 8.1 and 8.5 ppm M, aromatic.
Using the procedures and examples described above and choosing the appropriate compounds of Formulae II and III (as illustrated in Table I), the compounds described in Tables II-VII may be prepared.
TABLE I______________________________________A: Structures______________________________________ ##STR17## ##STR18## ##STR19## ##STR20## ##STR21## ##STR22## ##STR23## ##STR24## ##STR25## ##STR26## ##STR27## ##STR28## ##STR29## ##STR30## ##STR31## ##STR32## ##STR33## ##STR34## ##STR35## ##STR36## ##STR37## ##STR38## ##STR39## ##STR40## ##STR41## ##STR42## ##STR43## ##STR44## ##STR45## ##STR46## ##STR47## ##STR48## ##STR49## ##STR50## ##STR51## ##STR52## ##STR53## ##STR54## ##STR55## ##STR56## ##STR57## ##STR58## ##STR59## ##STR60## ##STR61## ##STR62## ##STR63## ##STR64## ##STR65## ##STR66## ##STR67## ##STR68## ##STR69## ##STR70## ##STR71## ##STR72## ##STR73## ##STR74## ##STR75## ##STR76## ##STR77## ##STR78## ##STR79## ##STR80## ##STR81## ##STR82## ##STR83## ##STR84## ##STR85## ##STR86## ##STR87## ##STR88## ##STR89## ##STR90##______________________________________
TABLE II__________________________________________________________________________ ##STR91##A R R.sub.1 R.sub.2 R.sub.3 R.sub.5 R.sub.6 X Y m.p.(.degree.C.)__________________________________________________________________________1 H H H H H H CH.sub.3 CH.sub.31 H H H H 4-CH.sub.3 H CH.sub.3 CH.sub.32 H H H H H H CH.sub.3 OCH.sub.32 H H H H 5-CH.sub.3 H CH.sub.3 CH.sub.33 H H H H 2-CH.sub.3 5-CH.sub.3 CH.sub.3 OCH.sub.33 H H H H H H CH.sub.3 OCH.sub.34 H H H H H H OCH.sub.3 OCH.sub.35 H H H H H H CH.sub.3 OCH.sub.35 H 5-Cl H H H H OCH.sub.3 OCH.sub.36 H H H H H H CH.sub.3 CH.sub.3 208-2116 H H H H H H CH.sub.3 OCH.sub.3 203-2067 H H H H 3-CH.sub.3 4-CH.sub.3 CH.sub.3 CH.sub.38 H 5-F H H H H OCH.sub.3 OCH.sub.38 H 5-Br H H 4-CH.sub.3 H CH.sub.3 OCH.sub.39 H H H H H H CH.sub.3 CH.sub.310 H H H H H H CH.sub.3 OCH.sub.311 H H H H H H OCH.sub.3 OCH.sub.312 H H H H 5-SCH.sub.3 -- CH.sub.3 CH.sub.312 H H H H 5-CH.sub.3 -- CH.sub.3 OCH.sub.312 H H H H H -- CH.sub.3 CH.sub.3 226-23012 H H H H H -- CH.sub.3 OCH.sub.3 180-18213 H H H H 3-CH.sub.3 -- OCH.sub.3 OCH.sub.314 H H H H 3-CH.sub.3 -- CH.sub.3 CH.sub.315 H H H H H -- CH.sub.3 CH.sub.315 H H H H CH.sub.3 -- OCH.sub.3 OCH.sub.316 H H H H H -- CH.sub.3 OCH.sub.317 H 5-F H H -- -- CH.sub.3 CH.sub.318 H H H H CH.sub.3 -- OCH.sub.3 CH.sub.319 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 149-15119 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 173-17520 H H H H H H CH.sub.3 CH.sub.321 H 5-OCH.sub.3 H H H H OCH.sub.3 OCH.sub.322 H 5-CF.sub.3 H H H H CH.sub.3 CH.sub.322 H 5-NO.sub.2 H H H -- CH.sub.3 OCH.sub.323 H H H H H -- OCH.sub.3 OCH.sub.324 H H H H 5-CH.sub.3 -- CH.sub.3 CH.sub.325 H H H H H -- CH.sub.3 CH.sub.325 H H H H CH.sub.3 -- CH.sub.3 OCH.sub.326 H H H H H -- CH.sub.3 CH.sub.327 H 5-NO.sub.2 H H H -- OCH.sub.3 OCH.sub.328 H H H H H -- CH.sub.3 OCH.sub.329 H H H H H -- CH.sub.3 CH.sub.329 H H H H H -- CH.sub.3 OCH.sub.329 H H H H H -- OCH.sub.3 OCH.sub.330 H H H H H -- CH.sub.3 CH.sub.331 H 5-Cl H H H -- CH.sub.3 CH.sub.331 H H H H H -- CH.sub.3 OCH.sub.331 H H H H H -- OCH.sub.3 OCH.sub.332 H H H H H H CH.sub.3 CH.sub.3 192-19432 H H H H H H CH.sub.3 OCH.sub.3 185-18732 H H H H 4-CH.sub.3 H OCH.sub.3 OCH.sub.332 H H H H H H OCH.sub.3 OCH.sub.333 H H H H H -- CH.sub.3 CH.sub.333 H H H H H -- CH.sub.3 OCH.sub.333 H H H H 2-CH.sub.3 -- OCH.sub.3 OCH.sub.334 H H H H 2-CH.sub.3 -- CH.sub.3 OCH.sub.334 H H H H H -- OCH.sub.3 OCH.sub.3 -34 H H H H H -- CH.sub.3 CH.sub.335 H H H H H -- CH.sub.3 CH.sub.3 168-17035 H H H H 5-CH.sub.3 -- CH.sub.3 OCH.sub.335 H H H H H -- CH.sub.3 OCH.sub.3 172-17335 CH.sub.3 H H H H -- OCH.sub.3 OCH.sub.335 H H CH.sub.3 H H -- OCH.sub.3 OCH.sub.335 H H H CH.sub.3 H -- OCH.sub.3 OCH.sub.336 H H H H H -- CH.sub.3 CH.sub.336 H H H H H -- CH.sub.3 OCH.sub.336 H H H H H -- OCH.sub.3 OCH.sub.337 H H H H H -- CH.sub.3 CH.sub.337 H H H H H -- CH.sub.3 OCH.sub.337 H H H H H -- OCH.sub.3 OCH.sub.338 H H H H H -- OCH.sub.3 OCH.sub.338 H H H H CH.sub.3 -- CH.sub.3 OCH.sub. 339 H H H H H -- CH.sub.3 CH.sub.339 H H H H H -- CH.sub.3 OCH.sub.340 H H H H H -- CH.sub.3 CH.sub.340 H H H H H -- CH.sub.3 OCH.sub.341 H H H H 4-Cl -- CH.sub.3 CH.sub.341 H H H H 4-CN -- OCH.sub.3 CH.sub.341 H H H H H -- CH.sub.3 CH.sub.341 H H H H H -- CH.sub.3 OCH.sub.341 H H H H H -- OCH.sub.3 OCH.sub.342 H H H H 4-Cl -- CH.sub.3 OCH.sub.342 H H H H 5-CH.sub.3 -- CH.sub.3 OCH.sub.342 H H H H H -- CH.sub.3 CH.sub.342 H H H H H -- CH.sub.3 OCH.sub.342 H H H H H -- OCH.sub.3 OCH.sub.343 H H H H H H CH.sub.3 CH.sub.3 215-21643 H H H H H H CH.sub.3 OCH.sub.3 206-20743 H H H H H H OCH.sub.3 OCH.sub.343 H H H H 4-CH.sub.3 6-CH.sub.3 CH.sub.3 OCH.sub.343 H H H H 3-Cl 5-CH.sub.3 CH.sub.3 OCH.sub.343 H H H H 3-CH.sub.3 5-CH.sub.3 CH.sub.3 OCH.sub.343 H H H H 4-N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.343 H H H H 5-CN H CH.sub.3 OCH.sub.344 H H H H H H CH.sub.3 CH.sub.344 H H H H H H CH.sub.3 OCH.sub.344 H H H H H H OCH.sub.3 OCH.sub.345 H H H H H H CH.sub.3 CH.sub.345 H H H H H H CH.sub.3 OCH.sub.345 H H H H H H OCH.sub.3 OCH.sub.346 H H H H H H CH.sub.3 CH.sub.346 H H H H H H CH.sub.3 OCH.sub.346 H H H H H H OCH.sub.3 OCH.sub.346 H H H H 5-CH.sub.3 H CH.sub.3 OCH.sub.346 H H H H 5-CH.sub.3 6-CH.sub.3 CH.sub.3 OCH.sub.347 H H H H H H CH.sub. 3 CH.sub.347 H H H H H H CH.sub.3 OCH.sub.347 H H H H H H OCH.sub.3 OCH.sub.347 H H H H 6-CH.sub.3 H CH.sub.3 OCH.sub.347 H H H H 3-CH.sub.3 6-CH.sub.3 CH.sub.3 OCH.sub.348 H H H H 5-CH.sub.3 H CH.sub.3 OCH.sub.348 H H H H 5-Cl H CH.sub.3 OCH.sub.348 H H H H H H CH.sub.3 CH.sub.348 H H H H H H CH.sub.3 OCH.sub.348 H H H H H H OCH.sub.3 OCH.sub.349 H H H H H H CH.sub.3 CH.sub.349 H H H H H H CH.sub.3 OCH.sub.349 H H H H 4-CH.sub.3 6-CH.sub.3 CH.sub.3 CH.sub.3 190-19149 H H H H H H OCH.sub.3 OCH.sub.349 H H H H 4-CH.sub.3 6-CH.sub.3 CH.sub.3 OCH.sub.3 184-18549 H H H H 4-CH.sub.3 6-CH.sub.3 OCH.sub.3 OCH.sub.3 198-19949 H H H H 4-OCH.sub.3 6-OCH.sub.3 CH.sub.3 CH.sub.3 188-19049 H H H H 4-OCH.sub.3 6-OCH.sub.3 CH.sub.3 OCH.sub.3 202-20449 H H H H 4-Cl 6-Cl CH.sub.3 OCH.sub.349 H H H H 4-Cl 4-N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.349 H H H H 4-OCH.sub.3 6-SCH.sub.3 CH.sub.3 OCH.sub.349 H H H H 4-Cl 6-CN CH.sub.3 OCH.sub.350 H H H H H H CH.sub.3 CH.sub.350 H H H H H H CH.sub.3 OCH.sub.350 H H H H H H OCH.sub.3 OCH.sub.350 H H H H 2-CH.sub.3 6-CH.sub.3 CH.sub.3 OCH.sub.350 H H H H 2-CH.sub.3 6-OCH.sub.3 CH.sub.3 OCH.sub.350 H H H H 2-CH.sub.3 6-Cl CH.sub.3 OCH.sub.351 H H H H H H CH.sub.3 CH.sub.351 H H H H H H CH.sub.3 OCH.sub.351 H H H H H H OCH.sub.3 OCH.sub.351 H H H H 2-CH.sub.3 H CH.sub.3 OCH.sub.351 H H H H 5-CH.sub.3 H CH.sub.3 OCH.sub.351 H H H H OCH.sub.3 H CH.sub.3 OCH.sub.352 H H H H H H CH.sub.3 CH.sub.352 H H H H H H CH.sub.3 OCH.sub.352 H H H H H H OCH.sub.3 OCH.sub.352 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.352 H H H H CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.352 H H H H OCH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.353 H H H H H H CH.sub.3 CH.sub.353 H H H H H H CH.sub.3 OCH.sub.353 H H H H H H OCH.sub.3 OCH.sub.353 H H H H 5-CH.sub.3 6-CH.sub.3 OCH.sub.3 OCH.sub.354 H H H H H H CH.sub.3 CH.sub.354 H H H H H H CH.sub.3 OCH.sub.354 H H H H H H OCH.sub.3 OCH.sub.355 H H H H H H CH.sub.3 CH.sub.355 H H H H H H CH.sub.3 OCH.sub.355 H H H H H H OCH.sub.3 OCH.sub.356 H H H H H -- CH.sub.3 CH.sub.356 H H H H H -- CH.sub.3 OCH.sub.356 H H H H H -- OCH.sub.3 OCH.sub.356 H H H H 6-CH.sub.3 -- OCH.sub.3 OCH.sub.357 H H H H H -- CH.sub.3 OCH.sub.357 H H H H 4-CH.sub.3 -- CH.sub.3 OCH.sub.358 H H H H H -- CH.sub.3 OCH.sub.358 H H H H 4-CH.sub.3 -- CH.sub.3 OCH.sub.359 H H H H H -- CH.sub.3 CH.sub.359 H H H H H -- CH.sub.3 OCH.sub.359 H H H H H -- OCH.sub.3 OCH.sub.359 H H H H 4-CH.sub.3 -- OCH.sub.3 OCH.sub.359 H H H H 5-CH.sub.3 -- OCH.sub.3 OCH.sub.360 H H H H 4-CH.sub.3 -- CH.sub.3 OCH.sub.361 H H H H H -- CH.sub.3 OCH.sub.361 H H H H 5-CH.sub.3 -- CH.sub.3 OCH.sub.362 H H H H H -- CH.sub.3 OCH.sub.362 H H H H H -- OCH.sub.3 OCH.sub.363 H H H H H -- CH.sub.3 OCH.sub.363 H H H H H -- OCH.sub.3 OCH.sub.364 H H H H H -- CH.sub.3 OCH.sub.364 H H H H H -- OCH.sub.3 OCH.sub.365 H H H H H -- CH.sub.3 OCH.sub.366 H H H H H -- OCH.sub.3 OCH.sub.367 H H H H H -- CH.sub.3 OCH.sub.367 H H H H H -- OCH.sub.3 OCH.sub.368 H H H H H -- CH.sub.3 OCH.sub.368 H H H H H -- OCH.sub.3 OCH.sub.369 H H H H H -- CH.sub.3 OCH.sub.369 H H H H H -- OCH.sub.3 OCH.sub.370 H H H H H -- CH.sub.3 OCH.sub.370 H H H H H -- OCH.sub.3 OCH.sub.371 H H H H H H CH.sub.3 CH.sub.371 H H H H H H CH.sub.3 OCH.sub. 371 H H H H H H OCH.sub.3 OCH.sub.371 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.371 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.371 H H H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.371 H H H H CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.371 H H H H OCH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.372 H H H H H H CH.sub.3 CH.sub.372 H H H H H H CH.sub.3 OCH.sub.372 H H H H H H OCH.sub.3 OCH.sub.372 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.372 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.372 H H H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.372 H H H H CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.372 H H H H OCH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.373 H H H H H H CH.sub.3 CH.sub.373 H H H H H H CH.sub.3 OCH.sub.373 H H H H H H OCH.sub.3 OCH.sub.373 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.373 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.373 H H H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.373 H H H H CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.373 H H H H OCH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.374 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.374 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.374 H H H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.332 H H H H H H Cl OCH.sub.332 H H H H H H OCH.sub.3 C.sub.2 H.sub.532 H H H H H H OCH.sub.3 OC.sub.2 H.sub.532 H H H H H H OCH.sub.3 CH.sub.2 OCH.sub.335 H H H H H -- Cl CH.sub.335 H H H H H -- CH.sub.3 C.sub.2 H.sub.535 H H H H H -- CH.sub.3 OC.sub.2 H.sub.535 H H H H H -- CH.sub.3 CH.sub.2 OCH.sub.335 H H H H H -- CH.sub.3 H32 H H H H H -- Cl NH.sub.232 H H H H H -- Cl NHCH.sub.335 H H H H H -- Cl N(CH.sub.3).sub.2__________________________________________________________________________
TABLE III__________________________________________________________________________ ##STR92##A R R.sub.1 R.sub.2 R.sub.3 R.sub.5 R.sub.6 X Y m.p. (.degree.C.)__________________________________________________________________________1 H H H H H H CH.sub.3 CH.sub.31 H H H H 4-CH.sub.3 H CH.sub.3 CH.sub.32 H H H H H H CH.sub.3 OCH.sub.32 H H H H 5-CH.sub.3 H CH.sub.3 CH.sub.33 H H H H 2-CH.sub.3 5-CH.sub.3 CH.sub.3 OCH.sub.33 H H H H H H CH.sub.3 OCH.sub.34 H H H H H H OCH.sub.3 OCH.sub.35 H H H H H H CH.sub.3 OCH.sub.35 H 5-Cl H H H H OCH.sub.3 OCH.sub.36 H H H H H H CH.sub.3 CH.sub.36 H H H H H H CH.sub.3 OCH.sub.3 194-1977 H H H H 3-CH.sub.3 4-CH.sub.3 CH.sub.3 CH.sub.38 H 5-F H H H H OCH.sub.3 OCH.sub.38 H 5-Br H H 4-CH.sub.3 H CH.sub.3 OCH.sub.39 H H H H H H CH.sub.3 CH.sub.310 H H H H H H CH.sub.3 OCH.sub.311 H H H H H H OCH.sub.3 OCH.sub.312 H H H H 5-SCH.sub.3 -- CH.sub.3 CH.sub.312 H H H H 5-CH.sub.3 -- CH.sub.3 OCH.sub.312 H H H H H -- CH.sub.3 CH.sub.312 H H H H H -- CH.sub.3 OCH.sub.3 176-17913 H H H H 3-CH.sub.3 -- OCH.sub.3 OCH.sub.314 H H H H 3-CH.sub.3 -- CH.sub.3 CH.sub.315 H H H H H -- CH.sub.3 CH.sub.315 H H H H CH.sub.3 -- OCH.sub. 3 OCH.sub.316 H H H H H -- CH.sub.3 OCH.sub.317 H 5-F H H -- -- CH.sub.3 CH.sub.318 H H H H CH.sub.3 -- OCH.sub.3 CH.sub.319 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.319 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 142-14420 H H H H H H CH.sub.3 CH.sub.321 H 5-OCH.sub.3 H H H H OCH.sub.3 OCH.sub.322 H 5-CF.sub.3 H H H H CH.sub.3 CH.sub.322 H 5-NO.sub.2 H H H -- CH.sub.3 OCH.sub.323 H H H H H -- OCH.sub.3 OCH.sub.324 H H H H 5-CH.sub.3 -- CH.sub.3 CH.sub.325 H H H H H -- CH.sub.3 CH.sub.325 H H H H CH.sub.3 -- CH.sub.3 OCH.sub.326 H H H H H -- CH.sub.3 CH.sub.327 H 5-NO.sub.2 H H H -- OCH.sub.3 OCH.sub.328 H H H H H -- CH.sub.3 OCH.sub.329 H H H H H -- CH.sub.3 CH.sub.329 H H H H H -- CH.sub.3 OCH.sub.329 H H H H H -- OCH.sub.3 OCH.sub.330 H H H H H -- CH.sub.3 CH.sub.331 H 5-Cl H H H -- CH.sub.3 CH.sub.331 H H H H H -- CH.sub.3 OCH.sub.331 H H H H H -- OCH.sub.3 OCH.sub.332 H H H H H H CH.sub.3 CH.sub.332 H H H H H H CH.sub.3 OCH.sub.332 H H H H 4-CH.sub.3 H OCH.sub.3 OCH.sub.332 H H H H H H OCH.sub.3 OCH.sub.333 H H H H H -- CH.sub.3 CH.sub.333 H H H H H -- CH.sub.3 OCH.sub.333 H H H H 2-CH.sub.3 -- OCH.sub.3 OCH.sub.334 H H H H 2-CH.sub.3 -- CH.sub.3 OCH.sub.334 H H H H H -- OCH.sub.3 OCH.sub.334 H H H H H -- CH.sub.3 CH.sub.335 H H H H H -- CH.sub.3 CH.sub.335 H H H H 5-CH.sub.3 -- CH.sub.3 OCH.sub.335 H H H H H -- CH.sub.3 OCH.sub.335 CH.sub.3 H H H H -- OCH.sub.3 OCH.sub.335 H H CH.sub.3 H H -- OCH.sub.3 OCH.sub.335 H H H CH.sub.3 H -- OCH.sub.3 OCH.sub.336 H H H H H -- CH.sub.3 CH.sub.336 H H H H H -- CH.sub.3 OCH.sub.336 H H H H H -- OCH.sub.3 OCH.sub.337 H H H H H -- CH.sub.3 CH.sub.337 H H H H H -- CH.sub.3 OCH.sub.337 H H H H H -- OCH.sub.3 OCH.sub.338 H H H H H -- OCH.sub.3 OCH.sub.338 H H H H CH.sub.3 -- CH.sub.3 OCH.sub.339 H H H H H -- CH.sub.3 CH.sub.339 H H H H H -- CH.sub.3 OCH.sub.340 H H H H H -- CH.sub.3 CH.sub.340 H H H H H -- CH.sub.3 OCH.sub.341 H H H H 4-Cl -- CH.sub.3 CH.sub.341 H H H H 4-CN -- OCH.sub.3 CH.sub.341 H H H H H -- CH.sub.3 CH.sub.341 H H H H H -- CH.sub.3 OCH.sub.341 H H H H H -- OCH.sub.3 OCH.sub.342 H H H H 4-Cl -- CH.sub.3 OCH.sub.342 H H H H 5-CH.sub.3 -- CH.sub.3 OCH.sub.342 H H H H H -- CH.sub.3 CH.sub.342 H H H H H -- CH.sub.3 OCH.sub.342 H H H H H -- OCH.sub.3 OCH.sub.343 H H H H H H CH.sub.3 CH.sub.343 H H H H H H CH.sub.3 OCH.sub.3 161-16343 H H H H H H OCH.sub.3 OCH.sub.343 H H H H 4-CH.sub.3 6-CH.sub.3 CH.sub.3 OCH.sub.343 H H H H 3-Cl 5-CH.sub.3 CH.sub.3 OCH.sub.343 H H H H 3-CH.sub.3 5-CH.sub.3 CH.sub.3 OCH.sub.343 H H H H 4-N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.343 H H H H 5-CN H CH.sub.3 OCH.sub.344 H H H H H H CH.sub.3 CH.sub.344 H H H H H H CH.sub.3 OCH.sub.344 H H H H H H OCH.sub.3 OCH.sub.345 H H H H H H CH.sub.3 CH.sub.345 H H H H H H CH.sub.3 OCH.sub.345 H H H H H H OCH.sub.3 OCH.sub.346 H H H H H H CH.sub.3 CH.sub.346 H H H H H H CH.sub.3 OCH.sub.346 H H H H H H OCH.sub.3 OCH.sub.346 H H H H 5-CH.sub.3 H CH.sub.3 OCH.sub.346 H H H H 5-CH.sub.3 6-CH.sub.3 CH.sub.3 OCH.sub.347 H H H H H H CH.sub.3 CH.sub.347 H H H H H H CH.sub.3 OCH.sub.347 H H H H H H OCH.sub.3 OCH.sub.347 H H H H 6-CH.sub.3 H CH.sub.3 OCH.sub.347 H H H H 3-CH.sub.3 6-CH.sub.3 CH.sub.3 OCH.sub.348 H H H H 5-CH.sub.3 H CH.sub.3 OCH.sub.348 H H H H 5-Cl H CH.sub.3 OCH.sub.348 H H H H H H CH.sub.3 CH.sub.348 H H H H H H CH.sub.3 OCH.sub.348 H H H H H H OCH.sub.3 OCH.sub.349 H H H H H H CH.sub.3 CH.sub.349 H H H H H H CH.sub.3 OCH.sub.349 H H H H 4-CH.sub.3 6-CH.sub.3 CH.sub.3 CH.sub.349 H H H H H H OCH.sub.3 OCH.sub.349 H H H H 4-CH.sub.3 6-CH.sub.3 CH.sub.3 OCH.sub.3 172-17349 H H H H 4-CH.sub.3 6-CH.sub.3 OCH.sub.3 OCH.sub.349 H H H H 4-OCH.sub.3 6-OCH.sub.3 CH.sub.3 CH.sub.349 H H H H 4-OCH.sub.3 6-OCH.sub.3 CH.sub.3 OCH.sub.3 194-19649 H H H H 4-Cl 6-Cl CH.sub.3 OCH.sub.349 H H H H 4-Cl 4-N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.349 H H H H 4-OCH.sub.3 6-SCH.sub.3 CH.sub.3 OCH.sub.349 H H H H 4-Cl 6-CN CH.sub.3 OCH.sub.350 H H H H H H CH.sub.3 CH.sub.350 H H H H H H CH.sub.3 OCH.sub.350 H H H H H H OCH.sub.3 OCH.sub.350 H H H H 2-CH.sub.3 6-CH.sub.3 CH.sub.3 OCH.sub.350 H H H H 2-CH.sub.3 6-OCH.sub.3 CH.sub.3 OCH.sub.350 H H H H 2-CH.sub.3 6-Cl CH.sub.3 OCH.sub.351 H H H H H H CH.sub.3 CH.sub.351 H H H H H H CH.sub.3 OCH.sub.351 H H H H H H OCH.sub.3 OCH.sub.351 H H H H 2-CH.sub.3 H CH.sub.3 OCH.sub.351 H H H H 5-CH.sub.3 H CH.sub.3 OCH.sub.351 H H H H OCH.sub.3 H CH.sub.3 OCH.sub.352 H H H H H H CH.sub.3 CH.sub.352 H H H H H H CH.sub.3 OCH.sub.352 H H H H H H OCH.sub.3 OCH.sub.352 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.352 H H H H CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.352 H H H H OCH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.353 H H H H H H CH.sub.3 CH.sub.353 H H H H H H CH.sub.3 OCH.sub.353 H H H H H H OCH.sub.3 OCH.sub.353 H H H H 5-CH.sub.3 6-CH.sub.3 OCH.sub.3 OCH.sub.354 H H H H H H CH.sub.3 CH.sub.354 H H H H H H CH.sub.3 OCH.sub.354 H H H H H H OCH.sub.3 OCH.sub.355 H H H H H H CH.sub.3 CH.sub.355 H H H H H H CH.sub.3 OCH.sub.355 H H H H H H OCH.sub.3 OCH.sub.356 H H H H H -- CH.sub.3 CH.sub.356 H H H H H -- CH.sub.3 OCH.sub.356 H H H H H -- OCH.sub.3 OCH.sub.356 H H H H 6-CH.sub.3 -- OCH.sub.3 OCH.sub.357 H H H H H -- CH.sub.3 OCH.sub.357 H H H H 4-CH.sub.3 -- CH.sub.3 OCH.sub.358 H H H H H -- CH.sub.3 OCH.sub.358 H H H H 4-CH.sub.3 -- CH.sub.3 OCH.sub.359 H H H H H -- CH.sub.3 CH.sub.359 H H H H H -- CH.sub.3 OCH.sub.359 H H H H H -- OCH.sub.3 OCH.sub.359 H H H H 4-CH.sub.3 -- OCH.sub.3 OCH.sub.359 H H H H 5-CH.sub.3 -- OCH.sub.3 OCH.sub.360 H H H H 4-CH.sub.3 -- CH.sub.3 OCH.sub.361 H H H H H -- CH.sub.3 OCH.sub.361 H H H H 5-CH.sub.3 -- CH.sub.3 OCH.sub.362 H H H H H -- CH.sub.3 OCH.sub.362 H H H H H -- OCH.sub.3 OCH.sub.363 H H H H H -- CH.sub.3 OCH.sub.363 H H H H H -- OCH.sub.3 OCH.sub.364 H H H H H -- CH.sub.3 OCH.sub.364 H H H H H -- OCH.sub.3 OCH.sub.365 H H H H H -- CH.sub.3 OCH.sub.366 H H H H H -- OCH.sub.3 OCH.sub.367 H H H H H -- CH.sub.3 OCH.sub.367 H H H H H -- OCH.sub.3 OCH.sub.368 H H H H H -- CH.sub.3 OCH.sub.368 H H H H H -- OCH.sub.3 OCH.sub.369 H H H H H -- CH.sub.3 OCH.sub.369 H H H H H -- OCH.sub.3 OCH.sub.370 H H H H H -- CH.sub.3 OCH.sub.370 H H H H H -- OCH.sub.3 OCH.sub.371 H H H H H H CH.sub.3 CH.sub.371 H H H H H H CH.sub.3 OCH.sub.371 H H H H H H OCH.sub.3 OCH.sub.371 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.371 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.371 H H H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.371 H H H H CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.371 H H H H OCH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.372 H H H H H H CH.sub.3 CH.sub.372 H H H H H H CH.sub.3 OCH.sub.372 H H H H H H OCH.sub.3 OCH.sub.372 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.372 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.372 H H H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.372 H H H H CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.372 H H H H OCH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.373 H H H H H H CH.sub.3 CH.sub.373 H H H H H H CH.sub.3 OCH.sub.373 H H H H H H OCH.sub.3 OCH.sub.373 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.373 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.373 H H H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.373 H H H H CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.373 H H H H OCH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.374 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.374 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.374 H H H H CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.332 H H H H H H OCH.sub.3 C.sub.2 H.sub.532 H H H H H H OCH.sub.3 OC.sub.2 H.sub.532 H H H H H H OCH.sub.3 CH.sub.2 OCH.sub.335 H H H H H -- CH.sub.3 C.sub.2 H.sub.535 H H H H H -- CH.sub.3 OC.sub.2 H.sub.535 H H H H H -- CH.sub.3 CH.sub.2 OCH.sub.335 H H H H H -- CH.sub.3 H__________________________________________________________________________
TABLE IV__________________________________________________________________________ ##STR93##A R R.sub.1 R.sub.2 R.sub.3 R.sub.5 R.sub.6 X Y m.p. (.degree.C.)__________________________________________________________________________1 H H H H H H CH.sub.3 CH.sub.31 H H H H 4-CH.sub.3 H CH.sub.3 CH.sub.32 H H H H H H CH.sub.3 OCH.sub.32 H H H H 5-CH.sub.3 H CH.sub.3 CH.sub.33 H H H H 2-CH.sub.3 5-CH.sub.3 CH.sub.3 OCH.sub.33 H H H H H H CH.sub.3 OCH.sub.34 H H H H H H CH.sub.3 CH.sub.35 H H H H H H CH.sub.3 OCH.sub.35 H 5-Cl H H H H CH.sub.3 H6 H H H H H H CH.sub.3 CH.sub.36 H H H H H H CH.sub.3 OCH.sub.37 H H H H 3-CH.sub.3 4-CH.sub.3 CH.sub.3 CH.sub.38 H 5-F H H H H CH.sub.3 CH.sub.38 H 5-Br H H 4-CH.sub.3 H CH.sub.3 OCH.sub.39 H H H H H H CH.sub.3 CH.sub.310 H H H H H H CH.sub.3 OCH.sub.311 H H H H H H CH.sub.3 CH.sub.312 H H H H 5-SCH.sub.3 -- CH.sub.3 CH.sub.312 H H H H 5-CH.sub.3 -- CH.sub.3 H12 H H H H H -- CH.sub.3 CH.sub.312 H H H H H -- CH.sub.3 OCH.sub.313 H H H H 3-CH.sub.3 -- CH.sub.3 H14 H H H H 3-CH.sub.3 -- CH.sub.3 CH.sub.315 H H H H H -- CH.sub.3 CH.sub.315 H H H H CH.sub.3 -- CH.sub.3 OCH.sub.316 H H H H H -- CH.sub.3 OCH.sub.317 H 5-F H H -- -- CH.sub.3 CH.sub.318 H H H H CH.sub.3 -- OCH.sub.3 CH.sub.319 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.319 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.320 H H H H H H CH.sub.3 CH.sub.321 H 5-OCH.sub.3 H H H H CH.sub.3 OCH.sub.322 H 5-CF.sub.3 H H H H CH.sub.3 CH.sub.322 H 5-NO.sub.2 H H H -- CH.sub.3 OCH.sub.323 H H H H H -- CH.sub.3 H24 H H H H 5-CH.sub.3 -- CH.sub.3 CH.sub.325 H H H H H -- CH.sub.3 CH.sub.325 H H H H CH.sub.3 -- CH.sub.3 OCH.sub.326 H H H H H -- CH.sub.3 CH.sub.327 H 5-NO.sub.2 H H H -- OCH.sub.3 CH.sub.328 H H H H H -- CH.sub.3 OCH.sub.329 H H H H H -- CH.sub.3 CH.sub.329 H H H H H -- CH.sub.3 OCH.sub.329 H H H H H -- OCH.sub.3 OCH.sub.330 H H H H H -- CH.sub.3 CH.sub.331 H 5-Cl H H H -- CH.sub.3 CH.sub.331 H H H H H -- CH.sub.3 OCH.sub.331 H H H H H -- OCH.sub.3 OCH.sub.332 H H H H H H CH.sub.3 CH.sub.332 H H H H H H CH.sub.3 OCH.sub.332 H H H H 4-CH.sub.3 H CH.sub.3 H32 H H H H H H CH.sub.3 H33 H H H H H -- CH.sub.3 CH.sub.333 H H H H H -- CH.sub.3 OCH.sub.333 H H H H 2-CH.sub.3 -- OCH.sub.3 OCH.sub.334 H H H H 2-CH.sub.3 -- CH.sub.3 OCH.sub.334 H H H H H -- CH.sub.3 H34 H H H H H -- CH.sub.3 CH.sub.335 H H H H H -- CH.sub.3 CH.sub.335 H H H H 5-CH.sub.3 -- CH.sub.3 OCH.sub.335 H H H H H -- CH.sub.3 OCH.sub.335 CH.sub.3 H H H H -- CH.sub.3 H35 H H CH.sub.3 H H -- CH.sub.3 CH.sub.335 H H H CH.sub.3 H -- CH.sub.3 CH.sub.336 H H H H H -- CH.sub.3 CH.sub.336 H H H H H -- CH.sub.3 OCH.sub.336 H H H H H -- OCH.sub.3 OCH.sub.337 H H H H H -- CH.sub.3 CH.sub.337 H H H H H -- CH.sub.3 OCH.sub.337 H H H H H -- OCH.sub.3 OCH.sub.338 H H H H H -- OCH.sub.3 OCH.sub.338 H H H H CH.sub.3 -- CH.sub.3 OCH.sub.339 H H H H H -- CH.sub.3 CH.sub.339 H H H H H -- CH.sub.3 OCH.sub.340 H H H H H -- CH.sub.3 CH.sub.340 H H H H H -- CH.sub.3 OCH.sub.341 H H H H 4-Cl -- CH.sub.3 CH.sub.341 H H H H 4-CN -- OCH.sub.3 CH.sub.341 H H H H H -- OCH.sub.3 OCH.sub.341 H H H H H -- CH.sub.3 CH.sub.341 H H H H H -- CH.sub.3 OCH.sub.341 H H H H H -- CH.sub.3 H42 H H H H 4-Cl -- CH.sub.3 OCH.sub.342 H H H H 5-CH.sub.3 -- CH.sub.3 OCH.sub.342 H H H H H -- CH.sub.3 CH.sub.342 H H H H H -- CH.sub.3 OCH.sub.342 H H H H H -- OCH.sub.3 OCH.sub.343 H H H H H H CH.sub.3 CH.sub.343 H H H H H H CH.sub.3 OCH.sub.343 H H H H H H CH.sub.3 H43 H H H H 4-CH.sub.3 6-CH.sub.3 CH.sub.3 CH.sub.343 H H H H 3-Cl 5-CH.sub.3 CH.sub.3 CH.sub.343 H H H H 3-CH.sub.3 5-CH.sub.3 CH.sub.3 CH.sub.343 H H H H 4-N(CH.sub.3).sub.2 H CH.sub.3 CH.sub.343 H H H H 5-CN H CH.sub.3 CH.sub.344 H H H H H H CH.sub.3 CH.sub.344 H H H H H H CH.sub.3 OCH.sub.344 H H H H H H OCH.sub.3 OCH.sub.345 H H H H H H CH.sub.3 CH.sub.345 H H H H H H CH.sub.3 OCH.sub.345 H H H H H H OCH.sub.3 OCH.sub.346 H H H H H H CH.sub.3 CH.sub.346 H H H H H H CH.sub.3 OCH.sub.346 H H H H H H OCH.sub.3 OCH.sub.346 H H H H 5-CH.sub.3 H CH.sub.3 CH.sub.346 H H H H 5-CH.sub.3 6-CH.sub.3 CH.sub.3 H47 H H H H H H CH.sub.3 CH.sub.347 H H H H H H CH.sub.3 OCH.sub.347 H H H H H H OCH.sub.3 OCH.sub.347 H H H H 6-CH.sub.3 H CH.sub.3 OCH.sub.347 H H H H 3-CH.sub.3 6-CH.sub.3 CH.sub.3 H48 H H H H 5-CH.sub.3 H CH.sub.3 CH.sub.348 H H H H 5-Cl H CH.sub.3 OCH.sub.348 H H H H H H CH.sub.3 CH.sub.348 H H H H H H CH.sub.3 OCH.sub.348 H H H H H H CH.sub.3 H49 H H H H H H CH.sub.3 CH.sub.349 H H H H H H CH.sub.3 OCH.sub.349 H H H H 4-CH.sub.3 6-CH.sub.3 CH.sub.3 CH.sub.349 H H H H H H OCH.sub.3 OCH.sub.349 H H H H 4-CH.sub.3 6-CH.sub.3 CH.sub.3 OCH.sub.349 H H H H 4-CH.sub.3 6-CH.sub.3 CH.sub.3 H49 H H H H 4-OCH.sub.3 6-OCH.sub.3 CH.sub.3 CH.sub.349 H H H H 4-OCH.sub.3 6-OCH.sub.3 CH.sub.3 OCH.sub.349 H H H H 4-Cl 6-Cl CH.sub.3 H49 H H H H 4-Cl 4-N(CH.sub.3).sub. 2 CH.sub.3 H49 H H H H 4-OCH.sub.3 6-SCH.sub.3 CH.sub.3 CH.sub.349 H H H H 4-Cl 6-CN CH.sub.3 CH.sub.350 H H H H H H CH.sub.3 CH.sub.350 H H H H H H CH.sub.3 OCH.sub.350 H H H H H H OCH.sub.3 OCH.sub.350 H H H H 2-CH.sub.3 6-CH.sub.3 CH.sub.3 CH.sub.350 H H H H 2-CH.sub.3 6-OCH.sub.3 CH.sub.3 CH.sub.350 H H H H 2-CH.sub.3 6-Cl CH.sub.3 OCH.sub.351 H H H H H H CH.sub.3 CH.sub.351 H H H H H H CH.sub.3 OCH.sub.351 H H H H H H OCH.sub.3 OCH.sub.351 H H H H 2-CH.sub.3 H CH.sub.3 OCH.sub.351 H H H H 5-CH.sub.3 H CH.sub.3 H51 H H H H OCH.sub.3 H CH.sub.3 OCH.sub.352 H H H H H H CH.sub.3 CH.sub.352 H H H H H H CH.sub.3 OCH.sub.352 H H H H H H OCH.sub.3 OCH.sub.352 H H H H CH.sub.3 CH.sub.3 CH.sub.3 H52 H H H H CH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.352 H H H H OCH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.353 H H H H H H CH.sub.3 CH.sub.353 H H H H H H CH.sub.3 OCH.sub.353 H H H H H H CH.sub.3 H53 H H H H 5-CH.sub.3 6-CH.sub.3 CH.sub.3 CH.sub.354 H H H H H H CH.sub.3 CH.sub.354 H H H H H H CH.sub.3 OCH.sub.354 H H H H H H CH.sub.3 H55 H H H H H H CH.sub.3 CH.sub.355 H H H H H H CH.sub.3 OCH.sub.355 H H H H H H CH.sub.3 H56 H H H H H -- CH.sub.3 CH.sub.356 H H H H H -- CH.sub.3 OCH.sub.356 H H H H H -- OCH.sub.3 OCH.sub.356 H H H H 6-CH.sub.3 -- CH.sub.3 CH.sub.357 H H H H H -- CH.sub.3 OCH.sub.357 H H H H 4-CH.sub.3 -- CH.sub.3 CH.sub.358 H H H H H -- CH.sub.3 OCH.sub.358 H H H H 4-CH.sub.3 -- CH.sub.3 CH.sub.359 H H H H H -- CH.sub.3 CH.sub.359 H H H H H -- CH.sub.3 OCH.sub.359 H H H H H -- OCH.sub.3 OCH.sub.359 H H H H 4-CH.sub.3 -- CH.sub.3 CH.sub.359 H H H H 5-CH.sub.3 -- CH.sub.3 H60 H H H H 4-CH.sub.3 -- CH.sub.3 CH.sub.361 H H H H H -- CH.sub.3 OCH.sub.361 H H H H 5-CH.sub.3 -- CH.sub.3 CH.sub.362 H H H H H -- CH.sub.3 OCH.sub.362 H H H H H -- OCH.sub.3 OCH.sub.363 H H H H H -- CH.sub.3 OCH.sub.363 H H H H H -- CH.sub.3 CH.sub.364 H H H H H -- CH.sub.3 OCH.sub.364 H H H H H -- CH.sub.3 CH.sub.365 H H H H H -- CH.sub.3 OCH.sub.366 H H H H H -- CH.sub.3 CH.sub.367 H H H H H -- CH.sub.3 OCH.sub.367 H H H H H -- CH.sub.3 CH.sub.368 H H H H H -- CH.sub.3 OCH.sub.368 H H H H H -- CH.sub.3 CH.sub.369 H H H H H -- CH.sub.3 OCH.sub.369 H H H H H -- CH.sub.3 CH.sub.370 H H H H H -- CH.sub.3 OCH.sub.370 H H H H H -- CH.sub.3 CH.sub.371 H H H H H H CH.sub.3 CH.sub.371 H H H H H H CH.sub.3 OCH.sub.371 H H H H H H OCH.sub.3 OCH.sub.371 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.371 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.371 H H H H CH.sub.3 CH.sub.3 CH.sub.3 H71 H H H H CH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.371 H H H H OCH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.372 H H H H H H CH.sub.3 CH.sub.372 H H H H H H CH.sub.3 OCH.sub.372 H H H H H H OCH.sub.3 OCH.sub.372 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.372 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.372 H H H H CH.sub.3 CH.sub.3 CH.sub.3 H72 H H H H CH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.372 H H H H OCH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.373 H H H H H H CH.sub.3 CH.sub.373 H H H H H H CH.sub.3 OCH.sub.373 H H H H H H OCH.sub.3 OCH.sub.373 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.373 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.373 H H H H CH.sub.3 CH.sub.3 CH.sub. 3 H73 H H H H CH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.373 H H H H OCH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.374 H H H H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.374 H H H H CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.374 H H H H CH.sub.3 CH.sub.3 CH.sub.3 H32 H H H H H H OCH.sub.3 C.sub.2 H.sub.532 H H H H H H OCH.sub.3 OC.sub.2 H.sub.532 H H H H H H OCH.sub.3 CH.sub.2 OCH.sub.335 H H H H H -- CH.sub.3 C.sub.2 H.sub.535 H H H H H -- CH.sub.3 OC.sub.2 H.sub.535 H H H H H -- CH.sub.3 CH.sub.2 OCH.sub.3__________________________________________________________________________
TABLE V__________________________________________________________________________ ##STR94##A R R.sub.1 R.sub.2 R.sub.3 R.sub.5 R.sub.6 Y.sub.1 m.p. (.degree.C.)__________________________________________________________________________ 1 H H H H H H CH.sub.3 1 H H H H 4-CH.sub.3 H CH.sub.3 2 H H H H H H OCH.sub.3 2 H H H H 5-CH.sub.3 H CH.sub.3 3 H H H H 2-CH.sub.3 5-CH.sub.3 OCH.sub.3 3 H H H H H H OCH.sub.3 4 H H H H H H OCH.sub.3 5 H H H H H H OCH.sub.3 5 H 5-Cl H H H H OCH.sub.3 6 H H H H H H CH.sub.3 6 H H H H H H OCH.sub.3 7 H H H H 3-CH.sub.3 4-CH.sub.3 CH.sub.3 8 H 5-F H H H H OCH.sub.3 8 H 5-Br H H 4-CH.sub.3 H OCH.sub.3 9 H H H H H H CH.sub.310 H H H H H H OCH.sub.311 H H H H H H OCH.sub.312 H H H H 5-SCH.sub.3 -- CH.sub.312 H H H H 5-CH.sub.3 -- OCH.sub.312 H H H H H -- CH.sub.312 H H H H H -- OCH.sub.313 H H H H 3-CH.sub.3 -- OCH.sub.314 H H H H 3-CH.sub.3 -- CH.sub.315 H H H H H -- CH.sub.315 H H H H CH.sub.3 -- OCH.sub.316 H H H H H -- OCH.sub.317 H 5-F H H -- -- CH.sub.318 H H H H CH.sub. 3 -- CH.sub.319 H H H H CH.sub.3 CH.sub.3 CH.sub.319 H H H H CH.sub.3 CH.sub.3 OCH.sub.320 H H H H H H CH.sub.321 H 5-OCH.sub.3 H H H H OCH.sub.322 H 5-CF.sub.3 H H H H CH.sub.322 H 5-NO.sub.2 H H H -- OCH.sub.323 H H H H H -- OCH.sub.324 H H H H 5-CH.sub.3 -- CH.sub.325 H H H H H -- CH.sub.325 H H H H CH.sub.3 -- OCH.sub.326 H H H H H -- CH.sub.327 H 5-NO.sub.2 H H H -- OCH.sub.328 H H H H H -- OCH.sub.329 H H H H H -- CH.sub.329 H H H H H -- OCH.sub.330 H H H H H -- CH.sub.331 H 5-Cl H H H -- CH.sub.331 H H H H H -- CH.sub.331 H H H H H -- OCH.sub.332 H H H H H H CH.sub.332 H H H H H H OCH.sub.332 H H H H 4-CH.sub.3 H OCH.sub.333 H H H H H -- CH.sub.333 H H H H H -- OCH.sub.333 H H H H 2-CH.sub.3 -- OCH.sub.334 H H H H 2-CH.sub.3 -- OCH.sub.334 H H H H H -- OCH.sub.334 H H H H H -- CH.sub.335 H H H H H -- CH.sub.335 H H H H 5-CH.sub.3 -- OCH.sub.335 H H H H H -- OCH.sub.335 CH.sub.3 H H H H -- OCH.sub.335 H H CH.sub.3 H H -- OCH.sub.335 H H H CH.sub.3 H -- OCH.sub.336 H H H H H -- CH.sub.336 H H H H H -- OCH.sub.337 H H H H H -- CH.sub.337 H H H H H -- OCH.sub.338 H H H H H -- OCH.sub.338 H H H H CH.sub.3 -- OCH.sub.339 H H H H H -- CH.sub.339 H H H H H -- OCH.sub.340 H H H H H -- CH.sub.340 H H H H H -- OCH.sub.341 H H H H 4-Cl -- CH.sub.341 H H H H 4-CN -- CH.sub.341 H H H H H -- CH.sub.341 H H H H H -- OCH.sub.342 H H H H 4-Cl -- OCH.sub.342 H H H H 5-CH.sub.3 -- OCH.sub.342 H H H H H -- CH.sub.342 H H H H H -- OCH.sub.343 H H H H H H CH.sub.343 H H H H H H OCH.sub.343 H H H H 4-CH.sub.3 6-CH.sub.3 OCH.sub.343 H H H H 3-Cl 5-CH.sub.3 OCH.sub.343 H H H H 3-CH.sub.3 5-CH.sub.3 OCH.sub.343 H H H H 4-N(CH.sub.3).sub.2 H OCH.sub.343 H H H H 5-CN H OCH.sub.344 H H H H H H CH.sub.344 H H H H H H OCH.sub.345 H H H H H H CH.sub.345 H H H H H H OCH.sub.346 H H H H H H CH.sub.346 H H H H H H OCH.sub.346 H H H H 5-CH.sub.3 H OCH.sub.346 H H H H 5-CH.sub.3 6-CH.sub.3 OCH.sub.347 H H H H H H CH.sub.347 H H H H H H OCH.sub.347 H H H H 6-CH.sub.3 H OCH.sub.347 H H H H 3-CH.sub.3 6-CH.sub.3 OCH.sub.348 H H H H 5-CH.sub.3 H OCH.sub.348 H H H H 5-Cl H OCH.sub.348 H H H H H H CH.sub.348 H H H H H H OCH.sub.349 H H H H H H CH.sub.349 H H H H H H OCH.sub.349 H H H H 4-CH.sub.3 6-CH.sub.3 CH.sub.349 H H H H 4-CH.sub.3 6-CH.sub.3 OCH.sub.349 H H H H 4-OCH.sub.3 6-OCH.sub.3 CH.sub.349 H H H H 4-OCH.sub.3 6-OCH.sub.3 OCH.sub.349 H H H H 4-Cl 6-Cl OCH.sub.349 H H H H 4-Cl 4-N(CH.sub.3).sub.2 OCH.sub.349 H H H H 4-OCH.sub.3 6-SCH.sub.3 OCH.sub.349 H H H H 4-Cl 6-CN OCH.sub.350 H H H H H H CH.sub.350 H H H H H H OCH.sub.350 H H H H 2-CH.sub.3 6-CH.sub.3 OCH.sub.350 H H H H 2-CH.sub.3 6-OCH.sub.3 OCH.sub.350 H H H H 2-CH.sub.3 6-Cl OCH.sub.351 H H H H H H CH.sub.351 H H H H H H OCH.sub.351 H H H H 2-CH.sub.3 H OCH.sub.351 H H H H 5-CH.sub.3 H OCH.sub.351 H H H H OCH.sub.3 H OCH.sub.352 H H H H H H CH.sub.352 H H H H H H OCH.sub.352 H H H H CH.sub.3 CH.sub.3 OCH.sub.352 H H H H CH.sub.3 OCH.sub.3 OCH.sub.352 H H H H OCH.sub.3 OCH.sub.3 OCH.sub.353 H H H H H H CH.sub.353 H H H H H H OCH.sub.353 H H H H 5-CH.sub.3 6-CH.sub.3 OCH.sub.354 H H H H H H CH.sub.354 H H H H H H OCH.sub.355 H H H H H H CH.sub.355 H H H H H H OCH.sub.356 H H H H H -- CH.sub.356 H H H H H -- OCH.sub.356 H H H H 6-CH.sub.3 -- OCH.sub.357 H H H H H -- OCH.sub.357 H H H H 4-CH.sub.3 -- OCH.sub.358 H H H H H -- OCH.sub.358 H H H H 4-CH.sub.3 -- OCH.sub.359 H H H H H -- CH.sub.359 H H H H H -- OCH.sub.359 H H H H 4-CH.sub.3 -- OCH.sub.359 H H H H 5-CH.sub.3 -- OCH.sub.360 H H H H 4-CH.sub.3 -- OCH.sub. 361 H H H H H -- OCH.sub.361 H H H H 5-CH.sub.3 -- OCH.sub.362 H H H H H -- CH.sub.362 H H H H H -- OCH.sub.363 H H H H H -- CH.sub.363 H H H H H -- OCH.sub.364 H H H H H -- CH.sub.364 H H H H H -- OCH.sub.365 H H H H H -- OCH.sub.366 H H H H H -- OCH.sub.367 H H H H H -- CH.sub.367 H H H H H -- OCH.sub.368 H H H H H -- CH.sub.368 H H H H H -- OCH.sub.369 H H H H H -- CH.sub.369 H H H H H -- OCH.sub.370 H H H H H -- CH.sub.370 H H H H H -- OCH.sub.371 H H H H H H CH.sub.371 H H H H H H OCH.sub.371 H H H H CH.sub.3 CH.sub.3 CH.sub.371 H H H H CH.sub.3 CH.sub.3 OCH.sub.371 H H H H CH.sub.3 OCH.sub.3 OCH.sub.371 H H H H OCH.sub.3 OCH.sub.3 OCH.sub.372 H H H H H H CH.sub.372 H H H H H H OCH.sub.372 H H H H CH.sub.3 CH.sub.3 CH.sub.372 H H H H CH.sub.3 CH.sub.3 OCH.sub.372 H H H H CH.sub.3 OCH.sub.3 OCH.sub.372 H H H H OCH.sub.3 OCH.sub.3 OCH.sub.373 H H H H H H CH.sub.373 H H H H H H OCH.sub.373 H H H H CH.sub.3 CH.sub.3 CH.sub.373 H H H H CH.sub.3 CH.sub.3 OCH.sub.373 H H H H CH.sub.3 OCH.sub.3 OCH.sub.373 H H H H OCH.sub.3 OCH.sub.3 OCH.sub.374 H H H H CH.sub.3 CH.sub.3 CH.sub.374 H H H H CH.sub.3 CH.sub.3 OCH.sub.332 H H H H H H Cl32 H H H H H H H35 H H H H H -- Cl35 H H H H H -- H__________________________________________________________________________
TABLE VI__________________________________________________________________________ ##STR95##A R R.sub.1 R.sub.2 R.sub.3 R.sub.5 R.sub.6 Y.sub.1 m.p. (.degree.C.)__________________________________________________________________________1 H H H H H H CH.sub.31 H H H H 4-CH.sub.3 H CH.sub.32 H H H H H H OCH.sub.32 H H H H 5-CH.sub.3 H CH.sub.33 H H H H 2-CH.sub.3 5-CH.sub.3 OCH.sub.33 H H H H H H OCH.sub.34 H H H H H H OCH.sub.35 H H H H H H OCH.sub.35 H 5-Cl H H H H OCH.sub.36 H H H H H H CH.sub.36 H H H H H H OCH.sub.37 H H H H 3-CH.sub.3 4-CH.sub.3 CH.sub.38 H 5-F H H H H OCH.sub.38 H 5-Br H H 4-CH.sub.3 H OCH.sub.39 H H H H H H CH.sub.310 H H H H H H OCH.sub.311 H H H H H H OCH.sub.312 H H H H 5-SCH.sub.3 -- CH.sub.312 H H H H 5-CH.sub.3 -- OCH.sub.312 H H H H H -- CH.sub.312 H H H H H -- OCH.sub.313 H H H H 3-CH.sub.3 -- OCH.sub.314 H H H H 3-CH.sub.3 -- CH.sub.315 H H H H H -- CH.sub.315 H H H H CH.sub.3 -- OCH.sub.316 H H H H H -- OCH.sub.317 H 5-F H H -- -- CH.sub.318 H H H H CH.sub.3 -- CH.sub.319 H H H H CH.sub.3 CH.sub.3 CH.sub.319 H H H H CH.sub.3 CH.sub.3 OCH.sub.320 H H H H H H CH.sub.321 H 5-OCH.sub.3 H H H H OCH.sub.322 H 5-CF.sub.3 H H H H CH.sub.322 H 5-NO.sub.2 H H H -- OCH.sub.323 H H H H H -- OCH.sub.324 H H H H 5-CH.sub.3 -- CH.sub.325 H H H H H -- CH.sub.325 H H H H CH.sub.3 -- OCH.sub.326 H H H H H -- CH.sub.327 H 5-NO.sub.2 H H H -- OCH.sub.328 H H H H H -- OCH.sub.329 H H H H H -- CH.sub.329 H H H H H -- OCH.sub.330 H H H H H -- CH.sub.331 H 5-Cl H H H -- CH.sub.331 H H H H H -- CH.sub.331 H H H H H -- OCH.sub.332 H H H H H H CH.sub.332 H H H H H H OCH.sub.332 H H H H 4-CH.sub.3 H OCH.sub.333 H H H H H -- CH.sub.333 H H H H H -- OCH.sub.333 H H H H 2-CH.sub.3 -- OCH.sub.334 H H H H 2-CH.sub.3 -- OCH.sub.334 H H H H H -- OCH.sub.334 H H H H H -- CH.sub.335 H H H H H -- CH.sub.335 H H H H 5-CH.sub.3 -- OCH.sub.335 H H H H H -- OCH.sub.335 CH.sub.3 H H H H -- OCH.sub.335 H H CH.sub.3 H H -- OCH.sub.335 H H H CH.sub.3 H -- OCH.sub.336 H H H H H -- CH.sub.336 H H H H H -- OCH.sub.337 H H H H H -- CH.sub.337 H H H H H -- OCH.sub.338 H H H H H -- OCH.sub.338 H H H H CH.sub.3 -- OCH.sub.339 H H H H H -- CH.sub.339 H H H H H -- OCH.sub.340 H H H H H -- CH.sub.340 H H H H H -- OCH.sub.341 H H H H 4-Cl -- CH.sub.341 H H H H 4-CN -- CH.sub.341 H H H H H -- CH.sub.341 H H H H H -- OCH.sub.342 H H H H 4-Cl -- OCH.sub.342 H H H H 5-CH.sub.3 -- OCH.sub.342 H H H H H -- CH.sub.342 H H H H H -- OCH.sub.343 H H H H H H CH.sub.343 H H H H H H OCH.sub.343 H H H H 4-CH.sub.3 6-CH.sub.3 OCH.sub.343 H H H H 3-Cl 5-CH.sub.3 OCH.sub.343 H H H H 3-CH.sub.3 5-CH.sub.3 OCH.sub.343 H H H H 4-N(CH.sub.3).sub.2 H OCH.sub.343 H H H H 5-CN H OCH.sub.344 H H H H H H CH.sub.344 H H H H H H OCH.sub.345 H H H H H H CH.sub.345 H H H H H H OCH.sub.346 H H H H H H CH.sub.346 H H H H H H OCH.sub.346 H H H H 5-CH.sub.3 H OCH.sub.346 H H H H 5-CH.sub.3 6-CH.sub.3 OCH.sub.347 H H H H H H CH.sub.347 H H H H H H OCH.sub.347 H H H H 6-CH.sub.3 H OCH.sub.347 H H H H 3-CH.sub.3 6-CH.sub.3 OCH.sub.348 H H H H 5-CH.sub.3 H OCH.sub.348 H H H H 5-Cl H OCH.sub.348 H H H H H H CH.sub.348 H H H H H H OCH.sub.349 H H H H H H CH.sub.349 H H H H H H OCH.sub.349 H H H H 4-CH.sub.3 6-CH.sub.3 CH.sub.349 H H H H 4-CH.sub.3 6-CH.sub.3 OCH.sub.349 H H H H 4-OCH.sub.3 6-OCH.sub.3 CH.sub.349 H H H H 4-OCH.sub.3 6-OCH.sub.3 OCH.sub.349 H H H H 4-Cl 6-Cl OCH.sub.349 H H H H 4-Cl 4-N(CH.sub.3).sub.2 OCH.sub.349 H H H H 4-OCH.sub.3 6-SCH.sub.3 OCH.sub.349 H H H H 4-Cl 6-CN OCH.sub.350 H H H H H H CH.sub.350 H H H H H H OCH.sub.350 H H H H 2-CH.sub.3 6-CH.sub.3 OCH.sub.350 H H H H 2-CH.sub.3 6-OCH.sub.3 OCH.sub.350 H H H H 2-CH.sub.3 6-Cl OCH.sub.351 H H H H H H CH.sub.351 H H H H H H OCH.sub.351 H H H H 2-CH.sub.3 H OCH.sub.351 H H H H 5-CH.sub.3 H OCH.sub.351 H H H H OCH.sub.3 H OCH.sub.352 H H H H H H CH.sub.352 H H H H H H OCH.sub.352 H H H H CH.sub.3 CH.sub.3 OCH.sub.352 H H H H CH.sub.3 OCH.sub.3 OCH.sub.352 H H H H OCH.sub.3 OCH.sub.3 OCH.sub.353 H H H H H H CH.sub.353 H H H H H H OCH.sub.353 H H H H 5-CH.sub.3 6-CH.sub.3 OCH.sub.354 H H H H H H CH.sub.354 H H H H H H OCH.sub.355 H H H H H H CH.sub.355 H H H H H H OCH.sub.356 H H H H H -- CH.sub.356 H H H H H -- OCH.sub.356 H H H H 6-CH.sub.3 -- OCH.sub.357 H H H H H -- OCH.sub.357 H H H H 4-CH.sub.3 -- OCH.sub.358 H H H H H -- OCH.sub.358 H H H H 4-CH.sub.3 -- OCH.sub.359 H H H H H -- CH.sub.359 H H H H H -- OCH.sub.359 H H H H 4-CH.sub.3 -- OCH.sub.359 H H H H 5-CH.sub.3 -- OCH.sub.360 H H H H 4-CH.sub.3 -- OCH.sub.361 H H H H H -- OCH.sub.361 H H H H 5-CH.sub.3 -- OCH.sub.362 H H H H H -- CH.sub.362 H H H H H -- OCH.sub.363 H H H H H -- CH.sub.363 H H H H H -- OCH.sub.364 H H H H H -- CH.sub.364 H H H H H -- OCH.sub.365 H H H H H -- OCH.sub.366 H H H H H -- OCH.sub.367 H H H H H -- CH.sub.367 H H H H H -- OCH.sub.368 H H H H H -- CH.sub.368 H H H H H -- OCH.sub.369 H H H H H -- CH.sub.369 H H H H H -- OCH.sub.370 H H H H H -- CH.sub.370 H H H H H -- OCH.sub.371 H H H H H H CH.sub.371 H H H H H H OCH.sub.371 H H H H CH.sub.3 CH.sub.3 CH.sub.371 H H H H CH.sub.3 CH.sub.3 OCH.sub.371 H H H H CH.sub.3 OCH.sub.3 OCH.sub.371 H H H H OCH.sub.3 OCH.sub.3 OCH.sub.372 H H H H H H CH.sub.372 H H H H H H OCH.sub.372 H H H H CH.sub.3 CH.sub.3 CH.sub.372 H H H H CH.sub.3 CH.sub.3 OCH.sub.372 H H H H CH.sub.3 OCH.sub.3 OCH.sub.372 H H H H OCH.sub.3 OCH.sub.3 OCH.sub.373 H H H H H H CH.sub.373 H H H H H H OCH.sub.373 H H H H CH.sub.3 CH.sub.3 CH.sub.373 H H H H CH.sub.3 CH.sub.3 OCH.sub.373 H H H H CH.sub.3 OCH.sub.3 OCH.sub.373 H H H H OCH.sub.3 OCH.sub.3 OCH.sub.374 H H H H CH.sub.3 CH.sub.3 CH.sub.374 H H H H CH.sub.3 CH.sub.3 OCH.sub.332 H H H H H H Cl32 H H H H H H H35 H H H H H -- Cl35 H H H H H -- H__________________________________________________________________________
TABLE VII__________________________________________________________________________ ##STR96##A R R.sub.1 R.sub.2 R.sub.3 R.sub.5 R.sub.6 Y.sub.1 m.p. (.degree.C.)__________________________________________________________________________1 H H H H H H CH.sub.31 H H H H 4-CH.sub.3 H CH.sub.32 H H H H H H OCH.sub.32 H H H H 5-CH.sub.3 H CH.sub.33 H H H H 2-CH.sub.3 5-CH.sub.3 OCH.sub.33 H H H H H H OCH.sub.34 H H H H H H OCH.sub.35 H H H H H H OCH.sub.35 H 5-Cl H H H H OCH.sub. 36 H H H H H H CH.sub.36 H H H H H H OCH.sub.37 H H H H 3-CH.sub.3 4-CH.sub.3 CH.sub.38 H 5-F H H H H OCH.sub.38 H 5-Br H H 4-CH.sub.3 H OCH.sub.39 H H H H H H CH.sub.310 H H H H H H OCH.sub.311 H H H H H H OCH.sub.312 H H H H 5-SCH.sub.3 -- CH.sub.312 H H H H 5-CH.sub.3 -- OCH.sub.312 H H H H H -- CH.sub.312 H H H H H -- OCH.sub.313 H H H H 3-CH.sub.3 -- OCH.sub.314 H H H H 3-CH.sub.3 -- CH.sub.315 H H H H H -- CH.sub.315 H H H H CH.sub.3 -- OCH.sub.316 H H H H H -- OCH.sub.317 H 5-F H H -- -- CH.sub.318 H H H H CH.sub.3 -- CH.sub.319 H H H H CH.sub.3 CH.sub.3 CH.sub.319 H H H H CH.sub.3 CH.sub.3 OCH.sub.320 H H H H H H CH.sub.321 H 5-OCH.sub.3 H H H H OCH.sub.322 H 5-CF.sub.3 H H H H CH.sub.322 H 5-NO.sub.2 H H H -- OCH.sub.323 H H H H H -- OCH.sub.324 H H H H 5-CH.sub.3 -- CH.sub.325 H H H H H -- CH.sub.325 H H H H CH.sub.3 -- OCH.sub.326 H H H H H -- CH.sub.327 H 5-NO.sub.2 H H H -- OCH.sub.328 H H H H H -- OCH.sub.329 H H H H H -- CH.sub.329 H H H H H -- OCH.sub.330 H H H H H -- CH.sub.331 H 5-Cl H H H -- CH.sub.331 H H H H H -- CH.sub.331 H H H H H -- OCH.sub.332 H H H H H H CH.sub.332 H H H H H H OCH.sub.332 H H H H 4-CH.sub.3 H OCH.sub.333 H H H H H -- CH.sub.333 H H H H H -- OCH.sub.333 H H H H 2-CH.sub.3 -- OCH.sub.334 H H H H 2-CH.sub.3 -- OCH.sub.334 H H H H H -- OCH.sub.334 H H H H H -- CH.sub.335 H H H H H -- CH.sub.335 H H H H 5-CH.sub.3 -- OCH.sub.335 H H H H H -- OCH.sub.335 CH.sub.3 H H H H -- OCH.sub.335 H H CH.sub.3 H H -- OCH.sub.335 H H H CH.sub.3 H -- OCH.sub.336 H H H H H -- CH.sub.336 H H H H H -- OCH.sub.337 H H H H H -- CH.sub.337 H H H H H -- OCH.sub.338 H H H H H -- OCH.sub.338 H H H H CH.sub.3 -- OCH.sub.339 H H H H H -- CH.sub.339 H H H H H -- OCH.sub.340 H H H H H -- CH.sub.340 H H H H H -- OCH.sub.341 H H H H 4-Cl -- CH.sub.341 H H H H 4-CN -- CH.sub.341 H H H H H -- CH.sub.341 H H H H H -- OCH.sub.342 H H H H 4-Cl -- OCH.sub.342 H H H H 5-CH.sub.3 -- OCH.sub.342 H H H H H -- CH.sub.342 H H H H H -- OCH.sub.343 H H H H H H CH.sub.343 H H H H H H OCH.sub.343 H H H H 4-CH.sub.3 6-CH.sub.3 OCH.sub.343 H H H H 3-Cl 5-CH.sub.3 OCH.sub.343 H H H H 3-CH.sub.3 5-CH.sub.3 OCH.sub.343 H H H H 4-N(CH.sub.3).sub.2 H OCH.sub.343 H H H H 5-CN H OCH.sub.344 H H H H H H CH.sub.344 H H H H H H OCH.sub.345 H H H H H H CH.sub.345 H H H H H H OCH.sub.346 H H H H H H CH.sub.346 H H H H H H OCH.sub.346 H H H H 5-CH.sub.3 H OCH.sub.346 H H H H 5-CH.sub.3 6-CH.sub.3 OCH.sub.347 H H H H H H CH.sub.347 H H H H H H OCH.sub.347 H H H H 6-CH.sub.3 H OCH.sub.347 H H H H 3-CH.sub.3 6-CH.sub.3 OCH.sub.348 H H H H 5-CH.sub.3 H OCH.sub.348 H H H H 5-Cl H OCH.sub.348 H H H H H H CH.sub.348 H H H H H H OCH.sub.349 H H H H H H CH.sub.349 H H H H H H OCH.sub.349 H H H H 4-CH.sub.3 6-CH.sub.3 CH.sub.349 H H H H 4-CH.sub.3 6-CH.sub.3 OCH.sub.349 H H H H 4-OCH.sub.3 6-OCH.sub.3 CH.sub.349 H H H H 4-OCH.sub.3 6-OCH.sub.3 OCH.sub.349 H H H H 4-Cl 6-Cl OCH.sub.349 H H H H 4-Cl 4-N(CH.sub.3).sub.2 OCH.sub.349 H H H H 4-OCH.sub.3 6-SCH.sub.3 OCH.sub.349 H H H H 4-Cl 6-CN OCH.sub.350 H H H H H H CH.sub.350 H H H H H H OCH.sub.350 H H H H 2-CH.sub.3 6-CH.sub.3 OCH.sub.350 H H H H 2-CH.sub.3 6-OCH.sub.3 OCH.sub.350 H H H H 2-CH.sub.3 6-Cl OCH.sub.351 H H H H H H CH.sub.351 H H H H H H OCH.sub.351 H H H H 2-CH.sub.3 H OCH.sub.351 H H H H 5-CH.sub.3 H OCH.sub.351 H H H H OCH.sub.3 H OCH.sub.352 H H H H H H CH.sub.352 H H H H H H OCH.sub.352 H H H H CH.sub.3 CH.sub.3 OCH.sub.352 H H H H CH.sub.3 OCH.sub.3 OCH.sub.352 H H H H OCH.sub.3 OCH.sub.3 OCH.sub.353 H H H H H H CH.sub.353 H H H H H H OCH.sub.353 H H H H 5-CH.sub.3 6-CH.sub.3 OCH.sub.354 H H H H H H CH.sub.354 H H H H H H OCH.sub.355 H H H H H H CH.sub.355 H H H H H H OCH.sub.356 H H H H H -- CH.sub.356 H H H H H -- OCH.sub.356 H H H H 6-CH.sub.3 -- OCH.sub.357 H H H H H -- OCH.sub.357 H H H H 4-CH.sub.3 -- OCH.sub.358 H H H H H -- OCH.sub.358 H H H H 4-CH.sub.3 -- OCH.sub.359 H H H H H -- CH.sub.359 H H H H H -- OCH.sub.359 H H H H 4-CH.sub.3 -- OCH.sub.359 H H H H 5-CH.sub.3 -- OCH.sub.360 H H H H 4-CH.sub.3 -- OCH.sub.361 H H H H H -- OCH.sub.361 H H H H 5-CH.sub.3 -- OCH.sub.362 H H H H H -- CH.sub.362 H H H H H -- OCH.sub.363 H H H H H -- CH.sub.363 H H H H H -- OCH.sub.364 H H H H H -- CH.sub.364 H H H H H -- OCH.sub.365 H H H H H -- OCH.sub.366 H H H H H -- OCH.sub.367 H H H H H -- CH.sub.367 H H H H H -- OCH.sub.368 H H H H H -- CH.sub.368 H H H H H -- OCH.sub.369 H H H H H -- CH.sub.369 H H H H H -- OCH.sub.370 H H H H H -- CH.sub.370 H H H H H -- OCH.sub.371 H H H H H H CH.sub.371 H H H H H H OCH.sub.371 H H H H CH.sub.3 CH.sub.3 CH.sub.371 H H H H CH.sub.3 CH.sub.3 OCH.sub.371 H H H H CH.sub.3 OCH.sub.3 OCH.sub.371 H H H H OCH.sub.3 OCH.sub.3 OCH.sub.372 H H H H H H CH.sub.372 H H H H H H OCH.sub.372 H H H H CH.sub.3 CH.sub.3 CH.sub.372 H H H H CH.sub.3 CH.sub.3 OCH.sub.372 H H H H CH.sub.3 OCH.sub.3 OCH.sub.372 H H H H OCH.sub.3 OCH.sub.3 OCH.sub.373 H H H H H H CH.sub.373 H H H H H H OCH.sub.373 H H H H CH.sub.3 CH.sub.3 CH.sub.373 H H H H CH.sub.3 CH.sub.3 OCH.sub.373 H H H H CH.sub.3 OCH.sub.3 OCH.sub.373 H H H H OCH.sub.3 OCH.sub.3 OCH.sub.374 H H H H CH.sub.3 CH.sub.3 CH.sub.374 H H H H CH.sub.3 CH.sub.3 OCH.sub.332 H H H H H H Cl32 H H H H H H H35 H H H H H -- Cl35 H H H H H -- H__________________________________________________________________________
Formulations
Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
TABLE VIII______________________________________ Active Weight Percent* Ingredient Diluent(s) Surfactant(s)______________________________________Wettable Powders 20-90 0-74 1-10Oil Suspensions, 3-50 40-95 0-15Emulsions, Solutions,(including EmulsifiableConcentrates)Aqueous Suspension 10-50 40-84 1-20Dusts 1-25 70-99 0-5Granules and Pellets 0.1-95 5-99.9 0-15High Strength 90-99 0-10 0-2Compositions______________________________________ * Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.
Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0.degree. C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.
The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.
For further information regarding the art of formulation, see for example:
H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;
R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;
H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;
G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., New York, 1961, pp. 81-96; and
J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
In the following examples, all parts are by weight unless otherwise indicated.
EXAMPLE 6
Wettable Powder
______________________________________2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]- 80%aminsulfonyl]-N--(4,6-dimethylpyrimidin-2-yl)-benzamidesodium alkylnaphthalenesulfonate 2%sodium ligninsulfonate 2%synthetic amorphous silica 3%kaolinite 13%______________________________________
The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.
EXAMPLE 7
Wettable Powder
______________________________________2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]- 50%aminosulfonyl]-N--(thiazol-2-yl)benzamidesodium alkylnaphthalenesulfonate 2%low viscosity methyl cellulose 2%diatomaceous earth 46%______________________________________
The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.
EXAMPLE 8
Granule
______________________________________Wettable Powder of Example 7 5%attapulgite granules 95%(U.S.S. 20-40 mesh; 0.84-0.42 mm)______________________________________
A slurry of wettable powder containing .apprxeq.25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
EXAMPLE 9
Extruded Pellet
______________________________________2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]- 25%aminosulfonyl]-N--(2-pyridinyl)benzamideanhydrous sodium sulfate 10%crude calcium ligninsulfonate 5%sodium alkylnaphthalenesulfonate 1%calcium/magnesium bentonite 59%______________________________________
The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.
EXAMPLE 10
Oil Suspension
______________________________________2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocar- 25%bonyl]aminosulfonyl]-N--(1,3,4-thiadiazol-2-yl)-benzamidepolyoxyethylene sorbitol hexaoleate 5%highly aliphatic hydrocarbon oil 70%______________________________________
The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.
EXAMPLE 11
Wettable Powder
______________________________________N--(3,4-dimethylisoxazol-5-yl)-2-[[(4-methoxy-6-methyl- 20%pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-benzamidesodium alkylnaphthalenesulfonate 4%sodium ligninsulfonate 4%low viscosity methyl cellulose 3%attapulgite 69%______________________________________
The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
EXAMPLE 12
Low Strength Granule
______________________________________2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino- 1%carbonyl]aminosulfonyl]-N--(1-methyl-1H--pyrazol-3-yl)benzamideN,N--dimethylformamide 9%attapulgite granules 90%(U.S.S. 20-40 sieve)______________________________________
The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
EXAMPLE 13
Aqueous Suspension
______________________________________N--(3,4-dimethylisoxazol-5-yl)-2-[[(4-methoxy-6-methyl- 40%pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-benzamidepolyacrylic acid thickener 0.3%dodecylphenol polyethylene glycol ether 0.5%disodium phosphate 1%monosodium phosphate 0.5%polyvinyl alcohol 1.0%water 56.7%______________________________________
The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.
EXAMPLE 14
Solution
______________________________________2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]- 5%aminosulfonyl]-N--(1,2,4-triazol-3-yl)-benzamide, sodium saltwater 95%______________________________________
The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.
EXAMPLE 15
Low Strength Granule
______________________________________2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]- 0.1%aminosulfonyl]-N--(thiazol-2-yl)benzamide 99.9%attapulgite granules(U.S.S. 20-40 mesh)______________________________________
The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.
EXAMPLE 16
Granule
______________________________________2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino- 80%carbonyl]aminosulfonyl]-N--1-methyl-1H--pyrazol-3-yl)benzamidewetting agent 1%crude ligninsulfonate salt (containing 10%5-20% of the natural sugars)attapulgite clay 9%______________________________________
The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.
EXAMPLE 17
High Strength Concentrate
______________________________________2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]- 99%aminosulfonyl]-N--(1,2,4-triazol-3-yl)-benzamidesilica aerogel 0.5%synthetic amorphous silica 0.5%______________________________________
The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.
EXAMPLE 18
Wettable Powder
______________________________________2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]- 90%aminosulfonyl]-N--(2-pyridinyl)benzamidedioctyl sodium sulfosuccinate 0.1%synthetic fine silica 9.9%______________________________________
The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.
EXAMPLE 19
Wettable Powder
______________________________________2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocar- 40%bonyl]aminosulfonyl]-N--(1,3,4-thiadiazol-2-yl)-benzamidesodium ligninsulfonate 20%montmorillonite clay 40%______________________________________
The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.
EXAMPLE 20
Oil Suspension
______________________________________2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]- 35%aminosulfonyl]-N--(4,6-dimethylpyrimidin-2-yl)-benzamideblend of polyalcohol carboxylic 6%esters and oil soluble petroleumsulfonatesxylene 59%______________________________________
The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.
Utility
The compounds of the present invention are powerful herbicides. They have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds are useful for the selective control of weeds in crops such as wheat and alfalfa.
The rates of application for the compounds of the invention are determined by a number of factors, including their use as selective or general herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.125 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, or for situations where only short-term persistence is required.
The compounds of the invention may be used in combination with any other commercial herbicide examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types.
The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.
Test A
Seeds of crabgrass (Digitaria sp. ), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory (Ipomoea sp.), cocklebur (Xanthium sp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers (Cyperus rotundus) were planted in a growth medium and treated pre-emergence with the chemicals dissolved in a non-phytotoxic solvent. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the third trifoliolate leaf expanding, crabgrass, barnyardgrass and wild oats with two leaves, cassia with three leaves (including cotyledonary ones), morningglory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with four leaves, soybean with two cotyledonary leaves, rice with three leaves, wheat with one leaf, and nutsedge with three to five leaves were sprayed. Treated plants and controls were maintained in a greenhouse for sixteen days, whereupon all species were compared to controls and visually rated for response to treatment.
The ratings are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:
C=chlorosis/necrosis;
D=defoliation;
E=emergence inhibition;
G=growth retardation;
H=formative effects;
I=increased chlorophyl;
S=albinism;
U=unusual pigmentation;
X=axillary stimulation; and
6Y=abscised buds or flowers.
The ratings for the compounds tested by this procedure are presented in Table A.
Some of the compounds included in this table, e.g. compounds 1, 3, 4 and 6, were relatively inactive at the very low rates of applications selected, i.e. 0.05 kg/ha. It can reasonably be expected that they would have performed better at higher treatment levels.
TABLE A______________________________________Structures ##STR97## Compound 1 ##STR98## Compound 2 ##STR99## Compound 3 ##STR100## Compound 4 ##STR101## Compound 5 ##STR102## Compound 6 ##STR103## Compound 7 ##STR104## Compound 8 ##STR105## Compound 9 ##STR106## Compound 10 ##STR107## Compound 11 ##STR108## Compound 12 ##STR109## Compound 13 ##STR110## Compound 14 ##STR111## Compound 15 ##STR112## Compound 16 ##STR113## Compound 17 ##STR114## Compound 18 ##STR115## Compound 19 ##STR116## Compound 20 ##STR117## Compound 21 ##STR118## Compound 22 ##STR119## Compound 23 Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POST-EMERGENCEBush bean 2G 4C,9G,6Y 0 0Cotton 1H 2C,6G 0 2HMorningglory 2H 4C,7G 3G 1HCocklebur 1H 3C,6G 0 1HCassia 0 2C 0 0Nutsedge 0 0 0 0Crabgrass 0 0 0 0Barnyardgrass 0 5G 0 0Wild Oats 0 0 0 0Wheat 0 0 0 0Corn 0 0 0 0Soybean 2C,5G 1H,2C,6G 1H 0Rice 0 2C 0 0Sorghum 0 2C 0 0PRE-EMERGENCEMorningglory 0 3C,5H 0 1CCocklebur 0 2C 0 0Cassia 0 2C 0 0Nutsedge 0 0 0 0Crabgrass 0 2G 0 0Barnyardgrass 0 1C 0 0Wild Oats 0 3G 0 0Wheat 0 2G 0 0Corn 0 2C 0 1CSoybean 0 2C 0 0Rice 0 2C 0 0Sorghum 0 2C,5G 0 0______________________________________ Cmpd. 5 Cmpd. 6 Cmpd. 7 Cmpd. 8Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POST-EMERGENCEBush bean 6C,9G,6Y 0 9C 9CCotton 4C,9G 0 5C,9G 4C,9GMorningglory 2C,8G 0 2C,5G 2C,9HCocklebur 2H,4G 0 2C,9G 1C,9HCassia 2C,5G 0 5C,9G 5C,9GNutsedge 1C,9G 0 9G 2C,9GCrabgrass 1C,5G 0 2C,9G 2C,8GBarnyardgrass 9H 0 5C,9G 5C,9HWild Oats 6G,5X 0 9G 2C,9GWheat 6G 0 2C,9G 1C,9GCorn 3U,9H 0 5U,9G 2U,9HSoybean 4C,9G 0 9C 9CRice 4C,9G 0 5C,9G 5C,9GSorghum 2C,9G 0 3C,9G 2C,9GPRE-EMERGENCEMorningglory 8G 0 9G 9HCocklebur 9H 0 9G 9HCassia 5G 0 7G 8GNutsedge 10E 0 10E 9GCrabgrass 3C 0 5G 5GBarnyardgrass 2C,9H 0 2C,9H 3C,9HWild Oats 2C,7G 0 2C,8G 2C,8GWheat 1C,8G 0 9H 1C,9GCorn 3C,8G 0 3C,9G 3C,9GSoybean 1C,5H 0 7H 2C,7HRice 9H 0 10E 10ESorghum 1C,8G 0 5C,9H 2U,9G______________________________________ Cmpd. 9 Cmpd. 10 Cmpd. 11 Cmpd. 12Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POST-EMERGENCEBush bean 0 6C,9G,6Y 5C,9G,6Y 4S,8G, 6YCotton 0 5C,9G 1U,4C,9G 2C,7GMorningglory 0 5C,9G 1C,3G 1C,6GCocklebur 0 1H 2C,8G 0Cassia 0 2C 1C,5G 2CNutsedge 4G 1C 5C,9G 0Crabgrass 1C,5G 0 2C,8G 0Barnyardgrass 1C,5G 0 6C,9H 0Wild Oats 0 0 1C,8G 0Wheat 0 0 5C,9G 0Corn 1C,4G 2C,6H 5U,9G 0Soybean 1H 2C,7G 3C,9G 1C,1HRice 1C,5G 0 9C 0Sorghum 1C,9G 1C,8H 9C 0PRE-EMERGENCEMoringglory 0 9G 9G 4GCocklebur 9H 9H 9H 5HCassia 1C 1C 1C,5G 0Nutsedge 2G 0 8G 0Crabgrass 0 0 1C,5G 0Barnyardgrass 2G 1C 1C,9H 0Wild Oats 2G 0 1C,8G 0Wheat 2G 0 9G 0Corn 1C,6G 1C,6G 1U,9G 1CSoybean 0 1C,2H 2C,6H 1HRice 1C,3G 1C,3G 9H 0Sorghum 1C,5H 1C,5G 1C,9G 0______________________________________ Cmpd. 13 Cmpd. 14 Cmpd. 15Rate kg/ha 0.05 0.4 0.05______________________________________POST-EMERGENCEBush bean 9C 8D,9G,6Y 9CCotton 4C,9G 9G 2U,3C, 9GMorningglory 2C,5G -- 10CCocklebur 4C,9G 4G 2C,8GCassia 6G 9G 6C,9GNutsedge 9G 9G 2C,4GCrabgrass 2C,8G 5G 2CBarnyardgrass 3C,9H -- 2CWild Oats 2C,9G -- 1CWheat 2C,9G 9G 1CCorn 5U,9G 9C 3C,9HSoybean 6C,9G 9G 9CRice 6C,9G 9G 2C,7GSorghum 2U,9G 9C 3C,8HPRE-EMERGENCEMorningglory 9G 9G 9GCocklebur 9H -- 9HCassia 6G 9G 3C,9GNutsedge 10E 10E 10ECrabgrass 2C,8G 2C,8G 3GBarnyardgrass 2C,9H 3C,9G 2C,4GWild Oats 1C,9G 1C,8G 1CWheat 9G 1C,9G 0Corn 2C,9G 1U,9G 2C,6GSoybean 6H 9H 2C,4HRice 10E 10E 2C,5HSorghum 5C,9H 9H 2C,7G______________________________________ Cmpd. 16 Cmpd. 17 Cmpd. 18 Cmpd. 19Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POST-EMERGENCEBush bean 5C,9G,6Y 9C 10D,9G 9D,9G, 6YCotton 3C,9G 4C,8G 2U,5C,9G 2C,3H, 9GMorningglory 5G 2C,8G 2C 1C,4GCocklebur 6G 4G 5C,9G 2GCassia 4G 2G 5C,8G 2C,4GNutsedge 2C,9G 8G 9G 7GCrabgrass 1C,9G 5G 1C,9G 5GBarnyardgrass 2C,9H 3C,9H 2C,9H 5C,9HWild Oats 9G 1C,5G 1C,9H 5GWheat 9G 1C,5G 9G 6GCorn 1C,9G 2C,9H 3U,9G 2C,9HSoybean 2C,7H 2C,9G 5C,9G 2C,8GRice 9G,5I 2C,9G 4C,9G 1C,9GSorghum 9G,5I 1C,9G 5U,9G 9GPRE-EMERGENCEMorningglory 9G 9G 9G 9GCocklebur 9H 9H 9H 9HCassia 7G 8G 8G 8GNutsedge 10E 10E 10E 9GCrabgrass 3C,7G 1C,5G 1C,5G 2C,4GBarnyardgrass 2C,9G 5C,9H 3C,9H 9CWild Oats 9G 1C,9G 2C,9G 2C,9GWheat 9G 9G 9G 1C,9GCorn 3C,9G 2C,9G 9G 1C,9GSoybean 7H 8H 9H 1C,5GRice 10E 10E 10E 10ESorghum 5C,9H 2U,9G 6C,9H 2U,9G______________________________________ Cmpd. 20 Cmpd. 21 Cmpd. 22 Cmpd. 23Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POST-EMERGENCEBush bean 9C 6C,9G 9C 7C,9GCotton 2U,5C,9G 6C,9G 6C,9G 4C,9GMorningglory 2C,8G 2C 9C 3C,5GCocklebur 2G 4C,9G 5C,9G 1C,4GCassia 4C,6G 1C,3G 5C,9G 2CNutsedge 0 5C,9G 8G 2C,8GCrabgrass 0 3C,9G 2C,8G 2C,8GBarnyardgrass 0 9C 10C 3C,9HWild Oats 0 9G 9G 4C,9GWheat 0 4C,9G 5C,6G 2C,8GCorn 1C,5H 5U,9G 5U,9C 2C,9HSoybean 2C,9G 6C,9G 9C 6C,9GRice 4G 2C,9G 5C,9G 2C,9GSorghum 2C,9G 5C,9G 9C 2C,9GPRE-EMERGENCEMorningglory 9G 9G 9G 9GCocklebur 7H 9H 9H 8HCassia 7G 8G 9G 7GNutsedge 0 10E 10E 10ECrabgrass 1C 1C,7G 2C,8G 5G,1CBarnyardgrass 1C 4C,9H 5C,9H 2C,9GWild Oats 0 2C,8G 2C,9H 2C,8GWheat 0 1C,9H 2C,9H 2C,9GCorn 1C,4G 10E 9G 8GSoybean 1C,3G 5H 9H 2C,6HRice 2C,4G 10E 10E 4C,9HSorghum 2C 5C,9H 5C,9H 9G______________________________________
Test B
Two plastic bulb pans were filled with fertilized and limed Fallsington silt loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grassy weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grassy and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense), dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugarbeets. The above four containers were treated pre-emergence with several test compounds within the scope of the invention.
Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system described previously for Test A. The data are summarized in Table B. Note that certain compounds have relative tolerance for wheat.
TABLE B__________________________________________________________________________PRE-EMERGENCE ONFALLSINGTON SILT LOAM__________________________________________________________________________ Compound 5 Compound 7 Compound 8 Compound 11 Compound 13 Compound Compound 17Rate kg/ha .060 .250 .030 .120 .030 .120 .060 .250 .030 .120 0.25 0.0625 0.250.0625__________________________________________________________________________Crabgrass 0 0 0 4G,2H 0 4G 0 6G 0 3G 8G,3H 7G,3H 6G,3H 5G,2HBarnyardgrass 4C,6G 5C,7G 5G,3H 7G,5H 6G,2H 8G,6C 7G,5H 9G,9C 3G 5G 8G,9C 8G,8C 8G,8C7G,5CSorghum 7G,5H 8G,5H 8G,5H 10C 6G,3H 8G 8G,8C 10C 5G,3H 9G,9C 10E 10C 9C,9G7G,5HWild Oats 5G 6G,3H 5G 7G 5G 7G 7G,3H 7G,6C 4G 6G,3H 6G,3C 6G,3H 6G,3H 5GJohnsongrass 3G 7G,3H 7G,5H 7G,5H 4G,3H 7G,5H 6G,3H 7G,5H 4G 7G,5H 8G,5H 5H,7G 7G,5H 3H,4GDallisgrass 0 4G 2G 5G 0 4G 6G 8G,3H 2G 6G 7C,8G 8G,3H 6G5GGiant foxtail 0 7G,5H 2G 5G,3H 4G,3H 7G,3H 7G,5H 9G,5H 0 3G,2H 8G,9C 7G,5C 7G,6C6G,3CKy. bluegrass 5G,3H 6G,3H 6G,3H 6G,3H 5G 6G,3H 7G,7C 8G,8C 6G 7G 8G,8C 8G,7C 8G,8C7GCheatgrass 8G,8C 10C 7G 7G 6G 7G,5E 8G,9C 10E 8G 8G 10C 10C 7G,8C10CSugarbeets 7G,8C 9G,9C 8G,8C 9G,9C 8G,7C 9G,9C 7G,8C 9G,9C 6G,4C 8G,8C 8G,9C 8G,8C 8G,8C8G,8CCorn 0 8G,5H 7G,5H 10C 3G 6G,3H 3H 7G,5H 3G 3G 9G,9C 9G,9C 5G,5H 3GMustard 10C 10C 8G,6C 9G,9C 8G,8C 9G,9C 9G,8C 10C 7G,6C 9G,9C 10C 8G,8C 9G,9C8G,8CCocklebur 5G 5G,3H 6G 7G,5H 3G 7G 3G 6G,3H 6G,5C 6G,2C 7G 5G 6G3GPigweed 6G,5C 8G,8C -- -- -- -- 9G,9C 10C -- -- 10C 10C 9G,9C10CNutsedge 9G 8G 10E 10E 0 10E 3G 10E 9G 10E 10E 8G 3G3GCotton 8G,5C 7G 8G,8C 9G,9C 0 8G,8C 2G 9G,8C 7G,3H 8G,5H 9G 7G 7G6GMorningglory 7G 8G 5G 7G 0 8G 5G 8G,5C 7G 8G 9G,5C 7G,3C 9G,8C5GCassia 8G,3C 7G,3C 5G 5G 0 7G 4G,3C 7G,3C 5G 7G,5C 6G 3G 7G5GTeaweed 4G 4G 0 5C,7G 0 7G,3C 4G 6G 4G 7G,4C 6G,3C 3G 5G0Velvetleaf 6G,3H 7G,6C 8G,5H 9G,9C 6G,5H 10C 8G,5H 8G,7C 6G,3H 7G,5H 9G,5H 8G,5H 6G,3H 5G,3HJimsonweed 4G,4C 7G,6C 0 5G,3C 0 5G,5C 5G,3C 7G,5C 0 3G,3C 6G,3C 4G 6G,4C3G,4CSoybean 4G,3H 6G,3H 4G 7G,5H 4G 8G,8C 3G,2C 9G,8C 3G,3H 5G,3H 7G,5H 4G,1C 5H,7G 5G,2HRice 7G,5H 10C 10E 10E 7G 10E 8G,8C 10C 9G,9C 10C 10E 10E 7G,5H 7G,5HWheat 4G 5G 4G 7G,3H 3G 6G,3H 4G 7G,5C 3G 4G 7G,3C 6G,2C 5G4G__________________________________________________________________________ Compound 18 Compound 19 Compound 20 Compound 21 Compound 22 Compound Compound 14Rate kg/ha 0.12 0.0312 0.12 0.0312 0.12 0.0312 0.12 0.0312 0.12 0.0312 0.12 0.0312 0.250.06__________________________________________________________________________Crabgrass 6G 5G 3G 0 0 0 7G 4G 5G 3G 0 0 3H0Barnyardgrass 8G,8C 8G,3C 7G,5C 5G,2C 0 0 8G 5G 8G,3H 6G,2H 5G 0 5G,3H 0Sorghum 10C 9G,9C 7G,3H 6G,3H 3G 0 10C 7G,3H 9G,9C 9G,3H 7G,5H 2G 8G,5H 5G,5HWild Oats 6G,6C 6G,3C 6G,2H 4G 0 0 7G 4G 7G,3H 4G 4G 0 4G0Johnsongrass 8G,8C 8C,8G 7G,5H 4G,3H 0 0 7G 3G 8G 7G 3G 0 6G,3H 0Dallisgrass 3H,8G 7G,3H 4G 3G 0 0 5G 0 5G 2G 3G 0 00Giant foxtail 8G,5H 8G,5H 6G,3H 4G 0 0 5G,3H 0 8G,5H 4G 3G 0 00Ky. bluegrass 7G,8C 7G,8C 6G 5G 3G 0 6G 5G 6C,6G 5G 5G 0 8G,8C5G,5HCheatgrass 10E 10E 7G,8C 6G 0 0 9G,9C 7G 10E 5G 0 0 3G,3H 3GSugarbeets 9G,9C 7G,7C 8G,8C 6G,5C 8G,8C 8G,8C 7G,7C 6G,5H 8G,8C 6G,3H 7G,6C 4G 7G,8C6G,7CCorn 10E 10E 8C,8G 4G 2G 0 6G,5H 0 4G 0 0 0 3G,0Mustard 10C 8G,5C 9G,8C 5C,8G 7G,5C 5G 9G,9C 8G,8C 9G,9C 8G,8C 9G,9C 6G,5C 9G,9C6G,5ECocklebur 8G,5C 6G 6G 5G 6G 7G 5G,3H 5G 2G -- 3G 0 4G0Pigweed 10C 7G 7G,6C 3G 6G 0 -- -- -- -- -- -- 10C7G,9ENutsedge 10E 10E 7G 5G 3G 0 10E 2G 3G 0 7G 0 3G0Cotton 9G,5H 9G,5H 3H,6G 0 9G,3H 7G,3H 3H,7G 3G 5G,5H 4G,3H 3G 0 8G2GMorningglory 8G,5C 7G,3C 7G,5H 3G 8G,3H 5G 7G,3H 3H 3G 4G 3G 3G 8G4GCassia 5G 5G 4G 3G 5G 4G 7G,3C 3G 6G 6G 5G 0 8G0Teaweed 7G 5G 4G 3G 3G 2G 10E 3G 6G,3C 4G 2G 0 5G0Velvetleaf 9G,5C 8G,3H 6G,5H 4G,3H 2G 3G 7G,8C 5G,3H 5G,5H 4G,3H 5G,3H 0 6G0Jimsonweed 9G,8C 5G,3C 5G 2G 4G 3G 6G,3C 4G 4G,3C 3G 3G 0 7G,7C0Soybean 8G,5H 7G,5H 6G,5H 2H 5G,1C 2G 5G,3H 2G 3G 4G 2G 0 00Rice 10E 10E 7G 5G 0 0 10E 10E 10E 7G 7G,7C 3G 8G,3H 6GWheat 7G 7G,3C 4G 2G 0 0 4G 0 3G 3G 2G 0 360__________________________________________________________________________
Test C
Twenty-five cm diameter plastic pots filled with Fallsington silt loam were planted with soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia (Cassia tora), morningglory (Ipomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthium pensylvanicum), crabgrass (Digitaria sp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). Approximately 21/2 weeks after planting, the young plants and the soil around them were sprayed overall with the test chemicals dissolved in a non-phytotoxic solvent. Two weeks after treatment, all species were compared to untreated controls and visually rated for response to treatment. The rating system was as described previously for Test A. The data are presented in Table C. Note that one compound is especially tolerant to alfalfa.
TABLE C POST-EMERGENCE Over-the-Top Soil/Foliage Treatment Compound 5 Compound 7 Compound 8 Compound 11 Compound 13 Compound 15 Compound 16 Compound 17 Rate kg/ha 0.06 0.0125 0.06 0.0125 0.06 0.125 0.06 0.125 0.006 0.06 0.125 0.06 0.125 0.006 .063 .016 .250 .063 Soybeans 10G,7C 8G,5C 10G,8C 10G,3C 9G,6C 10G,5C 10C 8G,5C 2C 9G,2C 5G 10G,7C 10G,3C 6G 8G 8G 9G 6G Velvetleaf 9G,8C 6G 10C 9G 10C 7G 10C 10C 0 9G,4C 2G,2C 9G,8C 5G,2C 6G 9G,7C 8G,4C 9G,9C 7G,5C Sesbania 9G,3C 7G 9G,3C 8G 10C 8G 10C 10C 4G 8G 2G 9G,9C 5G 7G 8G 7G,5C 9G,8C 7G,2C Cassia 9G,3C 3G 8G 4G 8G 5C 9G,9C 9G,9C 2C 2C 0 9G,8C 9G,6C 0 2C 3G,2C 9G,7C 9G,7C Cotton 8G 6G 10G 7G 10G 9G,5C 9G,9C 9G,9C 2C 8G 2G 10G 8G,3C 6G 6G 2G 8G,3C 7G,2C Morningglory 9G 3G 9G,6C 8G 9G,9C 8G 9G,9C 9G,9C 2G 9G 4G 9G,5C 7G 7G 2G 0 9G,7C 8G,7C Alfalfa 9G,5C 2G 6G 9G 10C 8G 10C 10C 4G 3G 0 10C 9G 6G 2C 2C 10C 8G,7C Jimsonweed 0 0 9G 0 10C 7G 9G,4C 9G,2C 5G 0 2C 10C 4G 2G 5G 5G 7G 8G Cocklebur 0 0 8G 5G 8G 5G 9G 6G 0 5G 2C 8G 2G 4G 8G 7G 8G 8G Sunflower 4G 0 8G,2H 6G 8G 5G 9G,9C 7G 2C 4G 4G 10C 6G,2H 3G 5G 7G 8G,6C 4G,4C Mustard 9G 9G 9G,9C 9G 10C 9G 10C 10C 0 9G 7G 10C 8G 4G 10C 10C 9G,9C 9G,9C Sugarbeets 8G 5G,3C 8G 9G 10C 9G,8C 10C 9G,4C 3G 9G 4G 9G,9C 5G 6G 9G 9G 9G,5C 9G,5C Corn 8G,3U 8G,3U 9G,9U 9G,9C 10C 7G,3U 9G,9C 9C,3C 4G 8G,3U 8G,1H 7G,3U 6G 2G 9G,5C 9G,5C 10C 9G,9C Crabgrass 0 4C 4G 0 0 0 2G 0 0 2G 0 0 0 3G 10C 7G 6G,3C 2G Rice 4G,2C 4G 7G,3C 7G,3C 6G,5C 4G 10C 9G,8C 0 8G 8G 0 0 0 7G,4C 7G,1C 9G,8C 7G Nutsedge 8G 9C 7G 9C 10C 3G,3C 9G,9C 9G,9C 0 8G,7C 7G 0 0 3G 6G 4G 10C 9C Barnyardgrass 7G 5G 9G,9C 8G,8C 10C 8G 9G,8C 9G,2U 3G 9G,2H 6G 0 0 2G 9G,4C 10C 9G,8C 8G Wheat 0 0 9G,2C 5G 5G,2C 3G 7G,5U 6G,4C 0 7G,3C 5G 0 0 0 8G,2C 8G,4C 9G,4C 9G,2C Giant foxtail 0 0 8G 4G 9G 5G 9G,2U 8G 2G 6G 0 0 6G 0 8G 8G 8G,3C 8G Wild Oats 4G,4C 2C 9G,9C 7G 6G,2C 2G 10C 7G,2C 0 7G,3C 6G,2C 0 0 0 9G 8G,5C 9G,4C 8G Sorghum 7G 6G 8G,8C 7G,2U 7G 6G 10C 8G,6C 4G 7G 7G 4G 0 2G 10C 8G,8C 8G,9C 8G,8C Johnsongrass 5G 5G 9G,8C 9G,2U 10C 9G,3U -- -- 5G 9G,2U 4G 0 3G 3G 9G,7U 8G,7U 9G,8C 7G,3U Field Bindweed 5G 4G 7G 0 10C 6G -- -- 2C 0 2G 10C 8G 0 5G -- 5G 2G Compound 17 Compound 18 Compound 21 Compound 22 Compound 23 Rate kg/ha . 016 0.06 0.0125 0.006 0.006 0.06 0.0125 0.06 0.0125 0.006 0.006 0.06 0.0125 Soybeans 6G 10G,6C 8G 9G 5G 10C 10G,5C 10C 10C 10G,3C 10G,5C 10G,6C 8G,6C Velvetleaf 7G 9G 8G 5G 4G 9G,8C 6G 10C 8G,5C 7G,2C 10C 6G 2G Sesbania 7G 9G 2G 4G 8G 9G,8C 6G 10C 10C 9G,8C 10G,6C 9G,5C 3G Cassia 6G 9G 5G,3C 0 0 8G 2G 8G 9G,8C 5G,3C 4G 8G,2C 7G Cotton 4G 9G,5C 2G 1C 5G 9G 3G 9G,5C 8G,2C 8G,2C 7G 9G,5C 7G Morningglory 8G,5C 3G 4G 0 4G 9G 0 9G,8C 9G,7C 8G,2C 8G 5G 4G Alfalfa 6G,3C 2G,2C 0 4G 0 9G,5C 0 9G,9C 7G,5C 8G,2C 6G 8G,6C 5G Jimsonweed 2G 9G 6G 8G,2C 0 7G 0 9G 9G 4G 3G 0 0 Cocklebur 4G 7G 6G 0 6G 8G 5G 8G 6G 4G 6G 3G 0 Sunflower 6G,2C 8G,2H 4G 0 2C 8G,1H 3G 8G 5G 5G 10C 6G 1G Mustard 7G,2C 9G,5C 8G 5G 2G 10C 8G 10C 7G 8G 7G,3C 6G 8G Sugarbeets 8G 9G,5C 8G 5G 6G 10C 9G 10C 10C 1G 9G 5G 0 Corn 9G,7C 8G,8C 8G,3C 8G,5H 6G,3H 10C 9G,7C 10C 10C 7G,8C 7G,3H 9G,5C 9G,3U Crabgrass 0 4G 0 0 0 7G 0 4G,2C 3G 0 4G 0 0 Rice 7G 9G,5C 7G 3G,2C 4G 10C 7G,7C 10C 8G,8C 5G,5C 7G 7G,3C 2G Nutsedge 2G 10C 10C 8G,2C 4G 7G,7C 5G,5C 10C 10C 7C 0 8G 3C Barnyardgrass 4G 9G,6C 10C 4G,2C 1G 10C 10C 10C 10C 6G,2C 7G,1H 10C 5G Wheat 2G 9G 6G 5G 1G 9G,8C 5G 8G,6C 8G,2C 2G 2G 1G 0 Giant foxtail 7G 8G 4G 0 4G 9G 8G 9G,2C 9G 2G 3G 4G 4G Wild Oats 4G 9G,5C 5G 0 0 8G 6G 9G,8C 9G 2G 0 6G 1C Sorghum 7G 10C 7G,8C 6G 8G 10C 7G,3C 10C 8G,3C 8G 7G 8G,5C 6G Johnsongrass 4G 9G,8C 10C 5G,4U 5G 9G,8U 7G,3U 10C 10C 6G,4C 7G,2H 9G,2U 7G Field Bindweed 0 5G 0 0 0 10C 2G 6G 9G 7G 3G 2G 2C

Herbicidal sulfonamides

Information

Patent Number

Date Filed

Date Issued

Inventors

Original Assignees

Examiners

CPC

US Classifications

Field of Search

US

International Classifications

Abstract

Description

Claims

Parent Case Info

US Referenced Citations (1)

Foreign Referenced Citations (1)

Divisions (1)

Continuation in Parts (1)