Isothioureido isoindolediones and use as plant growth regulators

DESCRIPTION OF THE INVENTION
Growth regulating effects have been observed upon application of many chemical substances to plants. In general, very few of these substances can be used with benefit to the plants which are affected. In most instances the beneficial effects, if any, are minor and the major effects are so drastic that the compounds can only be used for the destruction of the plants. Examples of compounds with drastic effects which have become useful as herbicides are 2,4-D, EPTC and alachlor. Although a relatively small number of growth regulants has proved to be commercially useful, there are many uses for active compounds, among which are the following:
Increase or induce flowering (pineapple).
Increase blossom set, pod set, seed set, and/or fruit set (prevent abortion of flowers or withered blossoms).
Increase size of fruits, vegetables, seed, and/or tubers (grapes, soybeans, sugar beets, etc.)
Decrease size of fruits, vegetables, seed, and/or tubers (potatoes, and grapefruits).
Increase number of tillers (cereals).
Increase number of shoots from crown (alfalfa).
Increase branching (soybeans) or widen branches (apples).
We have now discovered a group of novel compounds which display a great variety of growth regulating effects, indicating utility for many purposes, including uses mentioned above.
Briefly, the novel class of growth regulant compounds has the general structural formula: ##STR2## In which R is cyano, C.sub.1 to C.sub.4 alkyl, C.sub.3 to C.sub.5 alkenyl or fluoroalkenyl, propynyl, phenylallyl or C.sub.1 to C.sub.3 alkyl to which is attached a phenyl, bromophenyl, chlorophenyl, methylphenyl, pyridyl, benzoyl, trimethylacetyl, phenoxy, chlorophenoxy, methylthio, fluorobenzoyl, N-phenylcarbamyl, N-ethylcarbamyl, N-trifluoromethylthiadiazolylcarbamyl, carboxy or carbethoxy substituent.
R.sup.1 is H, acetyl, C.sub.1 to C.sub.3 alkyl, alkenyl or alkynyl to which may be attached phenyl, halophenyl, carbethoxy, vinyloxy or phenoxy groups, or R and R.sup.1 together may be C.sub.2 to C.sub.4 alkylene,
Ar is phenyl or benzoyl,
R.sup.2 is C.sub.1 to C.sub.4 alkyl, alkoxy, alkylene, alkylamino or alkylthio; phenoxy, benzyloxy, carbalkoxy, acetyl, methylenedioxy, trifluoromethyl, nitro, halo or cyano and n may be zero or an integer from 1 to 4, with the provision that at least one position ortho to the point of attachment of a phenyl ring of the Ar structure must be unsubstituted,
R.sup.3 is lower alkyl or halo and n' may be zero or an integer from 1 to 4.
By virtue of their basic chemical characteristics, the novel compounds may also exist in the form of salts, by addition of a strong acid, such as HBr or HCl. In the salt form the compounds are more easily formulated in water-soluble and water-dispersible formulations.
By selection of the substituent R, the lipophilic properties of the novel compounds may be modified to obtain desirable improvements in ease of formulation, particularly as emulsifiable concentrates, and also improvements in activity on many plant spacies.
The nature of the substituent group R.sup.1 is important to the intensity of the growth regulator effect. For highest activity, small alkyl or alkenyl groups having one to three carbon atoms are preferred.
The nature of the R.sup.2 substituents is not as critical as the aforementioned groups. However, both activity and selectivity of action may be adjusted to some degree by selection of these groups. In general, C.sub.1 to C.sub.4 alkyl or alkoxy, halo or cyano substituents are preferred and Ar is preferably phenyl.
In general the substituents designated R.sup.3 do not enhance appreciably the activity of the growth regulators. However, by choice of type and position of the R.sup.3 substituents, chemical stability may be improved and the growth regulator effect may be prolonged. Prolonging the effect may in some instances eliminate the need for a second application, so that the compounds may be utilized more efficiently. Unless this is economically advantageous, however, compounds in which n'=0 are preferred.
SYNTHESIS OF THE GROWTH REGULANTS
The novel compounds of this invetion may be manufactured by means of the general method comprising reacting a compound of the formula: ##STR3## in a non-reactive polar organic solvent with a compound of the formula R--X in which X is a leaving group exemplified by a chlorine, bromine, iodine or sulfate substituent. Specific procedures which are suitable for synthesis of representative compounds are outlined in the following chart and exemplified below. ##STR4##

It will be understood that when it is desired that R and R.sup.1 shall be different, the alkylation at the sulfur and amino locations is conveniently done in separate reaction steps. The following specific procedures illustrate the general methods of synthesis.
SYNTHESIS OF METHYL HYDROGEN PHTHALATE
Methanol (300 ml) was added in a single portion to 148 g (1.00 mole) of phthalic anhydride and the resulting suspension was stirred and heated at reflux for 36 hours; solution occurred during heating. The solvent was removed and the product was recrystallized from a mixture of ethyl acetate and hexane to afford 114.6 g of the title compound (Lit.: Beilstein, 9,797--mp 82.5.degree., 84.degree.).
SYNTHESIS OF METHYL PHTHALOYL CHLORIDE
Methyl hydrogen phthalate (110.0 g., 0.611 mole) and thionyl chloride (77.4 g., 0.650 mole) were mixed in 200 ml of chloroform, keeping the temperature below 30.degree.. After stirring for two hours at room temperature, the system was heated at reflux for five hours. The solvent was evaporated at reduced pressure and the crude product (120.9 g) was used without further purification (Lit.: Beilstein, 9, 797--no constants).
SYNTHESIS OF 2-(2-carboxybenzoyl)-1-methyl-N-phenylhydrazinethiocarboxamide (I)
This compound was made by reacting phthalic anhydride with 1-methyl-N-phenylhydrazinethiocarboxamide according to conventional procedures, as follows:
The hydrazinethiocarboxamide was dissolved in about 75 ml of dimethylformamide and placed in a 3-necked round-bottomed flask equipped with magnetic stirrer, condenser, additional powder funnel and thermometer. The anhydride was added in portions at 20.degree.. The contents were stirred overnight at room temperature, then poured into ice water the following morning. The resulting solid was recrystallized in hexane and ethanol (m.p. 155.degree.-156.degree. C.)
Optionally ring substituted phthalic anhydrides and substituted 2-carbomethoxybenzoyl chlorides may be condensed with substituted 1-methylhydrazinethiocarboxamides to give desired intermediate compounds as in the following scheme: ##STR5##
These methods are illustrated in the following specific procedures. The identity of the product was confirmed in each instance by means of infrared and nuclear magnetic resonance spectra. All melting points are as determined, uncorrected (Degrees C.).
N-METHYL-N-(PHENYLTHIOCARBAMOYL)-2-AMINO-1H-ISOINDOLE-1,3-(2H)DIONE (II)
To an ice-cold solution of 8.25 g (0.025 mole) of 2-(2-carboxybenzoyl)-1-methyl-N-phenylhydrazinethiocarboxamide in 225 ml of 1,2-dimethoxyethane at .about.2.degree. C., a solution of 5.5 g (0.027 mole) of N,N'-dicyclohexylcarbodiimide was added dropwise below 5.degree. C. with stirring. The mixture was stirred in the ice bath and then left at room temperature overnight. The mixture was filtered to remove N,N'-dicyclohexylurea and the filtrate was evaporated below 40.degree. C., under vacuum, to give a yellow amorphous solid which was stirred in 100 ml of dry ether and warmed gently. The ether solution was allowed to stand for a few hours and filtered to give 4.6 g (59%) of whitish yellow crystals, m.p. 142.degree.-144.degree..
Recrystallization from ethyl acetate-hexane gave whitish crystals, m.p. 151.degree.-153.degree..
Mass spectrum: M.sup.+ 311.
N-METHYL-N-(PHENYLTHIOCARBAMOYL)-2-AMINO-4-METHYL-1H-ISOINDOLE-1,3-(2H)DIONE
To a solution of 6.8 g (0.037 mole) of 1-methyl-N-phenylhydrazinethiocarboxamide and 3.0 g of pyridine in 100 ml dry dimethoxyethane, 2-carbomethoxy-6-methylbenzoyl chloride (8.0 g, 0.037 mole) was added and the resulting mixture was stirred at room temperature for 60 hours. The solvent was distilled and the residue was taken up in ethyl acetate, filtered and dried on anhydrous magnesium sulfate. Removal of the solvent gave 10 g (83%) of the desired product, m.p. 110.degree.-115.degree. (dec.).
2-AMINO-1H-ISOINDOLE-1,3-(2H)DIONE
To an ice-cold suspension of 14.7 g (0.1 mole) of phthalimide in 100 ml of 95% ethyl alcohol at 5.degree. C., with stirring, 3.6 ml (0.11 mole) of 96.8% hydrazine was added dropwise. A slight exothermic reaction was observed and the mixture was allowed to stir at 5.degree. C. for two hours. The mixture was diluted with 200 ml of ice water, stirred, filtered, washed with water and dried to give 12.2 g (75%) of white powder, m.p. 199.degree.-202.degree..
Recrystallization from methanol-water gave white needles, m.p. 201.degree.-203.degree..
N-(PHENYLTHIOCARBAMOYL)-2-AMINO-1H-ISOINDOLE-1,3-(2H)DIONE (IV)
To a suspension of 8.2 g (0.05 mole) of 2-amino-1H-isoindole-1,3-(2H)dione in 50 ml of dry 2-propanol, 6 ml (0.05 mole) of phenyl isothiocyanate was added. The mixture was stirred and refluxed for 3 hours, allowed to cool to room temperature and poured into 300 ml of 50% ethyl alcohol. After stirring for one hour, the solid which formed was filtered, washed with water and dried to give 12.1 g (81%) of the desired product as a white powder, m.p. 180.degree.-181.degree.. To make compounds in which Ar is benzoyl, benzoyl isothiocyanates may be employed in procedures of the type described above.
(EXAMPLE 1) PREPARATION OF 2-(1,2-DIMETHYL-3-PHENYLISOTHIOUREIDO)-1H-ISOINDOLE-1,3-(2H)-DIONE (III)
Method A
To a slurry of 3.3 g (0.01 M) of 2-(2-carboxybenzoyl)-1-methyl-N-phenylhydrazinethiocarboxamide and 4.1 g (0.03 m) of potassium carbonate in 100 ml of acetone, was added 4.3 g (0.03 m) of methyl iodide. After stirring at room temperature for 16 hrs, 500 ml of ice water was added and the pH adjusted to 3 with dil HCl. An oil separated which crystallized with continued stirring, was collected and washed with water to give 1.2 g (37% yield) of product, m.p. 88.degree.-90.degree..
Method B
Six grams (0.019 m) of N-Methyl-N-(phenylthiocarbamoyl)-2-amino-1H-isoindole-1,3-2H-dione was dissolved in 2 ml of DMF and 5 ml of methyl iodide, then stirred at room temperature for 16 hours. To the solid mass was addd ethyl acetate and the crystals collected, washed with ethyl acetate and dried to give 7.3 g of hydroiodide salt, m.p. 145.degree.-148.degree. (dec).
The free base was obtained by suspending the salt in dil NH.sub.4 OH and extracting with CHCl.sub.3 which was washed with water, sat. NaCl and dried over anhydrous Na.sub.2 SO.sub.4. Removal of the CHCl.sub.3 at reduced pressure in a rotary evaporator gave a residual oil which was crystallized from ether-petroleum ether, wt. 4.6 g, m.p. 90.degree.-91.degree. (75%).
(EXAMPLE 2) PREPARATION OF 2-(2-METHYL-3-PHENYLISOTHIOUREIDO)-1H-isoindole-1,3-(2H)DIONE (V)
To 100 ml of dry acetone, 5.0 g (0.018 m) of N-(phenylthiocarbamoyl)-2-amino-1-H-isoindole-1,3-(2H)dione and 2.5 g (0.018 m) powdered anhydrous potassium carbonate was added. To this suspension 1.1 ml (0.018 m) of methyl iodide was added and the mixture was stirred overnight at room temperature. The mixture was poured into .about.300 ml of water, stirred, filtered, washed with water and dried to give 4.4 g (78%) of a yellow powder, m.p. 161.degree.-164.degree.. Mass spectrum: M+311.
(EXAMPLE 3) PREPARATION OF 2-(1-ALLYL-2-METHYL-3-PHENYLISOTHIOUREIDO)-1-H-ISOINDOLE-1,3-(2H)DIONE
To 50 ml of dry acetone, 4.0 g (0.013 m) of the product of Example 2, 2.2 g (0.016 m) of powdered anhydrous potassium carbonate, and 1.4 ml (0.016 m) of allyl bromide was added in succession and the mixture stirred overnight at room temperature. The mixture was poured into 300 ml of ice water with stirring. The aqueous layer was decanted and the residue suspended in fresh ice cold water, stirred and filtered to give a yellow semisolid product. This was purified by stirring in hexane to give a yellow powder 1.8 g (39%), m.p. 78.degree.-81.degree..
(EXAMPLE 4) PREPARATION OF 2-(1,2-DIALLYL-3-PHENYLISOTHIOUREIDO)-1-H-ISOINDOLE-1,3-(2H)DIONE
A mixture of 100 ml dry acetone, 5.0 g (0.018 m) N-(phenylthiocarbamoyl)-2-amino-1-H-isoindole-1,3-(2H)dione, 6.9 g (0.05 m) powdered anhydrous potassium carbonate, and 4.3 ml (0.05 m) allyl bromide was stirred overnight at room temperature and evaporated to dryness. The residue was suspended in 50 ml of cold water and the product was extracted with ether. The ether extract, on work-up, gave 4.7 g (69%) of thick yellow liquid.
USE OF THE GROWTH REGULATORS
The growth of plants may be regulated by applying the growth regulator compounds to the plants, either on seed, the soil or directly on the plants in an effective amount. If the objective is to combat unwanted vegetation, an amount sufficient to produce severe injury or abnormality of form of growth is usually sufficient. Sometimes the unwanted vegetation continues to live for a time but is stunted or distorted so that it cannot compete with crop plants and eventually succumbs to shading by the crop, or failure to obtain or to assimilate nutrients in the manner of a normal plant. An effect which is occasionally observed upon pre-emergent application is a loss of geotropic orientation upon germination of seed. In extreme cases roots may grow upward out of the soil, while leaves remain beneath the surface. Naturally the plants do not survive for long in this upside-down orientation. However, they can be transplanted and made to survive, which indicates that the growth regulant in one sense is not very phytotoxic. The survival rate of affected plants is much greater when the growth regulants are applied post-emergently, because the plants are already past the critical stages of emergence and growth of foliage and a root system. Retarded growth, with some abnormalities of form, accompanied by an increase in chlorophyl concentration in foliage is sometimes observed after post-emergent application. This combination of properties is particularly desirable for use on turf, to obtain a good color and reduce the frequency of cutting.
In highly active compounds, phytotoxic effects of pre-emergent and post-emergent application are often readily apparent. These effects may be demonstrated by means of the following illustrative procedures.
PRE-EMERGENT APPLICATION
Disposable paper trays about 21/2 inches deep were filled with soil and sprayed with aqueous spray mixtures at a rate of 5 lb. of active chemical per acre of sprayed area, were seeded with 6 species of plant seeds and were then covered with about 1/4 inch of soil. The spray mixtures were prepared by dissolving the proper amount of growth regulant compound in 15 ml of acetone, adding 4 ml of a solvent-emulsifier mixture consisting of 60 wt. percent of a commercial polyoxyethylated vegetable oil emulsifier (96 wt. percent active ingredient, Emulphor EL-719), 20 wt. percent xylene and 20 wt. percent deodorized kerosene, then bringing total volume up to 60 ml by addition of warm water. Twenty-one days after seeding and treatment the plantings were examined and plant injury was rated according to the following schedule.
DEGREE OF EFFECT
0=no effect
1=slight effect, plants recovered
2=moderate effect, injury to 26 to 75 percent
3=severe effect, injury to 76 to 99 percent of foliage
4=maximum effect (all plants died).
POST-EMERGENT APPLICATION
Several species of plants were grown in potting soil in disposable styrofoam trays and tomatoes were grown in four-inch pots in the greenhouse. Aqueous spray formulations were prepared and the growing plants were sprayed at a spray volume of 60 gallons per acre and an application rate of 5 lb. per acre. Spray mixtures were prepared in the manner described above. For comparative purposes, plants were also sprayed at 60 gal./acre with a spray mixture containing no growth regulator. Plant injury was again rated according to the schedule disclosed above and observations of growth regulant effects in both pre- and post-emergent tests were observed and recorded as follows:
______________________________________Effect Abbreviation in Tables______________________________________Formative effect on new growth FEpinasty EGrowth reduction GNecrosis NNon-emergence K______________________________________
In the table below there are tabulated various compounds which have been made according to the above illustrative procedures, as well as observations of pre-and post-emergent herbicidal and growth regulant effects. Some of the compounds were tested in the form of the hydrohalide salts, resulting from alkylation with alkyl halides. These compounds are identified under the column titled "salt type".
TABLE I__________________________________________________________________________EFFECTS ON PLANT SPECIESof Compounds of the formula ##STR6##Com-pound SaltNo. R R.sup.1 (R.sup.2)n (R.sup.3)n' Type M.P.__________________________________________________________________________ .degree.C.2878 CH.sub.3 CH.sub.3 n = 0 n' = 0 88-90.degree.-2960 6allyl CH.sub.3 n = 0 n' = 0 oil2961 benzyl CH.sub.3 n = 0 n' = 0 oil3062 CH.sub.3 H n = 0 n' = 0 161-4.degree.3099 CH.sub.3 CH.sub.3 3-F n' = 0 62-5.degree.3100 CH.sub.2 CH.sub.3 CH.sub.3 n = 0 n' = 0 80-2.degree.3101 allyl CH.sub.3 3-F n' = 0 oil3102 benzyl CH.sub.3 3-F n' = 0 oil3104 CH.sub.3 CH.sub.3 2,4-(CH.sub.3).sub.2 n' = 0 107-9.degree.3105 n-propyl CH.sub.3 n = 0 n' = 0 oil3110 4-Br CH.sub.3 n = 0 n' = 0 oil Benzyl3111 CH.sub.2 COC(CH.sub.3).sub.3 CH.sub.3 n = 0 n' = 0 HBr 135-8.degree.3129 CH.sub.3 CH.sub.3 2,6-(CH.sub. 3).sub.2 n' = 0 137-40.degree. 3,4-3130 CH.sub.3 CH.sub.3 CHCHCHCH n' = 0 wax3134 CH.sub.3 CH.sub.3 2,4,5-(CH.sub.3).sub.3 n' = 0 oil3135 CH.sub.3 CH.sub.3 2,5-(CH.sub.3).sub.2 n' = 0 122-4.degree.3141 CH.sub.3 CH.sub.3 n = 0 n' = 0 HI 145-8.degree. dec.3143 Allyl CH.sub.3 n = 0 n' = 0 HBr 117-8.degree.3144 benzyl CH.sub.3 n = 0 n' = 0 HBr 147-8.degree.3171 CH.sub.2CH.sub.2 n = 0 n' = 0 75-80.degree.3176 CH.sub.3 Allyl n = 0 n' = 0 78-81.degree.3191 CH.sub.3 CH.sub.32,3-(CH.sub.3).sub.2 n' = 0 95-7.degree.3192 CH.sub.3 CH.sub.3 4-phenoxy n' = 0 159-62.degree.3193 CH.sub.3 CH.sub.3 4-n-butyl n' = 0 oil3205 ##STR7## CH.sub.3 n = 0 n' = 0 HBr 166-8.degree.3206 " CH.sub.3 n = 0 n' = 0 67-70.degree.3215 CH.sub.3 CH.sub.2 CCH n = 0 n' = 0 oil3216 allyl allyl n = 0 n' = 0 oil3218 CH.sub.3 H 4-CH.sub.3 n' = 0 151-3.degree.3219 allyl H 4-CH.sub.3 n' = 0 128-30.degree.3220 CH.sub.3 CH.sub.3 4-CH.sub.3 n' = 0 111-114.degree.3221 CH.sub.3 allyl 4-CH.sub.3 n' = 0 oil3222 allyl H n = 0 n' = 0 60-61.degree.3251 3,3-dimethyl H n = 0 n' = 0 115-7.degree. allyl3274 CH.sub.3 ##STR8## n = 0 n' = 0 oil3276 CH.sub.3 H3-CH.sub.3 n' = 0 158-9.degree.3277 CH.sub.3 CH.sub.33-CH.sub.3 n' = 0 oil3278 allyl allyl3-CH.sub.3 n' = 0 oil3292 CH.sub.2 CCH CH.sub.33-F n' = 0 HBr 140-1.degree.3293 CH.sub.2 CCH CH.sub.33-F n' = 0 90-2.degree.3294 CH.sub.3 CH.sub.33-Cl n' = 0 oil3295 CH.sub.3 CH.sub.33,4-Cl.sub.2 n' = 0 124-7.degree.3296 CH.sub.3 H3-Cl n' = 0 198-200.degree.3297 CH.sub.3 H3,4-Cl.sub.2 n' = 0 182-3.degree.3298 CH.sub.3 allyl 3-Cl n' = 0 102-4.degree.__________________________________________________________________________EFFECTS ON PLANT SPECIESof Compounds of the formula ##STR9##Com-pound SaltNo. R R.sup.1 (R.sup. 2)n Type M.P. .degree.C.__________________________________________________________________________3283 allyl CH.sub.3 2,5-(CH.sub.3).sub.2 HBr 129-1303287 allyl CH.sub.3 2,5-(CH.sub.3).sub.2 Syrup3409 CH.sub.2 COOC.sub.2 H.sub.5 " 4-F HBr 169-1713410 CH.sub.2 COOC.sub.2 H.sub.5 " 4-F 83-853411 CH.sub.2 COOC.sub.2 H.sub.5 " 3-F HBr 138-1403497 C.sub.2 H.sub.5 H n = 0 130-1383500 C.sub.2 H.sub.5 allyl n = 0 Syrup3627 CH.sub.3 CH.sub.3 3-CF.sub.3 Oil3628 CH.sub.3 CH.sub.3 4-Cl 123-1253629 CH.sub.2 CH.sub.2 CH.sub.2 4-Cl 100-1303631 benzyl H 4-Cl 168-1703632 benzyl CH.sub.3 4-Cl 113-1153633 benzyl 2-propynyl 4-Cl Oil3635 benzyl benzyl 4-Cl 103-1053637 CH.sub.3 acetyl 3,4-Cl.sub.2 143-145__________________________________________________________________________EFFECTS ON PLANT SPECIESof Compounds of the formula ##STR10##Com-pound SaltNo. R R.sup.1 (R.sup.2)n (R.sup.3)n' Type M.P.__________________________________________________________________________ .degree.C.3299 CH.sub.3 CH.sub.2 CCH 3-Cl n' = 0 oil3300 CH.sub.3 ##STR11## 3-Cl n' = 0 oil3302 CH.sub.3 allyl 3,4-Cl.sub.2 n' = 0 90-23303 CH.sub.3 CH.sub.2 CCH 3,4-Cl.sub.2 n' = 0 oil3339 CH.sub.3 benzyl 3,4-Cl.sub.2 n' = 0 oil3348 CH.sub.2 CH.sub.2 CH.sub.2 n = 0 n' = 0 193-53340 n-butyl H3,4-Cl.sub.2 n' = 0 165-73342 CH.sub.2SCH.sub.3 H3-Cl n' = 0 crude oil3344 n-butyl CH.sub.3 3,4-Cl.sub.2 n' = 0 98-1013346 CH.sub.2SCH.sub.3 CH.sub.3 3-Cl n' = 0 77-803328 CH.sub.3 H n = 03-CH.sub.3 180-43329 CH.sub.3 CH.sub.3 n = 03-CH.sub.3 oil3331 CH.sub.3 CH.sub.3 n = 03-CH.sub.3 135-1363332 CH.sub.3 H n = 0 4,5,6,7- 265-70 tetrachloro__________________________________________________________________________EFFECTS ON PLANT SPECIESof Compounds of the formula ##STR12##Com-pound SaltNo. R R.sup.1 (R.sup.2).sub.n Type M.P. .degree.C.__________________________________________________________________________3700 CH.sub.3 CH.sub.3 4-NO.sub.2 152-1553701 benzyl H 4-NO.sub.2 182-1843702 CH.sub.2 COC.sub.6 H.sub.5 " H 149-1523703 4-pentenyl " H 79-813704 2,6-dichloro- benzyl H H 176-1783705 4-methyl- H H 163-165 benzyl3706 3-phenoxy- H H 100-103 propyl3707 benzyl CH.sub.3 4-NO.sub.2 122-1253708 benzyl 2-propynyl 4-NO.sub.2 94-973709 2,6-dichloro- benzyl CH.sub.3 H 165-1673710 4-methyl- CH.sub.3 H Oil benzyl3731 CH.sub.3 H 4-OCH.sub.3 197-1993732 C.sub.2 H.sub.5 H 4-OCH.sub.3 195-1973733 CH.sub.3 CH.sub.3 3-Cl.sub.1 4-CH.sub.3 126-1293734 C.sub.2 H.sub.5 H 3-Cl.sub.1 4-CH.sub.3 166-1683749 propyl H H 104-1063750 propyl allyl H 80-823751 isopropyl H H 132-1343752 isopropyl CH.sub.3 H dec. 853780 CH.sub.3 CH.sub.3 4-OCH.sub.3 105-1083781 C.sub.2 H.sub.5 CH.sub.3 4-OCH.sub.3 85-883782 C.sub.2 H.sub.5 CH.sub.3 ##STR13## 104-1063783 CH.sub.3 CH.sub.3 2-CH.sub.3 Oil3784 C.sub.2 H.sub.5 H 2-CH.sub.3 135-1373785 C.sub.2 H.sub.5 CH.sub.3 2-CH.sub.3 Oil3786 CH.sub.3 CH.sub.3 2-Cl Oil3787 C.sub.2 H.sub.5 H 2-Cl 116-1183788 CH.sub.3 CH.sub.3 4-F 82-853789 C.sub.2 H.sub.5 H 4-F 183-1853790 CH.sub.3 H 3-F 204-2063791 C.sub.2 H.sub.5 CH.sub.3 2-Cl Oil3792 C.sub.2 H.sub.5 CH.sub.3 4-F Oil3793 CH.sub. 3 H 2-CH.sub.3 165-168 3-Cl3794 CH.sub.3 H 4-butyl 127-1303795 C.sub.2 H.sub.5 H 4-butyl 107-1093796 CH.sub.3 CH.sub.3 4-isopropyl 111-1143797 C.sub.2 H.sub.5 H 4-C.sub.3 H.sub.7 142-1443798 CH.sub.3 CH.sub.3 2-Cl.sub.1 106-108 6-CH.sub.33799 C.sub.2 H.sub.5 H 2-Cl.sub.1 172-174 6-CH.sub.33800 benzyl H H 115-1163812 ispropyl allyl H 87-903813 butyl H H 119-1213814 butyl CH.sub.3 H dec.653815 butyl allyl H Syrup3816 isobutyl H H 137-1393849 isobutyl CH.sub.3 H dec.653850 isobutyl allyl H 62-653851 ##STR14## H H semi- solid3977 CN CH.sub.3 n = 0 dec.1454017 CH.sub.3 H 3-benzyloxy 106-1084019 CH.sub.3 H 3-NO.sub.2 191-1934020 C.sub.2 H.sub.5 H 3-NO.sub.2 192-1954021 CH.sub.3 H 4-benzyloxy 130-1334023 CH.sub.3 CH.sub.3 3-CF.sub.3 95-97 4-Cl4025 CH.sub.3 H 2-CF.sub.3 156-1594026 CH.sub.3 CH.sub.3 3-benzyloxy 83-854027 CH.sub.3 CH.sub.3 3-NO.sub.2 105-1084028 CH.sub.3 CH.sub.3 4-benzyloxy 87-904029 CH.sub.3 CH.sub.3 2,6-Cl.sub.2 Oil4030 CH.sub.3 CH.sub.3 2-CF.sub.3 Oil4033 CH.sub.3 H 3-OCH.sub.3 158-1604034 C.sub.2 H.sub.5 H 3-OCH.sub.3 103-1054035 CH.sub.3 H 3,5-(CH.sub.3).sub.2 200-2024036 C.sub.2 H.sub.5 H 3,5-(CH.sub.3).sub.2 129-1314062 2-(2,4- CH.sub.3 n = 0 108-110 dichloro- phenoxy) ethyl4063 CH.sub.3 CH.sub.3 3-OCH.sub.3 85-884064 CH.sub.3 CH.sub.3 3-SCH.sub.3 91-944065 C.sub.2 H.sub.5 H 3-SCH.sub.3 127-1294066 CH.sub.3 CH.sub.3 2-Cl.sub.1 90-92 4-CH.sub.34068 CH.sub.3 CH.sub.3 ##STR15## 109-1114070 CH.sub.3 CH.sub.3 4-COCH.sub.3 144-1454115 CH.sub.3 CH.sub.3 4-CN 175-1784116 CH.sub.3 H 4-N(C.sub.2 H.sub.5).sub.2 187-1884117 CH.sub.3 CH.sub.3 4-CF.sub.3 131-1334118 CH.sub.3 CH.sub.3 2-CH.sub.3 86-88 4-Cl4119 CH.sub.3 CH.sub.3 3,4-OCH.sub.2 O 114-1174120 CH.sub.3 CH.sub.3 2,4-Cl.sub.2 84-864121 C.sub.2 H.sub.5 H 2,4-Cl.sub.2 128-1304122 CH.sub.3 H 4-OEt 162-1654123 C.sub.2 H.sub.5 H 4-OEt 142-1444124 CH.sub.3 H2-F 139-1414125 C.sub.2 H.sub.5 H 2-F 110-1124126 CH.sub.3 CH.sub. 3 4-OEt 114-1164127 CH.sub.3 CH.sub.3 2-F 87-894128 C.sub.2 H.sub.5 CH.sub.3 2,4-Cl.sub.2 86-884129 C.sub.2 H.sub.5 CH.sub.3 4-OEt 102-1064130 C.sub.2 H.sub.5 CH.sub.3 2-F 79-814259 CH.sub.3 CH.sub.3 3,4-CH.sub.2 CH.sub.2 CH.sub.2 Semi- solid4261 CH.sub.3 CH.sub.3 3-COOEt 143-1464262 C.sub.2 H.sub.5 CH.sub.3 3,4-CH.sub.2 CH.sub.2 CH.sub.2 Oil4263 C.sub.2 H.sub.5 CH.sub.3 3-COOEt 98-1014264 propyl CH.sub.3 2,4-Cl.sub.2 85-874290 CH.sub.2 CHCH.sub.2 CH.sub.3 4-CF.sub.3 Oil4291 2-(2,4- CH.sub.3 2-F Oil dichloro- phenoxy) ethyl4292 CH.sub.2 CHCH.sub.2 CH.sub.3 3,4-OCH.sub.2 O Oil4293 4-fluoro- H 4-F 98-101 benzoyl- methyl4329 1-benzoyl- CH.sub.3 4-OCH.sub.3 80-83 ethyl4330 4-fluoro- CH.sub.3 2-CH.sub.3 78-81 benzoyl- methyl4331 4-fluoro- CH.sub.3 2-Cl 75-78 benzoyl- methyl4332 4-fluoro- CH.sub.3 2-F 60-63 benzoyl- methyl4333 2-(N-ethyl- H n = 0 184-186 N-phenyl- carbamyl) ethyl4355 CH.sub.2 COOH CH.sub.3 n = 0 HBr 115-1204373 CH.sub.3 2-phenoxy- ethyl n = 0 Glass4374 CH.sub.3 CH.sub.2 CH.sub.2 OCHCH.sub.2 n = 0 147-149 dec.4375 CH.sub.3 3-chlorobenzyl n = 0 Glass4429 CH.sub.3 isopropyl n = 0 116-1184230 C.sub.2 H.sub.5 isopropyl n = 0 170-1724496 4-pyridyl- H n = 0 183-185 methyl4497 2-pyridyl- H n = 0 168-171 methyl4498 3-pyridyl- H n = 0 202-205 methyl4499 4-pyridyl- H 3-F 75-80 methyl4500 2-pyridyl- H 3-F 195-197 methyl4501 3-pyridyl- H 3-F 183-186 methyl4502 4-pyridyl- CH.sub.3 n = 0 110-115 methyl4503 3-pyridyl- CH.sub.3 n = 0 79-81 methyl4504 2-pyridyl- CH.sub.3 3-F 109-112 methyl4505 3-pyridyl- CH.sub.3 3-F 170-175 methyl4455 ##STR16## H n = 0 213-2154456 C(CH.sub.3).sub.2 H n = 0 193-196 benzoyl4457 3-phenyl- CH.sub.3 n = 0 Oil allyl4458 3-phenyl- H 3F Oil allyl4459 C(CH.sub.3).sub.2 H 3F 150-153 benzoyl4460 CH.sub.2 CH.sub.2 CFCF.sub.2 H n = 0 110-1124461 2-(N-ethyl- CH.sub.3 3-F Oil N-phenyl- carbamyl) ethyl4462 CH.sub.2 CH.sub.2 CFCF.sub.2 CH.sub.3 3-F 60-624463 CH.sub.2 CH.sub.2 CFCF.sub.2 CH.sub.3 n = 0 Oil4313 CH.sub.3 CH.sub.3 n = 0 134-1384359 CH.sub.3 C.sub.2 H.sub.5 n = 0 114-1164360 C.sub.2 H.sub.5 C.sub.2 H.sub.5 n = 0 107-108__________________________________________________________________________EFFECTS ON PLANTS SPECIESof Compounds of the formula ##STR17##Com-poundNo. R R.sup.1 Ar (R.sup.2).sub.n M.P. .degree.C.__________________________________________________________________________4258 CH.sub.3 CH.sub.3 3-methyl- 169-172 benzoyl__________________________________________________________________________EFFECTS ON PLANT SPECIESof Compounds of the formula ##STR18##Com- Preemergent Effects Postemergent Effectspound Crab- Cox- Sugar Al- Sugar Toma- Comments onNo. grass comb Brome Millet Radish Beet Millet falfa Oat Radish Beet to Utility__________________________________________________________________________2878 K4 F3G3 F3G3 F3G3 F3G2 K4 N2G3 F3G2 0 N2G1 F2G2 F3 Increases chlorophyl in foliage. F1 F1 F2 Increases chlorophyl2960 F3G3 F3G3 F3G3 F3G3 F3G2 K4 N2G2 F2G2 N1G1 N1G2 F1G2 F2 in foliage. Epinesty on alfalfa.2961 K4 F3G3 F3G3 F3G3 F2G2 K4 N2G2 F2G2 F2G2 F2G3 FIG2 F3G2 Increases pod set of soybeans.3062 0 0 0 0 0 0 0 0 0 0 F2G2 03099 F3G3 F2G2 F3G3 F3G3 F3G2 K4 F1G2 F3G2 F1G1 F3G2 F1G3 N1F2 Defoliates cotton. F2 F2 Kills pigweed.3100 K4 F2G2 F3G3 F3G3 F2G2 K4 N1G1 F3G2 N1 N1G2 F2G2 F3 Defoliates cotton. F2 F2 F1 Kills pigweed.3101 F3G2 F2G1 F3G3 F2G3 F2G1 F2G2 N1G1 N2G2 N1F2 N1G2 F2G2 F2G1 Defoliates cotton. F1 Kills pigweed.3102 F2G1 F1G1 F2 F3G2 FIG1 F1 N1G1 F2G1 N1F1 F2G2 F2G2 F3G13104 F1G1 0 F2 F2 F1 F1 N1 F1 N1G1 F1 F2G1 F2 F33105 F3G3 F2G1 F3G3 F3G3 F3G2 K4 N1G3 F3G2 N1F1 F1G2 F2G2 F2 Defoliates cotton. F1 Kills pigweed.3110 K4 F2G1 F3G2 F3G3 F2G2 K4 N1G2 F2G2 N1G1 F1G1 F2G2 F2 Controls pigweed. F23111 F3G3 F2G1 F3G3 F3G3 F2G1 K4 N1G2 F3G2 F2 F2G2 F2G2 F3G2 Promotes tillering of oats.3129 0 0 0 0 0 0 0 0 0 0 N1F1 03130 F2 0 F2 F3 Kills lambsquarter (post-emerg.)3134 0 0 0 0 0 0 0 F1 N1 0 F2G1 F23135 F1G1 0 F1 F2G2 G2 0 F2G1 F2 F1 F1 F2G2 F3 F2 F3 F2 F2 Defoliates cotton.3141 K4 F3G3 K4 K4 F3G3 K4 N3G3 N2G3 F1G2 N2G3 N2G3 F3 Kills pigweed. F23143 F3G3 F2G2 F3G3 F3G3 F2G2 K4 N2G3 F3G2 F1 F2G2 F2G1 F3G1 Controls pigweed. F1 F2 Defoliates cotton.3144 K4 N4 F3G3 F3G3 F2G2 F2G1 N2G1 F3G2 N1F1 N1G2 F2G2 F3 Kills pigweed. F13171 0 0 0 0 0 0 0 F1 N1 N1G1 F1 F23176 F3G3 F3G3 F3G3 F3G3 F2G2 F3G3 F2 F3G2 N1F2 F1 F2G3 F3 Promotes tillering of oats3191 F1G1 F1 F3G1 F3G3 F3G2 F3G2 N1F1 F2 F1 F2 F2G2 F23192 0 0 0 0 0 0 0 0 0 0 F1 03193 0 0 F2 0 0 0 0 F1 F1 F1 F1G3 0 F3 F33205 K4 K4 F3G3 F3G3 F3G2 F3G3 N3G3 G3 F1G2 F2G2 F2G3 F3 F23206 F3G3 F3G3 F3G3 F3G3 F3G2 K4 N1G2 F2G3 0 F2G2 F2G3 F33215 F3G2 F2G1 F3G3 F3G2 F2G2 F3G3 0 G2F3 F1 F2 F2G2 F3G13216 F3G3 F3G3 K4 F3G3 F3G2 F3G3 F1 F3 F2 F2 F2G3 F2 Increases tomato fruit set.(Heart F2 shaped fruit)3218 0 0 F1 0 0 0 0 N1G2 0 N1 F3G2 03219 F1G1 0 F2 0 0 0 N1 F3G2 F1 F1 F2G2 F1 F33220 F3G3 F2G2 K4 F3G3 F3G3 F2G2 N1G2 F3G2 F1 F1G1 F3G3 F3G13221 F3G3 F3G3 F3G2 F3G3 F3G2 F2G2 F1 F1G1 F1 F2 F2G2 F1G13222 F1 0 F1 0 0 0 0 F2G1 0 0 F1G2 0 Increases tomato fruit set.3251 0 0 0 0 0 0 0 F1 0 0 0 03274 F1 0 F2 F2 F1 0 N1 N1F1 0 N1G1 F2G3 N1F13276 0 0 F2 F2 0 0 0 F2 0 F1 F2G2 0 F23277 F3G3 F2G2 F3G3 F3G3 F3G2 F3G2 F1G1 F3G3 F1G1 F2G1 N2G3 F2 Increases tomato fruit set, tiller-3278 F2G1 F2 F2 F2G1 F1G1 F1G1 0 F2G1 F1 0 F3G2 0 ing of oats.3292 F3G3 F3G2 F3G3 F3G3 F3G3 F3G3 N1G2 F3G2 F2 F3G2 F2G3 F2 Increases fruit set on tomatoes,3293 tillering of oats, controls crabgrass.3294 F2G2 F2G2 F3G3 F3G2 F2G2 K4 F1G1 F3G2 F2 F3G2 F3G2 F1 Increases tomato fruit set, tiller- ing of oats, con- trols crabgrass.3295 F2 F1 F2 F1 F1 F1 0 F3G2 F1 F2G2 F3G3 F2 Increases tiller- ing of oats.3296 0 0 F1 F1 0 0 0 F1 0 0 F2G2 03297 0 0 0 0 0 0 0 F1 0 0 F1G1 F13298__________________________________________________________________________EFFECTS ON PLANT SPECIES -of Compounds of the formula ##STR19##Com- Preemergent Effects Postemergent Effectspound Crab- Cox- Sugar Al- Sugar Toma- Comments onNo. grass comb Brome Millet Radish Beet Millet falfa Oat Radish Beet to Utility__________________________________________________________________________3283 F1 F1 F2 F2G2 F1 F1 0 0 0 F1G1 F2G3 N13287 0 F1 F1 F2G1 F1G1 F1G1 0 0 F1 0 F1G2 N1 F2 F13409 F3G3 K4 K4 F3G3 F3G3 K4 N1G2 F3G3 N1G1 F3G3 F3G2 F3 F23410 F3G3 K4 K4 F3G3 F3G3 K4 N1G2 F3G3 G2 F2G2 F3G3 F3 F13411 F3G3 K4 K4 F3G3 K4 K4 N2G3 F3G2 G2F1 N2G3 F2G3 F2G33497 F2G2 F1 F3G1 F3G1 F1G1 F2G1 0 F2G1 0 N1 F3G1 F33500 F1G1 F2G1 F3G2 F2G2 F2G2 F2G2 F1G1 F2G1 F1G1 F1 F3G1 F23672 F1G1 K4 F3G3 F1G1 F2G2 F3G2 0 F2G1 F1G1 F2G1 F3G2 F2 Increases fruit set3628 F3G3 F3G3 K4 F3G3 F3G2 F3G3 G2F1 F3G3 G2F1 F2G1 F3G2 F3 Increases fruit set3629 0 0 F2 0 0 0 0 F1 0 F1 F2 F13631 0 0 F2 0 0 0 0 F1 0 0 F2 03632 F3G3 F2G2 K4 F3G2 F3G2 F3G2 G1 F3 G1 F1G1 F3G1 F3G2 Increases fruit set3633 F3G2 F2G1 F3G3 F2G1 F3G2 F2G1 0 F2 0 F1 F3G1 F3G1 Increases fruit set3635 0 F1 F2 0 F1 F1 0 F2 0 F1 F2G2 F2 Increases fruit set3637 0 0 0 0 0 0 0 F2 0 F1 F2 0__________________________________________________________________________EFFECTS ON PLANT SPECIESof Compounds of the formula ##STR20##Com- Preemergent Effects Postemergent Effectspound Crab- Cox- Sugar Al- Sugar Toma- Comments onNo. grass comb Brome Millet Radish Beet Millet falfa Oat Radish Beet to Utility__________________________________________________________________________3299 F1 F1 F2 F1 F1 F1 0 F2G1 0 F1 F2G3 03300 0 0 0 0 0 0 N1 F1 0 0 F2G3 03302 0 0 0 0 0 0 0 F2 0 0 F1G1 03303 0 0 0 0 0 0 0 F2 0 0 F1G1 03339 0 0 0 0 0 0 0 0 0 0 F1 F13348 0 0 0 0 0 0 0 0 0 0 F1 F13340 0 0 0 0 0 0 0 0 0 0 F1 F13342 0 F1 F2 0 F1 F1G1 0 F2G1 0 F1 F3G3 03344 F1G1 F2G1 F3G3 F1 F1G1 F3G3 0 F2 0 F2 F3G3 F1 Increased fruit set3346 F3G3 K4 F3G3 F3G2 F2G2 K4 F2 F3G2 F2G1 F2G1 F2G3 F2 Increased fruit set3328 0 0 0 0 N1 0 0 0 0 0 F1 03329 F2G2 F3G3 F3G3 F3G3 F3G2 F2G2 F1G2 F3G2 F1 N1F2 F3G2 N1F13331 K4 F3G3 F3G3 K4 F3G3 F3G3 N2G3 F3G3 F1 F2G2 F3G2 F13332 0 0 0 0 0 0 0 0 0 0 F1 0__________________________________________________________________________EFFECTS ON PLANT SPECIESof Compounds of the formula ##STR21##Com- Preemergent Effects Postemergent Effectspound Crab- Cox- Sugar Al- Sugar Toma- Comments onNo. grass comb Brome Millet Radish Beet Millet falfa Oat Radish Beet to Utility__________________________________________________________________________3700 0 0 F1 0 0 0 0 F1 F2 F2G2 F3G2 F2 Oat tillered in- creased fruit set3701 0 0 0 0 0 0 0 G2F1 0 F1 F2 N13702 0 0 F1 0 0 0 0 F1 F1 F1 F3 N13703 0 0 0 0 0 0 0 F2G2 F1 0 F3 0 F23704 0 0 0 0 0 0 0 0 -- 0 0 N1G1 All plants taller except tomato3705 0 0 0 0 0 0 N1 F2 0 F1 N1F1 F13706 0 0 0 0 0 0 0 F2 0 F1 F3G1 F1 Alfalfa very tall3707 0 0 0 0 0 0 0 F1 0 F1 F2G2 F2 Increased fruit set3708 0 0 0 0 0 0 0 0 0 F1 F2 03709 F2G1 F2G1 F2 F1G1 F3G3 F2G1 0 F2G1 0 F1 F3G2 F2 Increased fruit set3710 F3G3 F3G2 F3G3 F3G2 F3G3 F3G3 F2G1 F3G1 F2 F2G2 F3G2 F2G1 Increased fruit set and oat tillers3731 0 F1 F2 0 G1 F2 0 F2 F1 F1 F3 N1F2 Increased fruit set3732 0 0 0 0 0 0 0 0 0 0 F2 03733 0 0 0 0 0 0 0 F1 0 F2 F3G1 F2 Increases fruit set3734 0 0 0 0 0 0 0 0 0 0 F1 03749 0 0 0 0 0 0 0 0 0 0 F3G1 03750 F1 F1 F3G3 F2G2 F1 F1 0 F2G2 F1N1 F2G1 F3G1 F2G2 Increased oat tillered fruit set3751 0 0 0 0 0 0 0 F1 0 0 F1 N13752 K4 F1G1 K4 F2G2 F2G2 K4 F1G3 F2G3 G1 F2 F2G1 F3 Increased fruit F2 set3780 F1 F2G1 F3G3 F2G1 F2G2 F2G1 N1 F2G2 N1 N1G2 F3G1 F1 F23781 F2G1 -- K4 F2G2 F3G2 F2G2 0 F3G2 F2 N2G2 F3 N1F23782 0 F1 F2 0 0 F1 0 F2 0 F2 F3 N1F1 Increased fruit set3783 F1 F1 F3G2 F2G2 F2G1 F2 N1G1 N1 G1 F1G1 F2G2 F2 Increased fruit set3784 0 0 F1 0 0 0 0 0 0 0 F2G1 F13785 F2G1 F2G2 F3G3 F3G2 F3G3 F3G2 N1G2 F2G2 G1 F2G2 F3G2 F2G1 Increases fruit set3786 F1G1 F3G3 F3G3 F2G2 F3G3 F3G2 F1G1 F1 -- F2 F3G1 F2 Increases fruit set3787 0 0 F1 0 0 0 N1 0 0 F1 F2G1 N1 F2 F1 Increases fruit3788 F3G3 K4 K4 F3G2 K4 K4 F3G2 F2G3 N1G2 N1G3 N1G2 F2 set3789 0 F1 F1 0 0 0 0 F1 0 0 F2G1 03790 0 0 F2 0 0 0 0 F3 0 0 F1G2 N1F1 Increases fruit set3791 F2G1 F2G2 F3G2 F2G2 F2G2 F3G2 0 F1 G1 N1G1 F2G2 F2G1 Increases fruit set3792 F1G1 F2G1 F3G3 F3G3 F3G3 K4 F2G2 F2G3 G1F1 F3G3 F2G2 F2G2 Increases fruit set3793 0 0 F1 0 0 F1 0 0 0 F1G1 F2G1 03794 0 0 F2 0 0 F1 0 F1 0 F1 F1G1 03795 0 0 0 0 0 0 0 0 0 0 F1 F13796 0 0 K3G3 0 0 F1 0 0 0 F2 F2G2 F2 Increases fruit set3797 0 0 F1 0 0 K3G3 0 0 0 0 F1 03798 0 0 0 0 0 0 0 0 0 0 F1 03799 G1 0 N3G1 0 0 0 0 0 0 F1 F1 03800 0 0 F2 0 0 F1 0 0 0 0 -- N13812 F2G2 F3G3 K4 F2G2 F2G2 F3G3 F1G1 F3G1 F1G1 F1 F3G2 F2 Increased tillers, fruit set3813 0 F1 F2 0 0 F1 0 F2 0 F1 F2 03814 F3G3 K4 K4 F3G2 F3G3 F3G3 F2G2 F3G3 F2G2 F3G2 F3G3 F3G1 Increased tillers, fruit set3815 K4 K4 K4 F3G3 F3G3 K4 G1 F3G2 F1G1 F1 F3G1 F2 Increased fruit set3816 0 -- F2G1 0 0 0 0 F1 0 0 0 03849 F2G2 F3G2 F3G3 F1G2 F2G2 F2G2 F3G2 F3G3 F2G2 F2G2 F3G3 F3G1 Increased fruit set, tillers3850 0 F1G1 F3G1 G1 0 F1 F1 F3 F1 F1 F2G1 F3 Increased fruit set3851 0 0 0 0 0 0 0 F1 0 0 F1 F13977 0 F1 F2G1 0 F1 F2 0 F2 N2G2 F1 F3 F34017 0 0 0 0 0 0 0 F2 0 0 F1 F14019 0 0 0 0 0 F1 0 F1 0 0 F1 F1 Increases fruit set4020 0 F1 0 0 0 F1 0 0 0 0 F1 F1 Increases fruit set4021 0 -- 0 N1 0 N1 0 0 0 0 0 04023 F1 F2G2 F2G1 F1G1 F2G1 F3G2 F1 F2G1 F2G1 F3G1 F3G1 F2 Increases fruit set, tillers4025 0 F1 F2 0 0 F1 F1G1 F2G1 F1 F1 F2G2 F1 Increases fruit set, tillers4026 0 F1 F2 0 0 G2F2 F1 F2 F1 F2 F1 F24027 F2G2 N4 N4 F2G2 F2G1 F3G1 F2G1 F3G1 F1G1 F2G1 F3G2 F3E1 Increased fruit set, elongated growth4028 0 0 F2 0 F1 F2 F1 F3G1 F1 F2 F2G1 F14029 0 0 F1 0 0 F1 0 0 0 0 0 04030 F1G1 F2G2 F3G3 F1G1 F3G3 F3G3 F2G1 F3G1 F2G2 F3G2 F3G2 F3G1 Increased fruit set, tillers4033 0 0 0 0 0 0 0 F1 0 0 F1 F1 Increased fruit set4034 0 0 0 0 0 0 0 0 0 0 F1 F14035 0 0 0 0 0 F1 0 F1 0 0 F1 F1 Increased fruit set4036 0 0 0 0 0 0 0 0 0 0 N2F1 F14062 F2G2 F3G2 F3G3 F3G2 F3G2 F3G3 F1 F3G2 F1 F3G2 F2G1 F3E1 Increased fruit set, elongated growth4063 F3G3 F3G2 K4 F3G3 F3G3 F3G2 F2G2 F3G2 F2G1 F2G2 F3G3 F3G1 Increased fruit set and tillers4064 F3G3 N4 F3G2 F2G1 F2G1 F2G1 F1G1 F3G2 F1G1 F2G2 F3G2 F3G1 Fruit set, tillers4065 0 0 0 0 0 0 0 F1 0 0 0 04066 0 F1 F2 F1 F1 F2G1 0 F1 0 0 F1 0 More fruit set4068 F2G2 F1G1 F2 F1G1 G1 F1G1 0 F2 F1 F1 F1 F3 Fruit set tillers4070 F1G1 0 F1 0 0 F1 0 F1 0 0 F1 F1 Fruit set4115 F1G1 F1 F2 F2G1 F2G2 F3G1 F1 F1 F1 F1 F1 F2 Fruit set4116 0 0 0 0 0 F1 0 0 0 F1 F1 F1 Fruit set4117 F2G1 F2 F2G1 F2G2 F2G2 F2G1 F1G1 F2G2 F1 F2G1 N4 F34118 F2G2 F2G1 F3G2 F3G2 F2G2 F2G2 F2G2 F2G1 F2G1 F2 F2G1 F3 Fruit set, tillers4119 G1 F1 F1 0 F1 F1 F1G1 F3G2 F2G1 F2 F3G2 F3G1 Fruit set, tillers4120 F1G1 F1 F3G1 F2G1 F2G1 F3G2 F2G1 F3G2 F2G1 F2G2 F3G2 F3 Fruit set, tillers4121 0 F1 F1G1 0 F1 F2G1 F1 F2 F1G1 F1 F2 F2 Inc. fruit set, tillers4122 G1 F1 F2G1 0 0 F2G1 F1G1 F3G2 F1G1 F1 F2 F3G1 Tillers4123 0 0 0 0 0 0 0 0 0 0 F1 04124 0 0 F1 0 0 F1 0 F1 F1 F1 F1 F1 Good fruit set4125 0 0 0 0 0 0 0 F1 F1 0 F1 F1 Fruit set4126 F1 F2 F3G1 F2G1 F2G1 F3G1 F1G1 F3G1 F2G1 F2G2 F1G1 F3G3 Dark green, tillers4127 F2G2 F3G2 F3G3 F3G2 F3G3 F2G1 F2G2 F3G2 F2G1 F1G1 F2G1 F3G1 Fruit set, tillers4128 F1G1 F2G1 F3G2 F3G2 F2G2 F2G1 F1G1 F2G1 F1 F2G2 F2G1 F3 Fruit set4129 F2G1 F3G3 F3G3 F2G1 F2G2 F2G2 F1 F2 0 F1 F2 F3 Fruit set4130 F2G2 F3G2 F3G3 F3G2 F3G3 F3G3 F2G2 F2G1 F1 F2G1 F2G2 F3 Fruit set4259 0 0 F1 0 0 0 F1G1 F2G1 F1 F1G1 F2 F3G1 Fruit set4261 0 0 0 0 0 0 0 0 0 0 F1 04262 0 F1 F2 F1G1 F2 F2 0 F1 0 F1G1 F2G1 F3 Fruit set4263 0 0 0 0 0 0 0 0 -- 0 F1 04264 0 F1 F3 F1 F1 F2 F1G1 F2G1 F1 F1G1 F3G1 F3G1 Fruit set4290 F3G2 F2G2 F3G3 F3G2 F2G2 F3G2 F2G1 F3G2 -- F2G2 F3G3 F3G3 Fruit set GW24291 F3G3 F3G3 F3G2 F3G3 K4 K4 F3G3 F3G3 -- F3G3 F3G3 F3E34292 0 F1 F1 F1 0 0 F1 F3G2 F1 F1 F2G2 F34293 0 0 F1 0 0 0 0 F1 0 0 F1 04329 F2G1 K4 F2G1 F1G1 F1 F3G1 N2G1 F3G2 F1 F1 F2 F34330 F3G2 F2 F3G1 F3G2 F2G1 F3G1 F1G1 F2 F1 F1 F2 F3 Fruit set4331 F2G2 F1 F3G1 F2G1 F1 F2G1 N1G1 F1 F1 F1 F2 F2 Fruit set4332 F3G2 F2G1 F3G2 F3G2 F3G3 F3G3 F2G2 F3G3 F2G1 F2 F3G2 F3 Fruit set oat tillers4333 F2G1 F2 F3G1 F2G1 F1 F2G1 F1G1 F3G2 F1 F2 F2G1 F1 Tillers4355 F3G3 F3G3 F3G3 F3G2 F3G2 F3G3 N2G2 F3G3 F1 N1G1 N4 F2N1 Tillers4373 F1 F2G2 F2 F2G1 0 F2G1 0 F1 F1 F1 F1G1 F2 Fruit set tillers4374 G1 G1 0 0 0 F2 0 F1 0 0 F1 F1 Fruit set G14375 0 F2 F1 F1 F1G1 F2G1 N1 F2 0 N2F1 F3G2 F2 Fruit set4429 0 F1 0 F1 F2 F2 Fruit set4230 0 0 0 0 0 0 0 0 0 0 0 F14496 0 F1 F1 0 0 F1 N1 F1 0 N1 F1 F14497 0 0 0 0 0 0 0 F3G2 F1 F1 F2G1 F14498 0 0 0 0 0 0 0 0 0 F1 F1 F14499 0 0 0 0 0 0 N1F1 F3G3 F1 F1 F1 F14500 0 0 0 0 0 0 0 0 0 0 F1 F24501 0 0 F1 0 0 0 F1 F3G2 F1 F1 F2G1 F2 Increased fruit set4502 F2G2 F2G2 F3G2 F3G2 F2G2 F1G1 F2G1 F3G3 F2 F2 F2G1 F3 Increased fruit set4503 K4 F3G3 K4 F3G3 F3G3 K4 F3G2 F3G3 F2G1 F3G3 F3G2 F3 Increased fruit set4504 K4 K4 F3G3 F3G3 F3G3 F3G3 F2G2 F3G3 F2G1 F2G2 F2G1 F3 Increased fruit set4505 F3G3 K4 F3G3 F3G2 F3G2 F3G2 F2G2 F3G3 F2G1 F2G1 F3G1 F3 Increased fruit set4455 0 F1 0 F1 F1 04456 0 F2G2 0 F1 F1 F14457 F2G1 F3G2 F2 F2 F2G1 F3 Tillers4458 F2G1 F3G3 F2 F1 F2 F3 Tillers4459 0 F1 0 F1 F2 F14460 N1G1 F2G1 0 F1 F1 04461 N2G2 F3G3 F2 F3G2 F3G2 F3G1 Fruit set, tillers4462 N1G1 F3G3 F2 F2 F3G2 F2 Fruit set, tillers4463 N1G1 F3G3 F2G1 F2G1 F3G2 F3G1 Fruit set, tillers4313 F1G1 G1 0 F1G1 0 F2G1 0 0 0 0 F1 04359 F1 -- F2 F2G2 F1 F3G1 0 F1G1 0 F1G1 F1G1 F1 Fruit set4360 0 F1 F1 F2G1 0 F1 0 F1 0 F1 F1 F1 Fruit__________________________________________________________________________ setEFFECTS ON PLANT SPECIESof Compounds of the formula ##STR22##Com- Preemergent Effects Postemergent Effectspound Crab- Cox- Sugar Al- Sugar Toma- Comments onNo. grass comb Brome Millet Radish Beet Millet falfa Oat Radish Beet to Utility__________________________________________________________________________4258 0 0 F1 0 0 0 F1G1 F2G1 F1 F1G1 F2 F3G1 Increased fruit set__________________________________________________________________________
The use of many of the growth regulator compounds may be demonstrated by treatment of soybeans (Soja max) to increase the number of seed pods and by treating tomato plants (Lycopersicum esculentum) to increase fruit set. In an illustrative experiment, Soja max (Evans variety) and Lycopersicum esculentum (Tiny Tim variety) were grown in 4-inch pots (one plant per pot) filled with greenhouse potting soil (2 parts good top soil, 11/2 parts builder's sand, 11/2 parts peat, fertilized with 5 lb. of 12-12-6 fertilizer and 5 lb. of finely ground limestone per cu. yd.). Aqueous spray formulations were prepared and the potted plants were sprayed at a spray volume of 40 gal. per acre and at application rates of 16, 4, 1 and 1/4 oz. per acre. The spray mixtures were prepared by dissolving the proper amount of growth regulator compound in 15 ml. of acetone, adding 2 ml. of a solvent-emulsifier mixture consisting of 60 wt. percent of a commercial polyoxyethylated vegetable oil emulsifier (96 wt. percent active ingredient, Emulphor EL-719), 20 wt. percent xylene and 20 wt. percent deodorized kerosene, then bringing total volume up to 80 ml by addition of a 0.156 wt. percent aqueous solution of liquid non-ionic dispersant (90 wt. percent active trimethylnonyl polyethylene glycol ether, Tergitol TMN-10). Two replicates were sprayed at all application rates. For comparative purposes, plants were also sprayed at 40 gal./acre with water. The number of seed pods and of fruit as percentage of arithmetic mean of the numbers on untreated plants was observed within approximately three weeks after spray treatment and the results are tabulated below. The extent of growth regulatory effect on the plants was estimated on a scale of 0 to 10 and is also recorded in the following table:
______________________________________GROWTH REGULATING EFFECTS ON TWO SPECIES Lycopersicum Soja max esculentum Severity Severity Pod Count.sup.1 of Fruit Count of Percent in Growth Percent in GrowthCom- Rate Comparison Regula- Comparison Regula-pound oz/ to Untreated ting to Untreated tingNo. A Plants Effect.sup.2 Plants Effect.sup.2______________________________________2878 16 163 a,c 9 73 a,b 9 4 183 a,c 6.5 364 a,b 9 1 117 3 327 42960 16 160 a,c 9 218 a 9 4 138 6.5 218 e 7 1 135 6.5 327 23099 16 183 a,c 9 182 b 9 4 177 a,c 6.5 400 b 8 1 186 2.5 436 b 4.53100 16 166 a,c 9 82 a 9 4 166 6.5 382 e 6.5 1 146 4 355 43105 16 185 a,c 9 136 9 4 171 7 382 6.5 1 143 4 355 33143 16 166 a,c 9 245 a 9 4 169 6 191 d 7.5 1 157 2 191 e 3.53144 16 199 a,c 9 55 a 9 4 157 5.5 382 d 7 1 157 2.5 245 e 53176 16 111 2 178 b 7.5 4 104 0 141 3 1 93 0 131 13251 16 86 0 129 0.5 4 95 0 64 0 1 91 0 64 03274 16 114 0.5 107 0 4 105 1 150 0 1 86 0 86 03277 16 146 6.5 197 b 8.5 4 143 4.5 169 5.5 1 154 2 122 1.53278 16 95 0 150 0.5 4 91 0 107 0 1 100 0 64 03293 16 154 7.5 141 b 8 4 150 3.5 178 4.5 1 121 1 113 2.53294 16 154 a 7.5 197 d 7.5 4 121 c 4.5 169 b 3.5 1 154 1.5 122 2.53295 16 136 8 216 8 4 175 4 188 3 1 145 2 169 1.53297 16 139 1 113 0.5 4 132 0 122 0 1 114 0 84 03298 16 107 0.5 113 2 4 118 0 141 0.5 1 107 0 103 03299 16 118 1 279 2 4 109 0.5 64 0 1 86 0 21 03300 16 109 1 86 0 4 114 0 129 0 1 86 0 107 03302 16 86 1.5 107 1.5 4 127 0.5 107 0 1 118 0 86 03303 16 118 1.5 193 0.5 4 123 1 43 0 1 123 0 107 03339 16 107 0 94 0 4 111 0 131 0 1 114 0 103 03340 16 105 0 150 0 4 105 0 171 0 1 114 0 193 03342 16 140 3 400 0 4 105 0.5 200 0 1 94 0 0 03344 16 136 c 6 364 4 4 145 3 321 2.5 1 114 1.5 300 23345 16 143 5 169 b 4.5 4 164 3.5 188 2.5 1 -- 1 159 13346 16 159 a 7 300 a 8.5 4 141 c 5 279 b 8 1 123 2.5 364 4.53410 16 114 a.sup.1 7.5 407 a,d 8 4 141 c.sup.1 5.5 343 b,d 7.5 1 105 .sup.1 3 321 53497 16 121 0.5 141 1 4 111 0 103 0 1 111 0 122 03627 16 121 4.5 159 2 4 104 2.5 141 2.5 1 100 1 141 1.53628 16 125 a 6.5 159 b 8 4 150 c 6 188 d 7.5 1 136 2.5 169 3.53631 16 129 1.5 122 0.5 4 104 0 84 0 1 107 0 103 03632 16 132 a 7.5 178 b 7.5 4 146 4.5 216 d 6 1 143 2.5 169 4.53633 16 143 2.5 700 3 4 129 0.5 400 0.5 1 112 0 0 03637 16 127 1.5 107 0 4 136 0 129 0 1 95 0 86 03700 16 143 4 159 4.5 4 121 2.5 150 3.5 1 104 0 141 13706 16 105 0.5 21 0 4 109 0 64 0 1 82 0 86 03707 16 123 2 300 3 4 150 1 150 1 1 136 0 129 03709 16 109 c 5.5 300 2.5 4 145 4 364 1 1 114 0.5 321 0.53710 16 167 a 8.5 900 a 8 4 136 c 5 700 b 5.5 1 143 3.5 700 4.53751 16 90 0 75 0 4 93 0 300 0 1 93 0 75 03752 16 183 8 225 9 4 153 4.5 600 8.5 1 161 2.5 975 53789 16 93 0.5 75 0.5 4 117 0 75 0 1 93 0 150 03792 16 145 8 525 9 4 123 4 1050 7 1 117 2 675 4.53812 16 106 3 392.sup.1,2 1.5 4 95 1 485.sup.2 1.5 1 106 0 369.sup.2 13849 16 166 a 7.5 254 d 8.5 4 166 c 5 692 b 6 1 127 3 438 4.53850 16 113 2 277 3 4 113 0 485 2.5 1 120 0 369 13952 16 82 2 129 0 4 105 0.5 129 0 1 105 0 64 03977 16 137 5 1000 7 4 119 1.5 550 2.5 1 112 0 250 14062 16 133 a 7 236 b 4 4 142 c 5 139 1.5 1 146 2.5 161 1.54120 16 100 a 4.5 214 4.5 4 142 c 2.5 139 4 1 117 1 129 24121 16 158 3 129 1 4 142 0.5 107 0.5 1 121 0 86 04122 16 125 5 96 1.5 4 117 2.5 96 1 1 96 0.5 139 04123 16 104 0 139 0.5 4 100 0 118 0 1 113 0 150 04124 16 121 4.5 139 1 4 113 0.5 129 0 1 104 0 139 04125 16 113 1.5 129 0.5 4 113 0 161 0.5 1 88 0 107 0______________________________________ .sup.1 Check = 100 .sup.2 Greenhouse rating on scale of 0, no effect to 10, total kill. .sup.a injury .sup.b malformed fruit .sup.c smaller pods .sup.d increased growth .sup.e pear-shaped fruit
The information presented in tabular form herein will enable a worker in the art to make a selection from among the growth regulant compounds of the invention and to make some judgment with regard to application rates, depending upon the effect which is desired. It may be seen, for example, that total kills of some species of vegetation may occur at application rates as high as 5 to 10 lb. per acre, whereas beneficial effects may be observed on living plants at application rates of 1 lb. per acre or less.
The growth regulant compounds are usually applied in combination with inert carriers or diluents, as in aqueous sprays, granules and dust formulations in accordance with established practice in the art. An aqueous spray is usually prepared by mixing a wettable powder or emulsifiable concentrate formulation of a growth regulant with a relatively large amount of water to form a dispersion.
Wettable powders comprise intimate, finely divided mixtures of growth regulant compounds, inert solid carriers and surface active agents. The inert solid carrier is usually chosen from among the attapulgite clays, the kaolin clays, the montmorillonite clays, the diatomaceous earths, finely divided silica and purified silicates. Effective surfactants, which have wetting, penetrating and dispersing ability are usually present in a wettable powder formulation in proportions of from 0.5 to about 10 percent by weight. Among the surface active agents commonly used for this purpose are the sulfonated lignins, naphthalenesulfonates and condensed naphthalenesulfonates, alkylbenzenesulfonates, alkyl sulfates and non-ionic surfactants such as products of condensation of ethylene oxide with alkylphenols.
Emulsifiable concentrates of the growth regulant compounds comprise in each instance, a solution of growth regulant compound in a liquid carrier which is a mixture of water-immiscible solvent and surfactants, including emulsifiers. Useful solvents include aromatic hydrocarbon solvents such as the xylenes, alkylnaphthalenes, petroleum distillates, terpene solvents, ether-alcohols and organic ester solvents. Suitable emulsifiers, dispersing and wetting agents may be selected from the same classes of products which are employed in formulating wettable powders.
Usually, the growth regulators are applied by diluting with water agricultural compositions which desirably contain from 0.1 percent to 95 percent by weight of active compound and from 0.1 to 75 percent of a carrier or surfactant. However, direct application to plant seeds prior to planting may be accomplished in some instances by mixing powdered solid growth regulator with seed to obtain a substantially uniform coating which is very thin and comprises only one or two percent by weight or less, based on the weight of the seed. In most instances, however, a nonphytotoxic solvents, such as methanol is employed as a carrier to facilitate the uniform distribution of growth regulator on the surface of the seed.
When a compound is to be applied to the soil, as for a pre-emergence application, granular formulations are sometimes more convenient than sprays. A typical granular formation comprises the growth regulator compound dispersed on an inert carrier such as coarsely ground clay, or clay which has been converted to granules by treatment of a rolling bed of the powdered material with a small amount of liquid in a granulating drum. In the usual process for preparing granular formulations, a solution of the active compound is sprayed on the granules while they are being agitated in a suitable mixing apparatus, after which the granules are dried with a current of air during continued agitation.

Number	Name	Date
2661350	Hiltman et al.	Dec 1953
2872450	Sasse et al.	Feb 1959
3410842	Allais et al.	Nov 1968
3481951	Boroschewski et al.	Dec 1969

Number	Date	Country
1174103	Sep 1962	DEX
50-121175	Sep 1975	JPX
51-14885	May 1976	JPX
53-74549	Jul 1978	JPX
1272920	May 1972	GBX

Isothioureido isoindolediones and use as plant growth regulators

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Entry
E. Hoggarth, 1949, J. Chem. Soc., 198-223.
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Meran, Gh. Rev. Stiintifica, "V. Adamachi", 32, 136-138 (1946).
N. Buer Hoi et al., Bull Soc. Chim. France, 1956, 363-369.
P. Pel'kis et al., Zh. Obsch. Khim. 31, 3726-3728 (1961).