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## 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: ##STR2## 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: ##STR3## 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, clover and Poa annua.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR4## 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: ##STR5## wherein R is butyl, phenyl or ##STR6## 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: ##STR7## 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)]: ##STR8## wherein R=H or CH.sub.3.
Unexamined European Pat. No. 7687 discloses, among others, herbicidal sulfonylureas of the general structure: ##STR9## 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 ##STR10## where R is H, C.sub.1 -C.sub.12 alkyl, --(CH.sub.2 CH.sub.2 O)--.sub.n'" R.sub.12, CH.sub.2 CH.sub.2 CH.sub.2 OR.sub.12, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.5 -C.sub.8 cycloalkyl substituted with 1-3 substituents selected from 0-2 OCH.sub.3, 0-3 CH.sub.3 or C.sub.2 H.sub.5, trifluoromethylcyclohexyl, C.sub.4 -C.sub.10 cycloalkylalkyl, C.sub.4 -C.sub.8 cycloalkylalkyl substituted with 1-2 CH.sub.3, CH.sub.2 CH.sub.2 CN, C(CH.sub.3).sub.2 CN, OCH.sub.3, OC.sub.2 H.sub.5, N(CH.sub.3).sub.2, ##STR11## R.sub.6 is H, C.sub.1 -C.sub.3 alkyl, allyl, CH.sub.2 CN or CH.sub.2 CH.sub.2 CN; or
R.sub.6 and R may be taken together as --(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 --, --CH.sub.2 CH.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 -- or ##STR12## provided that when R is OCH.sub.3 or OC.sub.2 H.sub.5, then R.sub.6 is H or CH.sub.3 ; when R.sub.6 is CH.sub.2 CH.sub.2 CN or CH.sub.2 CN, then R is CH.sub.2 CH.sub.2 CN or CH.sub.2 CN; R and R.sub.6 have a total number of carbon atoms .gtoreq.13 and that when NR.sub.6 R is other than NHOCH.sub.3, NHOC.sub.2 H.sub.5 or ##STR13## then R.sub.2 is NCO, NHC(O)B, NHC(O)SB.sup.I, NHC(O)OB.sup.II, NHC(O)NHB.sup.III, CF.sub.3 SO.sub.2 NH or CH.sub.3 SO.sub.2 NH.
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. ##STR14## 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 ##STR15## 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 ##STR16## 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;
2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(2-pyridinyl)benzamide;
2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminocarbonyl]-N-(1,2,4-triazol-3-yl)benzamide;
2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1-methyl-1H-pyrazol-3-yl)benzamide;
2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(thiazol-2-yl)benzamide;
2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1,3,4-thiadiazol-2-yl)benzamide; and
N-(3,4-dimethylisoxazol-5-yl)-2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzamide.
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. ##STR17##
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 preparation 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 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 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)aminocarbonyl-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, 4.4 ppm 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______________________________________ ##STR18## 1 ##STR19## 2 ##STR20## 3 ##STR21## 4 ##STR22## 5 ##STR23## 6 ##STR24## 7 ##STR25## 8 ##STR26## 9 ##STR27## 10 ##STR28## 11 ##STR29## 12 ##STR30## 13 ##STR31## 14 ##STR32## 15 ##STR33## 16 ##STR34## 17 ##STR35## 18 ##STR36## 19 ##STR37## 20 ##STR38## 21 ##STR39## 22 ##STR40## 23 ##STR41## 24 ##STR42## 25 ##STR43## 26 ##STR44## 27 ##STR45## 28 ##STR46## 29 ##STR47## 30 ##STR48## 31 ##STR49## 32 ##STR50## 33 ##STR51## 34 ##STR52## 35 ##STR53## 36 ##STR54## 37 ##STR55## 38 ##STR56## 39 ##STR57## 40 ##STR58## 41 ##STR59## 42 ##STR60## 43 ##STR61## 44 ##STR62## 45 ##STR63## 46 ##STR64## 47 ##STR65## 48 ##STR66## 49 ##STR67## 50 ##STR68## 51 ##STR69## 52 ##STR70## 53 ##STR71## 54 ##STR72## 55 ##STR73## 56 ##STR74## 57 ##STR75## 58 ##STR76## 59 ##STR77## 60 ##STR78## 61 ##STR79## 62 ##STR80## 63 ##STR81## 64 ##STR82## 65 ##STR83## 66 ##STR84## 67 ##STR85## 68 ##STR86## 69 ##STR87## 70 ##STR88## 71 ##STR89## 72 ##STR90## 73 ##STR91## 74______________________________________
TABLE II__________________________________________________________________________ ##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.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.334 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__________________________________________________________________________ ##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 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 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__________________________________________________________________________ ##STR94##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__________________________________________________________________________ ##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 VI______________________________________ ##STR96## m.p.A R R.sub.1 R.sub.2 R.sub.3 R.sub.5 R.sub.6 Y.sub.1 (.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 VII______________________________________ ##STR97## m.p.A R R.sub.1 R.sub.2 R.sub.3 R.sub.5 R.sub.6 Y.sub.1 (.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.49 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-Comparisons______________________________________ *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%aminosulfonyl]-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 (0.42 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)benzamideattapulgite granules 99.9%(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-methylpyzimidin-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 broadspectrum 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 rates 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______________________________________ ##STR98## Compound 1 ##STR99## Compound 2 ##STR100## Compound 3 ##STR101## Compound 4 ##STR102## Compound 5 ##STR103## Compound 6 ##STR104## Compound 7 ##STR105## Compound 8 ##STR106## Compound 9 ##STR107## Compound 10 ##STR108## Compound 11 ##STR109## Compound 12 ##STR110## Compound 13 ##STR111## Compound 14 ##STR112## Compound 15 ##STR113## Compound 16 ##STR114## Compound 17 ##STR115## Compound 18 ##STR116## Compound 19 ##STR117## Compound 20 ##STR118## Compound 21 ##STR119## Compound 22 ##STR120## Compound 23______________________________________
TABLE A__________________________________________________________________________ Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4 Cmpd. 5 Cmpd. 6 Cmpd. 7 Cmpd. Cmpd. 9Rate kg/ha 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05__________________________________________________________________________POST-EMERGENCEBush bean 2G 4C,9G,6Y 0 0 6C,9G,6Y 0 9C 9C 0Cotton 1H 2C,6G 0 2H 4C,9G 0 5C,9G 4C,9G 0Morningglory 2H 4C,7G 3G 1H 2C,8G 0 2C,5G 2C,9H 0Cocklebur 1H 3C,6G 0 1H 2H,4G 0 2C,9G 1C,9H 0Cassia 0 2C 0 0 2C,5G 0 5C,9G 5C,9G 0Nutsedge 0 0 0 0 1C,9G 0 9G 2C,9G 4GCrabgrass 0 0 0 0 1C,5G 0 2C,9G 2C,8G 1C,5GBarnyardgrass 0 5G 0 0 9H 0 5C,9G 5C,9H 1C,5GWild Oats 0 0 0 0 6G,5X 0 9G 2C,9G 0Wheat 0 0 0 0 6G 0 2C,9G 1C,9G 0Corn 0 0 0 0 3U,9H 0 5U,9G 2U,9H 1C,4GSoybean 2C,5G 1H,2C,6G 1H 0 4C,9G 0 9C 9C 1HRice 0 2C 0 0 4C,9G 0 5C,9G 5C,9G 1C,5GSorghum 0 2C 0 0 2C,9G 0 3C,9G 2C,9G 1C,9G__________________________________________________________________________ Cmpd. 10 Cmpd. 11 Cmpd. 12 Cmpd. 13 Cmpd. 14 Cmpd. 15 Cmpd. 16 Cmpd. Cmpd. 18Rate kg/ha 0.05 0.05 0.05 0.05 0.4 0.05 0.05 0.05 0.05__________________________________________________________________________POST-EMERGENCEBush bean 6C,9G,6Y 5C,9G,6Y 4S,8G,6Y 9C 8D,9G,6Y 9C 5C,9G,6Y 9C 10D,9GCotton 5C,9G 1U,4C,9G 2C,7G 4C,9G 9G 2U,3C,9G 3C,9G 4C,8G 2U,5C,9GMorningglory 5C,9G 1C,3G 1C,6G 2C,5G -- 10C 5G 2C,8G 2CCocklebur 1H 2C,8G 0 4C,9G 4G 2C,8G 6G 4G 5C,9GCassia 2C 1C,5G 2C 6G 9G 6C,9G 4G 2G 5C,8GNutsedge 1C 5C,9G 0 9G 9G 2C,4G 2C,9G 8G 9GCrabgrass 0 2C,8G 0 2C,8G 5G 2C 1C,9G 5G 1C,9GBarnyardgrass 0 6C,9H 0 3C,9H -- 2C 2C,9H 3C,9H 2C,9HWild Oats 0 1C,8G 0 2C,9G -- 1C 9G 1C,5G 1C,9HWheat 0 5C,9G 0 2C,9G 9G 1C 9G 1C,5G 9GCorn 2C,6H 5U,9G 0 5U,9G 9C 3C,9H 1C,9G 2C,9H 3U,9GSoybean 2C,7G 3C,9G 1C,1H 6C,9G 9G 9C 2C,7H 2C,9G 5C,9GRice 0 9C 0 6C,9G 9G 2C,7G 9G,5I 2C,9G 4C,9GSorghum 1C,8H 9C 0 2U,9G 9C 3C,8H 9G,5I 1C,9G 5U,9G__________________________________________________________________________ Cmpd. 19 Cmpd. 20 Cmpd. 21 Cmpd. Cmpd. 23 Rate kg/ha 0.05 0.05 0.05 0.05 0.05__________________________________________________________________________ POST-EMERGENCE Bush bean 9D,9C,6Y 9C 6C,9G 9C 7C,9G Cotton 2C,3H,9G 2U,5C,9G 6C,9G 6C,9G 4C,9G Morningglory 1C,4G 2C,8G 2C 9C 3C,5G Cocklebur 2G 2G 4C,9G 5C,9G 1C,4G Cassia 2C,4G 4C,6G 1C,3G 5C,9G 2C Nutsedge 7G 0 5C,9G 8G 2C,8G Crabgrass 5G 0 3C,9G 2C,8G 2C,8G Barnyardgrass 5C,9H 0 9C 10C 3C,9H Wild Oats 5G 0 9G 9G 4C,9G Wheat 6G 0 4C,9G 5C,6G 2C,8G Corn 2C,9H 1C,5H 5U,9G 5U,9C 2C,9H Soybean 2C,8G 2C,9G 6C,9G 9C 6C,9G Rice 1C,9G 4G 2C,9G 5C,9G 2C,9G Sorghum 9G 2C,9G 5C,9G 9C 2C,9G__________________________________________________________________________ Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4 Cmpd. 5 Cmpd. 6 Cmpd. 7 Cmpd. Cmpd. 9Rate kg/ha 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05__________________________________________________________________________PRE-EMERGENCEMorningglory 0 3C,5H 0 1C 8G 0 9G 9H 0Cocklebur 0 2C 0 0 9H 0 9G 9H 9HCassia 0 2C 0 0 5G 0 7G 8G 1CNutsedge 0 0 0 0 10E 0 10E 9G 2GCrabgrass 0 2G 0 0 3C 0 5G 5G 0Barnyardgrass 0 1C 0 0 2C,9H 0 2C,9H 3C,9H 2GWild Oats 0 3G 0 0 2C,7G 0 2C,8G 2C,8G 2GWheat 0 2G 0 0 1C,8G 0 9H 1C,9G 2GCorn 0 2C 0 1C 3C,8G 0 3C,9G 3C,9G 1C,6GSoybean 0 2C 0 0 1C,5H 0 7H 2C,7H 0Rice 0 2C 0 0 9H 0 10E 10E 1C,3GSorghum 0 2C,5G 0 0 1C,8G 0 5C,9H 2U,9G 1C,5H__________________________________________________________________________ Cmpd. 10 Cmpd. 11 Cmpd. 12 Cmpd. 13 Cmpd. 14 Cmpd. 15 Cmpd. 16 Cmpd. Cmpd. 18Rate kg/ha 0.05 0.05 0.05 0.05 0.4 0.05 0.05 0.05 0.05__________________________________________________________________________PRE-EMERGENCEMorningglory 9G 9G 4G 9G 9G 9G 9G 9G 9GCocklebur 9H 9H 5H 9H -- 9H 9H 9H 9HCassia 1C 1C,5G 0 6G 9G 3C,9G 7G 8G 8GNutsedge 0 8G 0 10E 10E 10E 10E 10E 10ECrabgrass 0 1C,5G 0 2C,8G 2C,8G 3G 3C,7G 1C,5G 1C,5GBarnyardgrass 1C 1C,9H 0 2C,9H 3C,9G 2C,4G 2C,9G 5C,9H 3C,9HWild Oats 0 1C,8G 0 1C,9G 1C,8G 1C 9G 1C,9G 2C,9GWheat 0 9G 0 9G 1C,9G 0 9G 9G 9GCorn 1C,6G 1U,9G 1C 2C,9G 1U,9G 2C,6G 3C,9G 2C,9G 9GSoybean 1C,2H 2C,6H 1H 6H 9H 2C,4H 7H 8H 9HRice 1C,3G 9H 0 10E 10E 2C,5H 10E 10E 10ESorghum 1C,5G 1C,9G 0 5C,9H 9H 2C,7G 5C,9H 2U,9G 6C,9H__________________________________________________________________________ Cmpd. 19 Cmpd. 20 Cmpd. 21 Cmpd. Cmpd. 23 Rate kg/ha 0.05 0.05 0.05 0.05 0.05__________________________________________________________________________ PRE-EMERGENCE Morningglory 9G 9G 9G 9G 9G Cocklebur 9H 7H 9H 9H 8H Cassia 8G 7G 8G 9G 7G Nutsedge 9G 0 10E 10E 10E Crabgrass 2C,4G 1C 1C,7G 2C,8G 5G,1C Barnyardgrass 9C 1C 4C,9H 5C,9H 2C,9G Wild Oats 2C,9G 0 2C,8G 2C,9H 2C,8G Wheat 1C,9G 0 1C,9H 2C,9H 2C,9G Corn 1C,9G 1C,4G 10E 9G 8G Soybean 1C,5G 1C,3G 5H 9H 2C,6H Rice 10E 2C,4G 10E 10E 4C,9H Sorghum 2U,9G 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 grass 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 sugar beets. 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__________________________________________________________________________ Com- Compound 5 Compound 7 Compound 8 Compound 11 Compound 13 Compound pound 17Rate kg/ha .060 .250 .030 .120 .030 .120 .060 .250 .030 .120 0.25 0.0625 0.25__________________________________________________________________________Crabgrass 0 0 0 4G,2H 0 4G 0 6G 0 3G 8G,3H 7G,3H 6G,3HBarnyardgrass 4C,6G 5C,7G 5G,3H 7G,5H 6G,2H 8G,6C 7G,5H 9G,9C 3G 5G 8G,9C 8G,8C 8G,8CSorghum 7G,5H 8G,5H 8G,5H 10C 6G,3H 8G 8G,8C 10C 5G,3H 9G,9C 10E 10C 9C,9GWild Oats 5G 6G,3H 5G 7G 5G 7G 7G,3H 7G,6C 4G 6G,3H 6G,3C 6G,3H 6G,3HJohnsongrass 3G 7G,3H 7G,5H 7G,5H 4G,3H 7G,5H 6G,3H 7G,5H 4G 7G,5H 8G,5H 5H,7G 7G,5HDallisgrass 0 4G 2G 5G 0 4G 6G 8G,3H 2G 6G 7C,8G 8G,3H 6GGiant foxtail 0 7G,5H 2G 5G,3H 4G,3H 7G,3H 7G,5H 9G,5H 0 3G,2H 8G,9C 7G,5C 7G,6CKy. bluegrass 5G,3H 6G,3H 6G,3H 6G,3H 5G 6G,3H 7G,7C 8G,8C 6G 7G 8G,8C 8G,7C 8G,8CCheatgrass 8G,8C 10C 7G 7G 6G 7G,5E 8G,9C 10E 8G 8G 10C 10C 7G,8CSugar beets 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,8CCorn 0 8G,5H 7G,5H 10C 3G 6G,3H 3H 7G,5H 3G 3G 9G,9C 9G,9C 5G,5HMustard 10C 10C 8G,6C 9G,9C 8G,8C 9G,9C 9G,8C 10C 7G,6C 9G,9C 10C 8G,8C 9G,9CCocklebur 5G 5G,3H 6G 7G,5H 3G 7G 3G 6G,3H 6G,5C 6G,2C 7G 5G 6GPigweed 6G,5C 8G,8C -- -- -- -- 9G,9C 10C -- -- 10C 10C 9G,9CNutsedge 9G 8G 10E 10E 0 10E 3G 10E 9G 10E 10E 8G 3GCotton 8G,5C 7G 8G,8C 9G,9C 0 8G,8C 2G 9G,8C 7G,3H 8G,5H 9G 7G 7GMorningglory 7G 8G 5G 7G 0 8G 5G 8G,5C 7G 8G 9G,5C 7G,3C 9G,8CCassia 8G,3C 7G,3C 5G 5G 0 7G 4G,3C 7G,3C 5G 7G,5C 6G 3G 7GTeaweed 4G 4G 0 5C,7G 0 7G,3C 4G 6G 4G 7G,4C 6G,3C 3G 5GVelvetleaf 6G,3H 7G,6C 8G,5H 9G,9C 6G,5H 10C 8G,5H 8G,7C 6G,3H 7G,5H 9G,5H 8G,5H 6G,3HJimsonweed 4G,4C 7G,6C 0 5G,3C 0 5G,5C 5G,3C 7G,5C 0 3G,3C 6G,3C 4G 6G,4CSoybean 4G,3H 6G,3H 4G 7G,5H 4G 8G,8C 3G,2C 9G,8C 3G,3H 5G,3H 7G,5H 4G,1C 5H,7GRice 7G,5H 10C 10E 10E 7G 10E 8G,8C 10C 9G,9C 10C 10E 10E 7G,5HWheat 4G 5G 4G 7G,3H 3G 6G,3H 4G 7G,5C 3G 4G 7G,3C 6G,2C 5G__________________________________________________________________________ Com- pound 17 Compound 18 Compound 19 Compound 20 Compound 21 Compound 22Rate kg/ha 0.0625 0.12 0.0312 0.12 0.0312 0.12 0.0312 0.12 0.0312 0.12 0.0312__________________________________________________________________________Crabgrass 5G,2H 6G 5G 3G 0 0 0 7G 4G 5G 3GBarnyardgrass 7G,5C 8G,8C 8G,3C 7G,5C 5G,2C 0 0 8G 5G 8G,3H 6G,2HSorghum 7G,5H 10C 9G,9C 7G,3H 6G,3H 3G 0 10C 7G,3H 9G,9C 9G,3HWild Oats 5G 6G,6C 6G,3C 6G,2H 4G 0 0 7G 4G 7G,3H 4GJohnsongrass 3H,4G 8G,8C 8C,8G 7G,5H 4G,3H 0 0 7G 3G 8G 7GDallisgrass 5G 3H,8G 7G,3H 4G 3G 0 0 5G 0 5G 2GGiant foxtail 6G,3C 8G,5H 8G,5H 6G,3H 4G 0 0 5G,3H 0 8G,5H 4GKy. bluegrass 7G 7G,8C 7G,8C 6G 5G 3G 0 6G 5G 6C,6G 5GCheatgrass 10C 10E 10E 7G,8C 6G 0 0 9G,9C 7G 10E 5GSugar beets 8G,8C 9G,9C 7G,7C 8G,8C 6G,5C 8G,8C 8G,8C 7G,7C 6G,5H 8G,8C 6G,3HCorn 3G 10E 10E 8C,8G 4G 2G 0 6G,5H 0 4G 0Mustard 8G,8C 10C 8G,5C 9G,8C 5C,8G 7G,5C 5G 9G,9C 8G,8C 9G,9C 8G,8CCocklebur 3G 8G,5C 6G 6G 5G 6G 7G 5G,3H 5G 2G --Pigweed 10C 10C 7G 7G,6C 3G 6G 0 -- -- -- --Nutsedge 3G 10E 10E 7G 5G 3G 0 10E 2G 3G 0Cotton 6G 9G,5H 9G,5H 3H,6G 0 9G,3H 7G,3H 3H,7G 3G 5G,5H 4G,3HMorningglory 5G 8G,5C 7G,3C 7G,5H 3G 8G,3H 5G 7G,3H 3H 3G 4GCassia 5G 5G 5G 4G 3G 5G 4G 7G,3C 3G 6G 6GTeaweed 0 7G 5G 4G 3G 3G 2G 10E 3G 6G,3C 4GVelvetleaf 5G,3H 9G,5C 8G,3H 6G,5H 4G,3H 2G 3G 7G,8C 5G,3H 5G,5H 4G,3HJimsonweed 3G,4C 9G,8C 5G,3C 5G 2G 4G 3G 6G,3C 4G 4G,3C 3GSoybean 5G,2H 8G,5H 7G,5H 6G,5H 2H 5G,1C 2G 5G,3H 2G 3G 4GRice 7G,5H 10E 10E 7G 5G 0 0 10E 10E 10E 7GWheat 4G 7G 7G,3C 4G 2G 0 0 4G 0 3G 3G__________________________________________________________________________ Compound Compound 14 Rate kg/ha 0.12 0.0312 0.25 0.06__________________________________________________________________________ Crabgrass 0 0 3H 0 Barnyardgrass 5G 0 5G,3H 0 Sorghum 7G,5H 2G 8G,5H 5G,5H Wild Oats 4G 0 4G 0 Johnsongrass 3G 0 6G,3H 0 Dallisgrass 3G 0 0 0 Giant foxtail 3G 0 0 0 Ky. bluegrass 5G 0 8G,8C 5G,5H Cheatgrass 0 0 3G,3H 3G Sugar beets 7G,6C 4G 7G,8C 6G,7C Corn 0 0 3G 0 Mustard 9G,9C 6G,5C 9G,9C 6G,5E Cocklebur 3G 0 4G 0 Pigweed -- -- 10C 7G,9E Nutsedge 7G 0 3G 0 Cotton 3G 0 8G 2G Morningglory 3G 3G 8G 4G Cassia 5G 0 8G 0 Teaweed 2G 0 5G 0 Velvetleaf 5G,3H 0 6G 0 Jimsonweed 3G 0 7G,7C 0 Soybean 2G 0 0 0 Rice 7G,7C 3G 8G,3H 6G Wheat 2G 0 3G 0__________________________________________________________________________
Test C
Twenty-five cm diameter plastic pots filled with Fallsington slit 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-EMERGENCEOver-the-Top Soil/Foliage Treatment__________________________________________________________________________ Com- Compound 5 Compound 7 Compound 8 Compound 11 Compound pound 15Rate kg/ha 0.06 0.0125 0.06 0.0125 0.06 0.0125 0.06 0.0125 0.006 0.06 0.0125 0.06__________________________________________________________________________Soybeans 10G,7C 8G,5C 10G,8C 10G,3C 9G,6C 10G,5C 10C 8G,5C 2C 9G,2C 5G 10G,7CVelvetleaf 9G,8C 6G 10C 9G 10C 7G 10C 10C 0 9G,4C 2G,2C 9G,8CSesbania 9G,3C 7G 9G,3C 8G 10C 8G 10C 10C 4G 8G 2G 9G,9CCassia 9G,3C 3G 8G 4G 8G 5G 9G,9C 9G,9C 2C 2C 0 9G,8CCotton 8G 6G 10G 7G 10G 9G,5C 9G,9C 9G,9C 2C 8G 2G 10GMorningglory 9G 3G 9G,6C 8G 9G,9C 8G 9G,9C 9G,9C 2G 9G 4G 9G,5CAlfalfa 9G,5C 2G 6G 9G 10C 8G 10C 10C 4G 3G 0 10CJimsonweed 0 0 9G 0 10C 7G 9G,4C 9G,2C 5G 0 2C 10CCocklebur 0 0 8G 5G 8G 5G 9G 6G 0 5G 2C 8GSunflower 4G 0 8G,2H 6G 8G 5G 9G,9C 7G 2C 4G 4G 10CMustard 9G 9G 9G,9C 9G 10C 9G 10C 10C 0 9G 7G 10CSugar beets 8G 5G,3C 8G 9G 10C 9G,8C 10C 9G,4C 3G 9G 4G 9G,9CCorn 8G,3U 8G,3U 9G,9U 9G,9C 10C 7G,3U 9G,9C 9C,3C 4G 8G,3U 8G,1H 7G,3UCrabgrass 0 4C 4G 0 0 0 2G 0 0 2G 0 0Rice 4G,2C 4G 7G,3C 7G,3C 6G,5C 4G 10C 9G,8C 0 8G 8G 0Nutsedge 8G 9C 7G 9C 10C 3G,3C 9G,9C 9G,9C 0 8G,7C 7G 0Barnyardgrass 7G 5G 9G,9C 8G,8C 10C 8G 9G,8C 9G,2U 3G 9G,2H 6G 0Wheat 0 0 9G,2C 5G 5G,2C 3G 7G,5U 6G,4C 0 7G,3C 5G 0Giant foxtail 0 0 8G 4G 9G 5G 9G,2U 8G 2G 6G 0 0Wild Oats 4G,4C 2C 9G,9C 7G 6G,2C 2G 10C 7G,2C 0 7G,3C 6G,2C 0Sorghum 7G 6G 8G,8C 7G,2U 7G 6G 10C 8G,6C 4G 7G 7G 4GJohnsongrass 5G 5G 9G,8C 9G,2U 10C 9G,3U -- -- 5G 9G,2U 4G 0Field Bindweed 5G 4G 7G 0 10C 6G -- -- 2C 0 2G 10C__________________________________________________________________________ Compound 15 Compound 16 Compound 17 Compound 18 Compound 21 0.0125 0.006 .063 .016 .250 .063 .016 0.06 0.0125 0.006 0.006 0.06 0.0125__________________________________________________________________________Soybeans 10G,3C 6G 8G 8G 9G 6G 6G 10G,6C 8G 9G 5G 10C 10G,5CVelvetleaf 5G,2C 6G 9G,7C 8G,4C 9G,9C 7G,5C 7G 9G 8G 5G 4G 9G,8C 6GSesbania 5G 7G 8G 7G,5C 9G,8C 7G,2C 7G 9G 2G 4G 8G 9G,8C 6GCassia 9G,6C 0 2C 3G,2C 9G,7C 9G,7C 6G 9G 5G,3C 0 0 8G 2GCotton 8G,3C 6G 6G 2G 8G,3C 7G,2C 4G 9G,5C 2G 1C 5G 9G 3GMorningglory 7G 7G 2G 0 9G,7C 8G,7C 8G,5C 3G 4G 0 4G 9G 0Alfalfa 9G 6G 2C 2C 10C 8G,7C 6G,3C 2G,2C 0 4G 0 9G,5C 0Jimsonweed 4G 2G 5G 5G 7G 8G 2G 9G 6G 8G,2C 0 7G 0Cocklebur 2G 4G 8G 7G 8G 8G 4G 7G 6G 0 6G 8G 5GSunflower 6G,2H 3G 5G 7G 8G,6C 4G,4C 6G,2C 8G,2H 4G 0 2C 8G,1H 3GMustard 8G 4G 10C 10C 9G,9C 9G,9C 7G,2C 9G,5C 8G 5G 2G 10C 8GSugar beets 5G 6G 9G 9G 9G,5C 9G,5C 8G 9G,5C 8G 5G 6G 10C 9GCorn 6G 2G 9G,5C 9G,5C 10C 9G,9C 9G,7C 8G,8C 8G,3C 8G,5H 6G,3H 10C 9G,7CCrabgrass 0 3G 10C 7G 6G,3C 2G 0 4G 0 0 0 7G 0Rice 0 0 7G,4C 7G,1C 9G,8C 7G 7G 9G,5C 7G 3G,2C 4G 10C 7G,7CNutsedge 0 3G 6G 4G 10C 9C 2G 10C 10C 8G,2C 4G 7G,7C 5G,5CBarnyardgrass 0 2G 9G,4C 10C 9G,8C 8G 4G 9G,6C 10C 4G,2C 1G 10C 10CWheat 0 0 8G,2C 8G,4C 9G,4C 9G,2C 2G 9G 6G 5G 1G 9G,8C 5GGiant foxtail 6G 0 8G 8G 8G,3C 8G 7G 8G 4G 0 4G 9G 8GWild Oats 0 0 9G 8G,5C 9G,4C 8G 4G 9G,5C 5G 0 0 8G 6GSorghum 0 2G 10C 8G,8C 8G,9C 8G,8C 7G 10C 7G,8C 6G 8G 10C 7G,3CJohnsongrass 3G 3G 9G,7U 8G,7U 9G,8C 7G,3U 4G 9G,8C 10C 5G,4U 5G 9G,8U 7G,3UField Bindweed 8G 0 5G -- 5G 2G 0 5G 0 0 0 10C 2G__________________________________________________________________________ Compound 22 Compound 23 Rate kg/ha 0.06 0.0125 0.006 0.006 0.06 0.0125__________________________________________________________________________ Soybeans 10C 10C 10G,3C 10G,5C 10G,6C 8G,6C Velvetleaf 10C 8G,5C 7G,2C 10C 6G 2G Sesbania 10C 10C 9G,8C 10G,6C 9G,5C 3G Cassia 8G 9G,8C 5G,3C 4G 8G,2C 7G Cotton 9G,5C 8G,2C 8G,2C 7G 9G,5C 7G Morningglory 9G,8C 9G,7C 8G,2C 8G 5G 4G Alfalfa 9G,9C 7G,5C 8G,2C 6G 8G,6C 5G Jimsonweed 9G 9G 4G 3G 0 0 Cocklebur 8G 6G 4G 6G 3G 0 Sunflower 8G 5G 5G 10C 6G 1G Mustard 10C 7G 8G 7G,3C 6G 8G Sugar beets 10C 10C 1G 9G 5G 0 Corn 10C 10C 7G,8C 7G,3H 9G,5C 9G,3U Crabgrass 4G,2C 3G 0 4G 0 0 Rice 10C 8G,8C 5G,5C 7G 7G,3C 2G Nutsedge 10C 10C 7C 0 8G 3C Barnyardgrass 10C 10C 6G,2C 7G,1H 10C 5G Wheat 8G,6C 8G,2C 2G 2G 1G 0 Giant foxtail 9G,2C 9G 2G 3G 4G 4G Wild Oats 9G,8C 9G 2G 0 6G 1C Sorghum 10C 8G,3C 8G 7G 8G,5C 6G Johnsongrass 10C 10C 6G,4C 7G,2H 9G,2U 7G Field Bindweed 6G 9G 7G 3G 2G 2C__________________________________________________________________________

Herbicidal sulfonamides

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