WO1992003440A1 - Herbicidal ethers - Google Patents

Abstract

Novel oxabicycloalkane ether derivative compounds of formulas (I-V) are disclosed, together with compositions containing these compounds and their methods of use. These compounds are biologically active as herbicides both post and preemergent with selectivity to a variety of crops.

Description

TITLE

HERBICIDAL ETHERS CROSS-REFERENCE TO RELATED APPLICATION

This application is a continuation-in-part of U.S.S.N. 07/568,487, filed August 16, 1990.

BACKGROUND OF THE INVENTION

Field of the Invention

The present invention relates to novel oxabicycloalkane ether derivative compounds, to compositions containing these ether derivative compounds, and to methods of using these compounds or compositions to control the growth of undesired vegetation particularly in rice.

Description of the Prior Art

Payne et al., U.S. Patent 4,567,283 and Payne et al., U.S. Patent 4,670,041 disclose a variety of herbicidal bicyclic ethers of the formula

DE 2937645 genetically discloses ethers as herbicides including oxabicyclo[3.3.1]nonane ethers.

U.S. 4,388,104 discloses ethers as herbicides including

dioxabicyclo[3.3. l]nonane ethers.

SUMMARY OF THE INVENTION

This invention pertains to compounds of Formulas I, II, III, IV and V including stereoisomers, suitable agricultural compositions containing them and their use as broad spectrum preemergent and postemergent herbicides:

wherein

X is OR⁵, SR⁵, C₁-C₆ acyloxy, benzoyloxy, halogen, N(R⁶)R⁷,

N(R⁶)O^R7;

R¹ is H or straight chain C₁-C₃ alkyl optionally substituted with 1 or more deuteriums;

R² is H or C₁-C₄ alkyl;

R³ is H, C₁-C₃ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₃ alkyl substituted with OCH₃ or OCH₂CH₃, or may be taken together with R² to form a 5 or 6-membered spiro or fused ring; R⁴ is H, C₁-C₃ alkyl, C₂-C₄ alkenyl, C₁-C₆ acyl or benzoyl;

R⁵ is H, C₁-C₃ alkyl optionally substituted with 1 or more

deuteriums, hydroxyl, C₁-C₃ alkoxyls or halogens; C₂-C₄ alkenyl; C₃-C₄ alkynyl; or phenyl optionally substituted with 1-3 substituents selected from halogen, C₁-C₃ alkyl, C₁-C₃ alkoxyl, CN, C₁-C₃ haloalkyl, C₁-C₃ haloalkoxyl, C₁-C₃ alkylthio, C₂-C₄ alkenyl, C₁-C₄ alkynyl or NO₂;

R⁶ and R⁷ are independently H, C₁-C₃ alkyl or may be taken

together to form a 5- or 6-membered saturated or unsaturated heterocyclic ring containing 1-4 nitrogens, 0-1 oxygen or 0-1 sulfur, each ring optionally substituted with 1-2 substituents selected from halogen, CH₃ or OCH₃, such as but not limited to pyrrole, pyrazole, imidazole, tetrazole, triazole, pyrrolidine, piperidine, morpholine, piperazine, thiazolidine, isoxazolidine, oxazolidine or tetrahydrooxazine;

Q is -CH₂W or

R⁸ is H, halogen, C₁-C₃ alkyl, OR⁹, SR⁹ or CN;

R⁹ is C₁-C₃ alkyl or C₁-C₃ haloalkyl;

J is CH₂, NR¹⁰, O, S or may be taken to form a double bond with an adjacent carbon;

R¹⁰ is H or C₁-C₃ alkyl;

q¹ is 0-2;

q² is 0-2; and

W is phenyl optionally substituted with 1-3 substituents selected from halogen, C₁-C₃ alkyl, C₁-C₃ alkoxyl, OH, CN, C₁-C₃ haloalkyl, C₁-C₃ haloalkoxyl, C₁-C₃ alkylthio, C₂-C₄ alkenyl or C₂-C₄ alkynyl, or W is a 5-, 6- or 7-membered heterocyclic ring containing 0-2 nitrogens, 0-2 oxygens or 0-2 sulfurs, each ring optionally substituted with 1-2 substituents selected from halogen, CH₃ or OCH₃; a representative exemplification of such heterocycles includes but is not limited to pyrrole, furan, thiophene, tetrahydrofuran, tetrahydropyran, isoxazole, oxazole, pyrazole, imidazole, thiazole, pyridine and pyrazines; provided that

1) the sum of q¹ and q² is 0-2 and

2) if the sum of q¹ and q² is 0 then J is CH₂.

The term "halogen", either alone or in compound words such as "haloalkyl", denotes fluorine, chlorine or bromine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different.

Examples of haloalkyl include CH₂CH₂F, CF₂CF₃ and CH₂CHFCI.

In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl", denotes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl or isopropyl.

Preferred for either their biological activity or ease of synthesis are:

1) Compounds of Formulas I, II, III, IV and V wherein:

W is phenyl optionally substituted by 1-2 substituents selected from halogen, CH₃ or OCH₃; or W is

tetrahydropyran, tetrahydrofuran, thiophene, thiazole, isoxazole, pyridine or pyrazine, each ring optionally substituted with 1-2 substituents selected from F, Cl, Br, CH₃ or OCH₃;

Q is

2. Compounds of Preferred 1 wherein:

R¹ is straight chain C₁-C₃ alkyl optionally substituted with

1 or more deuteriums;

R³ is H, C₁-C₃ alkyl or may be taken with R² to form a 5- or

6-membered spiro ring;

R⁴ is C1-C3 alkyl, C₁-C₆ acyl or benzoyl;

R⁸ is H, CH₃, halogen, OCH₃ or SCH₃.

3. Compounds of Preferred 2 wherein

X is OR⁵, SR⁵, C₁-C₆ acyloxy, benzoyloxy or

N(R⁶)R⁷.

4. Compounds of Preferred 3 wherein

R⁵ is H; C₁-C₃ alkyl optionally containing 1 or more

deuteriums or C₁-C₃ alkoxyls; or phenyl optionally substituted with 1-2 substituents selected from halogen, CH₃ or OCH₃.

5. Compounds of Preferred 4 wherein Q is Q-1, Q-3, Q-6, Q-7 or

Q-15.

6. Compounds of Preferred 5 wherein the compound is a

compound of Formula I.

7. Compounds of Preferred 5 wherein the compound is a

compound of Formula II.

8. Compounds of Preferred 5 wherein the compound is a

compound of Formula IH.

9. Compounds of Preferred 5 wherein the compound is a

compound of Formula IV.

10. Compounds of Preferred 5 wherein the compound is a

compound of Formula V.

Specifically Preferred for their biological activity and/or ease of synthesis are the compound of Preferred 10 which are: 5-(methoxy-d3)-1-methyl-2-(phenylmethoxy)-9- oxabicyclo[3.3.1]nonane, exo-:

5-methoxy-1-methyl-2-(phenylmethoxy)-9-oxabicyclo- [3.3.1]nonane, exo-;

1-ethyl-5-methoxy-2-(phenylmethoxy)-9-oxabicyclo- [3.3.1]nonane, exo-; and

2-[(2-fluorophenyl)methoxy]-5-methoxy-1-methyl-9- oxabicyclo[3.300]nonane. exo-.

Agriculturally suitable compositions for controlling the growth of undesired vegetation according to the invention are also disclosed. These compositions comprise an effective amount of the compounds recited herein and at least one of the following: surfactant, solid diluent or liquid diluent.

Methods for controlling the growth of undesired vegetation according to the invention are also disclosed. These methods comprise applying to the locus to be protected an effective amount of the

compounds recited herein.

DETAILED DESCRIPTION OF THE INVENTION

The compounds of Formula I, II, IH, IV and V exhibit geometrical and optical isomerism and can be prepared in geometrically or optically pure or mixed forms. The various individual optical and geometrical forms and various combinations thereof of the materials of the invention usually have some difference in herbicidal properties. Generally preferred for herbicidal activity are those geometrical isomers of

Formulas I, II and V wherein the OQ group bears a syn relationship to the -O- bridge (i.e., the OQ group resides in the exo orientation on the same face of the carbocyclic ring as the -O- bridge), and those geometrical isomers of Formulas III and IV wherein the OQ group bears a syn

relationship to the -C(R²)(R³)-O- bridge (i.e., the OQ group resides in the endo orientation on the same face of the carbocyclic ring as the -

C(R²)(R³)-O- bridge. The present invention contemplates all herbicidally active forms resulting from synthesis and from deliberately created mixtures, including those from among the synthetic intermediates and precursors which demonstrate herbicidal activity.

Compounds of Formula I can be made as depicted in Scheme 1

(page 22). The precursors of Formula 1 are commercially available or can be prepared easily by those skilled in the art of organic synthesis. A dissolving metal reduction of the compound of Formula 1, using for example lithium in liquid ammonia (see for example H.O. House, Modern Synthetic Reactions. 2nd Ed. W.A.Benjamin, Menlo Park, CA (1972), pp 190-209.), followed by hydrolysis of the resulting substituted

methoxycyclohexadiene with a weak acid such as oxalic acid will generate the compound of Formula 2, the corresponding 4-substituted cyclohex-3-en-1-one.

The enone of Formula 2 can be acetalized by the following treatment: heating, in the presence of an acid such as 2-naphthalenesulfonic acid, under conditions of water removal from the reaction system such as with a Dean-Stark trap, with an alcoholic reagent of the form AOH where the A group can be C₁-C₄ alkyl or two A can be taken together to form a C₂-C₆ diol such as ethylene glycol (for acetaHzations, see F. A. J. Meskens, Synthesis 501 (1981).

The intermediate acetal can be converted to the acetal diol of Formula 3 by treatment with catalytic osmium tetroxide in the presence of a stoichiometric oxidant such as N-methylmorpholine-N-oxide or trimethylamine oxide, in a suitable solvent system such as water/tert-butyl alcohol/pyridine (see for example R. Ray & D. S. Matteson,

Tetrahedron Lett. 21449 (1980)). This oxidation of the intermediate acetal to the acetal diol of Formula 3 can also be effected with potassium permanganate or other similar oxidative reagents. The acetal diol of Formula 3 can be selectively coupled with an alkylating agent QY, where Y is a leaving group, in the presence of a base such as sodium hydride in a solvent such as a mixture of tetrahydrofuran and dimethylacetamide, to yield the acetal glycol monoether of Formula 4

(for general examples of this ether synthesis, see N. Baggett in

Comprehensive Organic Chemistry, D. Barton & W. D. Ollis, eds., Vol. 1.

Pergamon Press, New York (1979) pp 819-832). Typical leaving groups are exemplified by but not limited to Cl, Br, I, and GSO₃, where the group G of the organosulfonate moiety is exemplified by but not limited to CH₃, CF₃, phenyl and p-methylphenyl. It is well known in the art that a selective ether coupling is possible at a secondary hydroxyl in preference to a tertiary hydroxyl.

The acetal glycol monoether of Formula 4 can undergo internal acetal exchange in the presence of a catalytic quantity of an anhydrous acid such as 2-naphthalenesulfonic acid to yield the substituted

oxabicycloheptanol ether of Formula I (X = OA).

The substituted oxabicycloheptanol ether of Formula I (X = OA) can be hydrolyzed in aqueous acid to give the hydroxyl-substituted oxabicycloheptanol ether of Formula I (X = OH).

An alternative synthesis of the 4-substituted cyclohex-3-en-l-one of Formula 2 is described in Scheme 2 (page 23). The commercially

available cyclohexan-1,4-dione of Formula 5 can be reacted with an organometallic reagent of the type R¹M where the metallic group M is exemplified by but not limited to Ii, MgBr, 1/2 Mg, MgCl, Mgl, ZnBr, 1/2 Zn, ZnCl and Znl. The product of this reaction can be represented by the 4-substituted-l-hydroxyoxabicyclo[2.2.1]heptane of Formula 6, and this can be subjected to a dehydration reaction in the presence of an acid such as 2-naphthalenesulfonic acid under conditions of water removal, such as with a Dean-Stark trap, to furnish the enone of Formula 2. Compounds of Formula I with various X groups can be

interconverted as exemplified by but not limited to the reactions depicted in Scheme 3.

Thus the compound of Formula I (X = OA) can undergo exchange with a reagent R⁵ZH, where R⁵ as previously defined and Z is oxygen or sulfur, in the presence of an acid such as 2-naphthalene-sulfonic acid to give Formula I (X = ZR⁵).

Likewise the compound of Formula I (X = OH) can undergo exchange with a reagent R⁵ZH in the presence of an acid to give Formula

I (X = ZR⁵).

Formula I (X = OA) can undergo exchange with an amine

HN(R⁶)R⁷ in the presence of an acid to give Formula I (X = N(R⁶)R⁷).

Formula I (X = OA) can undergo exchange with a hydroxylamine ether R⁶NHOR⁷ in the presence of an acid to give Formula I (X =

N(R⁶)OR⁷).

Formula I (X = OH) can undergo halogen exchange under the influence of a halogen exchange agent, such as thionyl chloride, to give

Formula I (X = Cl). Other halogen agents are exemplified by but not limited to thionyl bromide, phosphorus trichloride, phosphorus

pentachloride or phosphorus tribromide. Formula I (X=OH) can also undergo sulfonation by the action of organic sulfonyl chlorides (for example p-toluenesulfonyl chloride) in the presence of a base such as pyridine to give rise to the sulfonate of Formula I (X = GSO₃).

Formula I (X = Y) where Y is a leaving group as described above can be converted to Formula I (X = ZR⁵) by the action of R⁵ZH in the presence of a base such as sodium hydride.

Formula I (X = OH) can be converted to Formula I (X = OA¹) by treatment with A¹Y, where A¹ can be certain of the groups within the scope of R⁵ (e.g., C₁-C₆ akyloxy, benzoyloxy) in the presence of a base such as sodium hydride. The compounds of Formula II can be prepared from the

intermediate of Formula 3 as shown in Scheme 4 (page 24). Selective sulfonylation of the diol acetal of Formula 3 with an organic sulfonyl chloride GSO₂CI in the presence of a base such as pyridine will take place at the least hindered hydroxyl group to give the diol monosulfonate of Formula 7. Internal acetal exchange in the compound of Formula 7 in the presence of anhydrous acid such as 2-naphthalenesulfonic acid will lead to a substituted oxabicycloheptane derivative, and the action of a base such as potassium tert-butoxide will cause elimination of the sulfonate group to furnish the substituted unsaturated oxabicycloheptane of Formula 8. Hydrolysis of the compound of Formula 8 gives rise to the corresponding hydroxyl-substituted compound of Formula 9. A syn hydroxylation of the double bond of the compound of Formula 9 with catalytic osmium tetroxide in the presence of a stoichiometric oxidant such as a tertiary amine oxide (as described earlier in the conversion of the compound of Formula 2 to the compound of Formula 3 in Scheme 1) will produce the triol compound of Formula 10.

The ether coupling of the compound of Formula 10 with an alkylating agent QY in the presence of a base such as sodium hydride will likely show selectivity for the formation of the triol monoether compound of Formula 11 based on projected solvation sphere

requirements for the triol functional group. If necessary, this selectivity could be increased by carrying out the ether coupling on an analog of the compound of Formula 10 in which the bridgehead hydroxyl is capped with a bulky group such as dimethyl-tert-butylsilyl, by methods known to the art. A second stage of ether coupling performed on the compound of Formula 11 with an alkylating or acylating agent R⁴Y, for example methyl iodide, should occur at the least hindered of the two remaining hydroxyl groups to yield the compound of Formula II (cis, X = OH).

The diol of Formula 11 can be oxidized, for example with

dimethylsulfoxide and oxalyl chloride (see for example A. J. Mancuso & D. Swern, Synthesis 165 (1981)), to produce the keto compound of Formula 12. It is well known in the art that such bicyclic ketones undergo highly selective reduction with hindered hydride reagents, such as lithium tri-sec-butylborohydride, to give rise to an endo alcohol. This reaction will serve to convert the keto compound of Formula 12 to the trans diol of Formula 13. A final ether coupling of the diol of Formula 13 with an alkylating or acylating agent R⁴Y, for example benzoyl chloride, to yield the compound of Formula II (trans, X = OH). The various compounds of Formula II differing in the identity of X can be prepared and interconverted as shown for the compounds of Formula I in Scheme 3.

The compounds of Formula III can be prepared as shown in

Scheme 5 (page 25). Diels-Alder reactions such as that between the compound of Formula 14 and the compound of Formula 15 are well known in the art. The orientation of the addition, i.e. whether the product is the compound of Formula 16 or the compound of Formula 20 in Scheme 6, can be controlled by the identity of the group E in the precursor of Formula 14, and by the judicious choice of reaction

conditions such as solvent, temperature and the use of catalysts. The group E can be alkyl of the R³ type, alkoxyl of the OR³ type, or a salt of the O-M⁺ type.

The group E in the compound of Formula 16 can be converted to the R³ group in the compound of Formula 17 by straightforward methods known to the art. The transformation of compound of Formula 17 to the intermediate compound of Formula 18 follows the two-step process used for the conversion of the compound of Formula 2 to the compound of Formula 3 in Scheme 1. Likewise, the last two steps of ether coupling (Formula 18 ® Formula 19) and hydrolysis (Formula 19 ® Formula III (X = OH)) also parallel those shown in Scheme 1. The various compounds of Formula III differing in the identity of X can be prepared and

interconverted as shown for the compounds of Formula I in Scheme 3. The synthesis of the compounds of Formula IV is shown in Scheme

6, and follows very closely the preparation of compounds of Formula III shown in Scheme 5. The difference is in the orientation of the Diels- Alder addition, which (as described above) can be controlled by the proper choice of the group E and by the reaction conditions. The various compounds of Formula IV diflFering in the identity of X can be prepared and interconverted as shown for the compounds of Formula I in Scheme 3.

The synthesis of the compounds of Formula V is shown in Scheme

7. Starting with the commercially available cyclooctan-1,5-diol (Formula 24), a two-step process serves to produce the intermediate of Formula 25: firstly an oxidation of the diol of Formula 24 to a diketone intermediate using for example the dimethylsulfoxide/oxalyl chloride oxidant; secondly the addition of an organometallic R^M such as ethyl magnesium bromide. The compound of Formula 25 is subjected to dehydration in the presence of acid (for example 2-naphthalenesulfonic acid) under conditions of water removal, such as using a Dean-Stark trap. The intermediate produced is then subjected to acetalization conditions with a hydroxylic reagent AOH in the presence of acid under conditions of water removal, to furnish the compound of Formula 26. The double bond of the

compound of Formula 26 is then hydroxylated to produce the diol compound of Formula 27 in an analogous fashion to the conversion of the compound of Formula 9 to the compound of Formula 10 in Scheme 4. The resulting diol of Formula 27 undergoes a selective ether coupling reaction resulting in the glycol monoether compound of Formula 28, as described above for the conversion of the compound of Formula 3 to the compound of Formula 4 in Scheme 1. The glycol compound of Formula 28 can be hydrolyzed in aqueous acid to produce the compound of Formula V (X = OH). The various compounds of Formula V differing in the identity of the group X can be prepared and interconverted as described for the

compounds of Formula I in Scheme 3. The following examples illustrate preparation of the compounds of this invention.

Example 1

exo-1-methyl-2-(phenylmethoxy)-9-oxabicyclo[3.3.1]non an-5-o :

Step A Cyclooctan-1.5-dione (from S.L. Schreiber et al, J. Org. Chem. 54

5994 (1989))

A solution of 28 mL of oxalyl chloride (0.321 mol) in 500 mL of methylene chloride in a flame-dried 2L four-neck flask equipped with a thermometer, mechanical stirrer, septum and N2 inlet was chilled to

-70°C and charged with 44 mL of dimethylsulfoxide (0.617 mol). After 10 m a solution of 20.025 g of cis-cyclooctan-1,5-diol (0.139 mol) in

160 mL of methylene chloride and 40 mL of dimethylsulfoxide was added while maintaining the temperature < -70°C. The resulting mixture was stirred at approximately -75°C for 1 h, and was then charged dropwise with 193 mL of triethylamine (1.38 mol), and this mixture was stirred at approximately -75°C for 1 h and then warmed to room temperature over

2 1/2 h.

The reaction mixture was poured into 500 mL of water, the layers were separated and the aqueous layer was extracted with twice with methylene chloride. The combined organics were extracted once with brine, dried (Na2Sθ4) and concentrated to give 30.83 g of a moist orange solid.

This was chromatographed on 553 g of silica gel with 20% acetone/petroleum ether, increasing to 30, 35, 40% acetone to yield 17.85 g of a yellow-white solid (92%): ¹H-NMR (CDCI₃) δ 2.2 (m, 4H); 2.5 (m, 8H).

Step B: 5-Methyl-9-oxabicyclo[3.3.1]nonan-1-ol (after A. Streitwieser Jr. et al, J. Org. Chem. 542331 (1989))

A flame-dried four-neck 1 L flask equipped with thermometer, N2 inlet, stopper and septum was charged with 300 mL of tetrahydrofuran (THF) followed by 176 mL of 1.4 M methyllithium in ether (0.246 mol), and this was cooled to approximately -76°C. A solution of 25.003 g of cyclooctan-1,5-dione (0.176 mol) in a total of 100 mL of THF was added via cannula, maintaining the temperature at approximately -70°C. The resulting mixture was stirred at approximately -70°C for 15 m and then warmed to room temperature over 2 h.

The reaction mixture was poured into 2:1 10% HCl/ice and this was extracted three times with ether. The combined organics were washed twice with brine, dried (MgSO₄) and concentrated to give 26.54 g of a beige solid.

This was chromatographed on 550 g of silica gel with 10%

acetone/petroleum ether, increasing the acetone to 15% and 20%, to yield 18.189 g of 5-methyl-9-oxabicyclo[3.3.1]nonan-l-ol as a white solid (66%): mp 65-70°C; ¹H-NMR (CDCl₃) δ 1.20 (s, 3H); 1.3-2.3 (m, 12H); 2.85 (s, 1H).

Step C: 5-Methylcyclooct-4-en-1-one (after A. Streitwieser Jr. et al, J. Org.

Chem. 54 2331 (1989))

A solution of 14.621 g of 5-methyl-9-oxabicyclo[3.3.1]nonan-1-ol

(0.0936 mol) in 350 mL of benzene was charged with 1.15 g of

2-naphthalenesulfonic acid and the resulting mixture was heated to reflux through a Dean-Stark trap. After 24 h of reflux, 1.8 mL (0.1 mol) of water had collected, so the heating was stopped.

The reaction mixture was worked up in saturated NaHC03(aq) and this was extracted twice with ether. The combined organics were extracted with brine, dried (MgSO₄) and concentrated to give 12.543 g of

5-methylcyclooct-4-en-1-one as an orange oil (97%): ¹H-NMR δ (CDCI₃) 1.5-1.8 (m, 2H); 1.70 (s, 3H); 2.0-2.7 (m, 8H); 5.47 (t, 1H, J = 7.5 Hz).

Step D: 8-Methyl-1 ,4-dioxaspiror4.71dodec-7-ene

A solution of 2.547 g of 5-methylcyclooct-4-en-1-one (18.3 mmol) in

80 mL of benzene was charged with 10 mL of ethylene glycol and 170 mg of 2-naphthalenesulfonic acid, and the resulting mixture was heated to reflux through a Dean-Stark trap, for 5 h.

The reaction mixture was cooled and worked up with saturated

NaHC03(aq), and this was extracted twice with ether. The combined organics were dried (MgS04) and concentrated to give 3.185 g of a murky yellow oil.

Chromatography on 81 g of silica gel using 3% acetone in petroleum ether, increasing to 6%, yielded 2.77 g of 8-methyl-l,4- dioxaspiro[4.7]dodec-7-ene (82%): ¹H-NMR δ (CDCI₃) 1.5-2.0 (m, 9H);

1.68 (s, 3H); 2.0-2.5 (m, 4H); 3.94 (s, 4H); 5.52 (t, 1H, J = 7.5 Hz).

Step E: cis-8-Methyl-1,4-dioxaspiro[4.7]dodeca-7.8-diol (after Matteson,

Tetrahedron Lett. 21 449 (1980))

In a 1 L four-neck flask, equipped with mechanical stirrer, thermometer, reflux condenser (N2 inlet) and stopper, was prepared a solution of 13.144 g of 8-methyl-1,4-dioxaspiro[4.7]dodec-7-ene (72.1 mmol), 11.36 g of trimethylamine oxide dihydrate (102 mmol) and 45 mg of osmium tetroxide (0.177 mmol) in a mixture of 225 m L of tert-butanol.

75 mL of water and 6 mL of pyridine. The resulting mixture was heated to reflux for 17 h, at which time the heating mantle was removed.

The reaction mixture was charged with 250 mL of 20% NaHSθ3

(aq) and stirred for several hours. The reaction mixture was diluted with 250 mL of water, and was extracted with 100 mL of ether and then twice with 100 mL of methylene chloride. The combined organics were extracted with 250 mL of brine, dried (MgSO₄) and concentrated to give

19.918 g of a yellowish liquid which partially solidified overnight.

This was chromatographed on 800 g of silica using 10% acetone in petroleum ether, increasing to 15%, 25%, 40%, 65% and 80% acetone, to yield 10.638 g (68%) of as-8-methyl-1,4-dioxaspiro[4.7]dodeca-7,8-diol as a white solid: mp 76-79°C; ¹H-NMR (CDC1₃) δ 1.27 (s, 3H); 1.3-2.3 (m,

10H); 2.60 (br s, 1H); 2.85 (br s, 1H); 3.65 (br t, 1H); 3.92 (s, 4H).

Step F: cis-8-Methyl-7-(phenylmethoxy)-1,4-dioxaspiro-[4.7]dodecan-8-ol A suspension of 2.579 g of 80% NaH (in mineral oil) (86 mmol) was suspended in 50 mL of THF and this was charged with a solution of 5.001 g of cis-8-methyl-1.4-dioxaspiro[4.7]dodeca-7,8-diol in a total of

18 mL of THF, and this was diluted with 30 mL of dimethylacetamide (DMAC). The reaction mixture was placed under an N₂ atmosphere and cooled in a cool water bath during the addition of 2.82 mL of benzyl bromide (23.7 mmol). The resulting mixture was allowed to stir at room temperature for 1 1/2 days.

The reaction mixture was poured into 250 mL of saturated

NH4Cl(aq), and this was extracted with three 50 mL portions of ether. The combined organics were dried (MgSO₄) and concentrated to give 8.053 g of an orange liquid.

The crude product was chromatographed on 350 g of silica using 5% acetone in petroleum ether (increasing to 10%, 15%, 20% and 25%) to yield 214 mg (2%) of a yellowish liquid identified by ¹H-NMR as the bis- benzylated product, and 6.602 g (95%) of cis-8-methyl-7-(phenylmethoxy)- 1,4-dioxaspiro[4.7]dodecan-8-ol as a light yellow liquid: ¹H-NMR

(CDCI₃) δ 1.22 (s, 3H); 1.3-2.3 (m, 10H); 2.78 (s, 1H); 3.37 (br d, 1H, J =

7.5 Hz); 3.87 (s, 4H); 4.35 (d, 1H, J = 12.5 Hz); 4.65 (d, 1H, J = 12.5 Hz);

7.35 (s, 5H).

Step G:exo-1-methyl-2-(phenylmethoxy)-9-oxabicyclo-[3.3.1]nonan-5-ol

A solution of 6.248 g of cis-9-methyl-8-(phenylmethoxy)-1,4-dioxaspiro[[4.7]dodecan-9-ol (20.4 mmol) in a mixture of 75 mL of acetone and 75 mL of water was charged with 15 mL of cone H₂SO₄, and was heated to reflux for 19 1/2 h. The reaction mixture was poured into 250 mL of water, and this was extracted with three 35 mL portions of methylene chloride. The combined organics were extracted with 75 mL of brine, and were dried and concentrated to give 6.421 g of a tan solid.

This was chromatographed on 200 g of silica using 10% acetone in petroleum ether (increasing to 20% and 30%) to yield 5.366 g of a pale yellow solid. ^H-NMR indicated the hydrolysis to be incomplete, so this product was resubjected to the above reaction conditions for an additional 20 h, and was worked up and purified as above, to yield 3.977 g (74%) of exo-l-methyl-2-(phenvlmethoxy)-9-oxabicyclor3.3. l]nonan-5-ol as a tan solid: mp 59-67°C; ¹H-NMR (CDC1₃) δ 1.30 (s, 3H); 1.2-2.2 (m, 10H);

3.01 (t, 1H, J = 2.5 Hz); 3.55 (br s, 1H); 4.37 (d, 1H, J = 12 Hz); 4.62 (d, 1H, J = 12 Hz); 7.33 (s, 5H).

Example 2

exo-5-Methoxy-1-methyl-2-(phenylmethoxy)-9-oxabicy-clo[3.3,1]]nonane

A solution of 192 mg of exo-1-methyl-2-(phenylmethoxy)-9-oxa-bicyclo[3.3.1]nonan-5-ol (0.690 mmol) in 5 mL of methanol was charged with 20 drops of cone H₂SO₄ and the resulting mixture was heated to reflux for 8 h and then stood at room temperature for 16 h.

The reaction mixture was poured into 60 m L of saturated

NaHCO₃(aq), and this was extracted three times with 15 mL of ether.

The combined organics were extracted with 50 mL of brine, dried

(MgS04) and concentrated to give 176 mg of a yellow oil.

The crude product was chromatographed on 4 g of silica gel using

2.5 % acetone in petroleum ether to yield 160 mg (79%) of exo-5-methoxy-1-methyl-2-(phenylmethoxy)-9-oxabicyclo[3.3.1]nonane as a pale yellow oil: ¹H-NMR (CDCI₃) δ 1.28 (s, 3H); 1.2-2.2 (m, 10H); 3.00 (t, 1H, J = 3

Hz); 3.32 (s, 3H); 4.38 (d, 1H, J = 12 Hz); 4.63 (d, 1H, J = 12 Hz); 7.28 (s, 5H). Example 3

exo-5-Chloro-1-methyl-2-(phenylmethoxy)-9- oxabicyclo[3.3.1]nonane (after C.B. Quinn, Ph.D. Dissertation (Univ. Michigan, 1973))

A solution of 602 mg (2.29 mmol) of cis-1-methyl-2-(phenylmethoxy)-9-oxabicyclo[3.3.1]nonan-5-ol in 10 mL of benzene was charged with 3.2 mL of triethylamine (23.3 mmol), and then chilled in an ice/water bath and charged dropwise with 0.34 mL of SOCl₂. The resulting mixture was warmed to room temperature over 3 1/2 h.

The reaction mixture was poured into 50 mL of saturated

NH₄Cl(aq) and this was extracted with three 20 mL portions of ether.

The combined organics were extracted with 50 mL of brine, dried

(MgS04) and concentrated to give 864 mg of black-red oil.

The crude product was chromatographed on 45 g of silica with 5% acetone in petroleum ether (increasing to 10% and 20%) to yield 512 mg (80%) of exo-5-chloro-1-methyl-2-(phenylmethoxy)-9-oxabicyclo-[3.3.1]nonane as a dark red-brown oil: ¹H-NMR (CDCI₃) δ 1.30 (s, 3H);

1.1-2.4 (m, 10H); 3.03 (br s, 1H); 4.38 (d, 1H, J = 12 Hz); 4.60 (d, 1H, J = 12 Hz); 7.36 (s, 5H).

Example 4

exo-2-[(2-Fluorophenyl)methoxyl-5-methoxy-1-methyl-9- oxabicyclo[3.3. 1]nonane

Step A: cis-8-Methyl-7-[(2-fluorophenyl)methoxy]-1,4-dioxaspiro[4,7]- dodecan-8-ol

A suspension of 232 mg of NaH (80% in mineral oil) (7.73 mmol) in 3 mL of THF was charged with a solution of 451 mg of cis-8-methyl-1.4-dioxaspiro-[4.7]dodeca-7,8-diol (1.94 mmol) in a total of 6.5 mL of THF, and this was diluted with 3 mL of DMAC and then charged with 0.266 mL of 2-fluorobenzyl bromide (2.13 mmol). The reaction mixture was stirred at room temperature for 1 1/2 d.

The reaction mixture was poured into 50 mL of saturated

NH₄Cl(aq), and this was extracted three times with 20 mL of ether. The combined organics were extracted with 50 mL of brine, dried (MgSO₄) and concentrated to give 664 mg of an orange-yellow liquid.

The crude product was chromatographed on 35 g of silica using 5% acetone in petroleum ether (increasing to 10%) to yield 529 mg (80%) ofcis-8-methyl-7-[(2-fluorophenyl)methoxy]-1,4-dioxaspiro[4.7]dodecan-8-ol as a pale yellow liquid: ¹H-NMR (CDCI₃) δ 1.20 (s, 3H); 1.3-2.3 (m, 10H); 2.68 (s, 1H); 3.38 (br d, 1H, J = 7.5 Hz); 3.87 (s, 4H); 4.45 (d, 1H, J = 12 Hz); 4.65 (d, 1H, J = 12 Hz); 6.85-7.5 (m, 4H).

Step B: exo-2-[(2-Fluorophenyl)methoxy]-1-methyl-9-oxabicyclo[3.3.1]- nonan-5-ol

A solution of 529 mg of cis-8-methyl-7-[(2-fluorophenyl)methoxy]- 1,4-dioxaspiro[4.7]dodecan-8-ol (1.55 mmol) was taken up in a mixture of

10 mL of acetone and 10 mL of water, and this was charged with 4 mL of cone H2SO4, and the resulting mixture was heated to reflux for 4 h.

The reaction mixture was poured into 60 mL of water, and this was extracted with three 20 mL portions of methylene chloride. The

combined organics were extracted with 50 mL of saturated NaHCO₃(aq), dri ed (MgSO₄) and concentrated to give 659 mg of a pale yellow solid.

The crude product was purified by chromatography on 30 g of silica using 10% acetone in petroleum ether (increasing to 20%) to yield 459 mg (100%) of exo-2-[(2-fluorophenyl)methoxy]-1-methyl-9-oxabicyclo- [3.3.1]nonan-5-ol as a white solid: mp 95-101°C; ¹H-NMR (CDCI₃) δ 1.27

(finely split s, 3H); 1.3-2.2 (m, 10H); 2.66 (d, 1H, J = 10.6 Hz); 3.07 (t, 1H, J = 2.8 Hz); 4.51 (d, 1H, J = 12.1 Hz); 4.69 (d, 1H, J = 12.1 Hz); 7.0-7.5 (m, 4H). Step C: exo-2-[(2-Fluorophenyl)methoxy]-5-methoxy-1-methyl-9- oxabicyclo[3.3.1]nonane

A solution of 81 mg of exo-2-[(2-fluorophenyl)methoxy]-1-methyl-9-oxabicyclo[3.3.1]nonan-5-ol (0.272 mmol) in 5 mL of methanol was charged with 20 drops of cone H2SO4 and ihe resulting mixture was heated to reflux for 4 h and then stood overnight at room temperature.

The crude product was poured into 50 mL of saturated

NaHC03(aq) and this was extracted with three 15 mL portions of ether.

The combined organics were extracted with 50 mL of brine and were dried (MgSθ4) and concentrated to give 72 mg of a pale yellow oil.

Chromatography on 3.5 g of silica using 2.5% acetone in petroleum ether yielded 64 mg (75%) of exo-2-[(2-fluorophenyl)methoxy]-5-methoxy-1-methyl-9-oxabicyclo[3.3.1]nonane as a clear oil: ¹H-NMR (CDCI₃) δ 1.28 (s, 3H); 1.1-2.1 (m, 10H); 3.05 (t, 1H, J = 2.5 Hz); 3.35 (s, 3H); 4.47 (d, 1H, J = 12.5 Hz); 4.70 (d, 1H, J = 12.5 Hz); 6.8-7.6 (m, 4H).

A = C₁-C₄ alkyl; two A can be taken together to form a diol such as HO(CH₂)₂OH;

Y = leaving group such as Cl, Br, I, GSO₃.

G = CH₃, CF₃, Ph, p-CH₃Ph; and

R¹- and Q are as previously defined.

By the general procedures described or by obvious modifications thereof, the compounds of Tables 1-5 may be prepared.

TABLE 1

Formula I

R¹=H; X=OH; R¹=H; X=SCH₃; R¹=H; X=N(CH₃)₂; R¹=CH₃; X=OCH₃;

Q=CH₂W; W=W-1 Q=CH₂W; W=W-1 Q=CH₂W; W=W-1 Q=CH₂W; W=W-1

R¹² R¹³ R¹² R¹³ R¹² R¹³ R¹² R¹³

F H F H F H F H

F F F F F F F F

Cl H Cl H Cl H Cl H

Cl F Cl F Cl F Cl F

Cl Cl Cl Cl Cl Cl Cl Cl

Br H Br H Br H Br H

CN H CN H CN H CN H

CH₃ H CH₃ H CH₃ H CH₃ H

CH₂CH₃ H CH₂CH_Σ | H CH₂CH₃ H CH₂CH₃ H

OCH₃ H OCH₃ H OCH₃ H OCH₃ H

SCH₃ H SCH₃ H SCH₃ H SCH₃ H

FCH₂ H FCH₂ H FCH₂ H FCH₂ H

F₂CH H F₂CH H F₂CH H F₂CH H

F₃C H F₃C H F₃C H F₃C H

F₂CHO H F₂CHO H F₂CHO H F₂CHO H

F₃CO H F₃CO H F₃CO H F₃CO H

CH=CH₂ H CH=CH₂ H CH=CH₂ H CH=CH₂ H

C≡CH H C≡CH H C≡CH H C≡CH H

Formula I R¹=CH₃; R¹=CH₃; R¹=CH₂CH₃; R¹=CH₂CH₃;

X=O₂CCH₃; X=NCH₃OCH₃; X=OH; X=SCH₃;

Q=CH₂W; W=W-1 Q=CH₂W; W=W-1 Q=CH₂W; W=W-1 Q=CH₂W; W=W-1

R¹² R¹³ R¹² R¹³ R¹² R¹³ R¹² R¹³

F H F H F H F H

F F F F F F F F

Cl H Cl H Cl H Cl H

Cl F Cl F Cl F Cl F

Cl Cl Cl Cl Cl Cl Cl Cl

Br H Br H Br H Br H

CN H CN H CN H CN H

CH₃ H CH₃ H CH₃ H CH₃ H

CH₂CH₃ H CH₂CH₃ H CH₂CH₃ H CH₂CH₃ H

OCH₃ H OCH₃ H OCH₃ H OCH₃ H

SCH₃ H SCH₃ H SCH₃ H SCH₃ H

FCH₂ H FCH₂ H FCH₂ H FCH₂ H

F₂CH H F₂CH H F₂CH H F₂CH H

F₃C H F₃C H F₃C H F₃C H

F₂CHO H F₂CHO H F₂CHO H F₂CHO H

F₃CO H F₃CO H F₃CO H F₃CO H

CH=CH₂ H CH=CH₂ H CH=CH₂ H CH=CH₂ H

C≡CH H C≡CH H C≡CH H C≡CH H

Formula I R¹=CH₂CH₃;

X=N(CH₃)₂;

Q=CH₂W; W=W-1

R¹² R¹³

F H

F F

Cl H

Cl F

Cl Cl

Br H

CN H

CH₃ H

CH₂CH₃ H

OCH₃ H

SCH₃ H

FCH₂ H

F₂CH H

F₃C H

F₂CHO H

F₃CO H

CH=CH₂ H

C≡CH H

Formula I

R¹=M; X=OH; Q=CH₂W

V=O V=S R¹⁴=H

W R¹⁷ W R¹⁷ W R15

W-7 H W-7 H W-2 H W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula I

R¹=H; X=OH; Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V=S V=S V=S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹ ₇ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula I

R¹=H; X=OH;

Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃ CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷= CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula I

R¹=H; X=SCH₃; Q=CH₂W

V=O V=S R¹⁴=H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula I

R¹=H;X=SCH₃; Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃ CH₃ H CH₃ H CH₃ H CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V=O V= O V= O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F H CH₃ H CH₃ H CH₃

F H H F H

F F F F F F CH₃ CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula I

R¹=H;X=SCH₃

Q=CH₂W

W=W-13 W=W-14 W=W-16 R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17;R¹⁷=F W=W-18;V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1;R⁸=H Q=Q-7;R⁸=H

Q=Q-3;R⁸=H Q=Q-8;R⁸=H

Q=Q-5;R⁸=H Q=Q-15;R⁸=H

Q=Q-6;R⁸=H

Formula I

R¹=H; X=N(CH₃)₂; Q=CH₂W

V =O V=S R¹⁴=H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula I

R¹=H; X=N(CH₃)₂; Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V=O V =O V =O R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula I

R¹ =H; X=N(CH₃)₂

Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W-W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7 R⁸=H

Q=Q-3; R⁸=H Q=Q-8, R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula I

R¹=CH₃ X=OCH₃; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula I

R¹=CH₃; X=OCH₃; Q=CH₂W

W= W-11 W=W-12 W=W-15

V =O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V=S V=S V=S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula I

R¹=CH₃; X=OCH₃

Q=CH₂W

W=W-13 W=W-14 W=W-16 R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

QβQ-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula I

R¹=CH₃; X=O₂CCH₃; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula I

R¹=CH₃; X=O₂CCH₃; Q=CH₂W

W=W-11 W=W-12 W=W-15 V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V =S V=S V=S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula I

R¹=CH₃; X=O₂CCH₃

Q=CH₂ ^W

W=W-13 W=W-14 W=W-16 R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃ CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19 W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula I

R¹=CH₃;X=NCH₃OCH₃; Q=CH₂W

V= O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula I

R¹=CH₃; X=NCH₃OCH₃; Q=CH₂W

W=W-11 W=W-12 W=W-15 V=O V=O V =O R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V =S V=S V=S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula I

R¹=CH₃; X=NCH₃OCH₃

Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1 R⁸=H Q=Q-7; R⁸=H

Q=Q-3 R⁸=H Q=Q-8; R⁸=H

Q=Q-5, R⁸=H Q=Q-15; R⁸=H

Q=Q-6- R⁸=H

Formula I

R¹=CH₂CH₃; X=OH; Q=CH₂W

V=O V=S R¹⁴=H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ w-10 CH₃

Formula I

R¹=CH₂CH₃;X=OH; Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V =S V =S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula I

R¹=CH₂CH₃; X=OH

Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1 R⁸=H Q=Q-7; R⁸=H

Q=Q-3 R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula I

R^l=CH₂CH₃;X=SCH₃; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula I

R¹=CH₂CH₃; X=SCH₃; Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V= O V=O

R¹⁷ R¹⁸ R¹ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V =S V= S V= S

R¹⁷ R¹⁸ R¹ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula I

R¹= CH₂CH₃; X=SCH₃;

Q=CH₂W

W=W-13 W=W-14 W=W-16

_R17 _R18 R¹⁷ R¹⁸ R¹⁷ _R18

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula I

R¹=CH₂CH₃; X=N(CH₃)₂; Q=CH₂W

V= O V= S R¹⁴=H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula I

R¹=CH₂CH₃;X=N(CH₃)₂; Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula I

R¹=CH₂CH₃;X=N(CH₃)₂;

Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18;V=S

W=W-17;R¹⁷=CH₃ W=W-18;V=NCH₃

Q=Q-1; ;R⁸=H Q=Q-7;R⁸=H

Q=Q-3; R⁸=H Q=Q-8;R⁸=H

Q=Q-5; R⁸=H Q=Q-15;R⁸=H

Q=Q-6; R⁸=H

TABLE 2

Formula II R¹=H; X=OH; R¹=H; X=SCH₃; R¹=CH₃; X=OCH₃; R¹=CH₃; X=O₂CCH₃;

Q=CH₂W; Q=CH₂W; Q=CH₂W; Q=CH₂W;

R⁴=CH₃; W=W-1 R⁴=OCCH₃; W=W-1 R⁴=CH₃; W=W-1 R⁴=OCCH₃; W=W-1 R¹² R¹³ R¹² R¹³ R¹² R¹³ R¹² R¹³

F H F H F H F H

F F F F F F F F

Cl H Cl H Cl H ci H

Cl F Cl F Cl F Cl F

Cl Cl Cl Cl Cl Cl ci Cl

Br H Br H Br H Br H

CN H CN H CN H CN H

CH₃ H CH₃ H CH₃ H CH₃ H

CH₂CH₃ H CH₂CH_a | H CH₂CH₃ H CH₂CH₃ H

OCH₃ H OCH₃ H OCH₃ H OCH₃ H

SCH₃ H SCH₃ H SCH₃ H SCH₃ H

FCH₂ H FCH₂ H FCH₂ H FCH₂ H

F₂CH H F₂CH H F₂CH H F₂CH H

F₃C H F₃C H F₃C H F₃C H

F₂CHO H F₂CHO H F₂CHO H F₂CHO H

F₃CO H F₃CO H F₃CO H F₃CO H

CH=CH₂ H CH=CH₂ H CH=CH₂ H CH=CH₂ H

C≡CH H C≡CH H C≡CH H C≡CH H

R¹=CH₂CH₃; R¹=CH₂CH₃;

X=OH; Q=CH₂W; X=SCH₃; Q=CH₂W;

R⁴=CH₃; W=W-1 R⁴=OCCH₃; W=W-1 R¹² R¹³ R¹² R¹³

F H F H

F F F F

Cl H Cl H

Cl F Cl F

Cl Cl Cl Cl

Br H Br H

CN H CN H

CH₃ H CH₃ H

CH₂CH₃ H CH₂CH₃ H

OCH₃ H OCH₃ H

SCH₃ H SCH₃ H

FCH₂ H FCH₂ H

F₂CH H F₂CH H

F₃C H F₃C H

F₂CHO H F₂CHO H

F₃CO H F₃CO H

CH=CH₂ H CH=CH₂ H

C≡CH H C≡CH H

Formula II

R¹=H; X=OH; Q=CH₂W; R⁴=CH₃

V=O V= S R¹⁴=H

W R¹⁷ W R¹⁷ W R¹δ

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula II

R¹=H; X=OH; Q=CH₂W; R²=CH₃

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃ CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula II

R¹=H; X=OH; R⁴=CH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; Rⁱ⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1 ; R⁸=H Q=Q-7; R⁸=H

Q=Q-3 ; R⁸=H Q=Q-6 1; R⁸=H

Q=Q-5 ; R⁸=H Q=Q-15; R⁸=H

Q=Q-6 ; R⁸=H

Formula II

R¹=H; X=SCH₃; Q=CH₂W; R⁴=OCCH₃

V=O V= S R¹⁴=H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula II

R¹=H; X=SCH₃; Q=CH₂W; R⁴=0CCH₃

W=W-11 W=W-12 W=W-15

V=O V =O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃ CH₃ H CH₃ H CH₃ H CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula II

R¹=H; X=SCH₃; R⁴=OCCH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16 R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17 R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17: R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula II

R¹=CH₃; X=OCH₃; Q=CH₂W; R⁴=CH₃

V=O V= S R¹⁴=H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula II

R¹=CH₃; X=OCH₃; Q=CH₂W; R⁴=CH₃

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula II

R¹=CH₃; X=OCH₃; R⁴=CH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1 R⁸=H Q=Q-7; R⁸=H

Q=Q-3, R⁸=H Q=Q- 8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6 R⁸=H

Formula II

R¹=CH₃; X=O₂CCH₃; Q=CH₂W; R⁴=OCCH₃

V=O V= S R¹⁴=H

W R¹⁷ W R¹⁷ W R¹⁸

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F w-10 F

W-10 CH₃ w-10 CH₃

Formula II

R¹=CH₃; X=O₂CCH₃; Q=CH₂W; R⁴=OCCH₃

W=W -11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R^l8

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula II

R¹=CH₃; X=O₂CCH₃; R⁴=OCCH₃; Q=CH₂W

W= W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W-W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula II

R¹=CH₂CH₃; X=OH; Q=CH₂W; R⁴=CH₃

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W4 H

W-8 CH₃ W-8 CH₃ W4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula II

R¹=CH₂CH₃; X=OH; Q=CH₂W; R⁴=CH₃

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH3

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula II

R¹=CH₂CH₃; X=OH; R⁴=CH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18;V=S

W=W-17;R¹⁷=CH₃ W=W-18;V=NCH₃

Q=Q-1 ;R⁸=H Q=Q-7;R⁸=H

Q=Q-3 ;R⁸=H Q=Q-8; R⁸=H

Q=Q-5 ;R⁸=H Q=Q-15;R⁸=H

Q=Q-6 ;Rδ=H

Formula II

R¹=CH₂CH₃; X=SCH₃; Q=CH₂W; R⁴=OCCH₃

V=O V=S R¹⁴=H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula II

R¹=CH₂CH₃;X=SCH₃; Q=CH₂W; R⁴=OCCH₃

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula II

R¹=CH₂CH₃; X=SCH₃; R⁴=OCCH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ 18

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W--W-18; V=O W=W-19

W-W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; Rδ=H Q=Q-8; R⁸=H

Q=Q-5,; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

TABLE 3

Formula III

R¹ =H; X =OH; R¹=H; X=SCH₃; R¹=CH₃; X=OCH₃; R¹=CH₃; X=O₂CCH₃;

Q=CH₂W;R²=H; Q=CH₂W; R²=CH₃; Q=CH₂W; R²=CH₃; Q=CH₂W; R²=H;

R³=CH₃; W=W-1 R³=CH₂CH₃; W=W-1 R³=CH₃; W=W-1 R³=CH₂CH₃; W =W-1

R¹² R¹³ R¹² R¹³ R¹² R¹³ R¹² R¹³

F H F H F H F H

F F F F F F F F

Cl H Cl H Cl H Cl H

Cl F Cl F Cl F Cl F

Cl Cl Cl Cl Cl Cl Cl Cl

Br H Br H Br H Br H

CN H CN H CN H CN H

CH₃ H CH₃ H CH₃ H CH₃ H

CH₂CH₃ H CH₂CH₃ H CH₂CH₃ H CH₂CH₃ H

OCH₃ H OCH₃ H OCH₃ H OCH₃ H

SCH₃ H SCH₃ H SCH₃ H SCH₃ H

FCH₂ H FCH₂ H FCH₂ H FCH₂ H

F₂CH H F₂CH H F₂CH H F₂CH H

F₃C H F₃C H F₃C H F₃C H

F₂CHO H F₂CHO H F₂CHO H F₂CHO H

F₃CO H F₃CO H F3CO H F₃CO H

CH=CH₂ ^H CH=CH₂ H CH=CH₂ H CH=CH₂ H

C≡CH H C≡CH H C≡CH H C≡CH H

Formula III R¹=CH₂CH₃; R¹=CH₂CH₃;

X=OH; R²=CH₃; X=SCH₃; R²=H;

R³=CH₂CH₃; R³=CH₂CH₃;

Q=CH₂W ; W=W-1 W.W-1; Q=CH₂W

R¹² R¹³ R¹² R¹³

F H F H

F F F F

Cl H Cl H

Cl F Cl F

Cl Cl Cl Cl

Br H Br H

CN H CN H

CH₃ H CH₃ H

CH₂CH₃ H CH₂CH₃ H

OCH₃ H OCH₃ H

SCH₃ H SCH₃ H

FCH₂ H FCH₂ H

F₂CH H F₂CH H

F₃C H F₃C H

F₂CHO H F₂CHO H

F₃CO H F₃CO H

CH=CH₂ H CH=CH₂ H

C≡CH H C≡CH H

Formula III

R¹= H; X-OH; R²= H;

R3 =CH₃; Q=CH₂W

V=O V= S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula III

R¹=H; X=OH; Q=CH₂W

R²=H; R3=CH₃

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH3

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V =S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula III

R¹= H; X=OH; R²=H;;

R³ =CH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula III

R¹=H; X=SCH₃; R²=CH₃;

R³ =CH₂CH₃; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula IH

R¹=H;X=SCH₃; Q=CH₂W

R²=CH₃; R3=CH₂CH₃

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V=S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula III

R¹=H; X=SCH₃; R²=CH₃;

R³=CH₂CH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17;R¹⁷=H W=W-18;V=O W=W-19

W=W-17; R¹⁷=F W=W-18;V=S

W=W-17; R¹⁷=CH₃ W=W-18;V=NCH₃

Q=Q-1 ;R⁸=H Q=Q-7 ;R⁸=H

Q=Q-3;R⁸=H Q=Q-8 ;R⁸=H

Q=Q-5;R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula III

R¹=CH₃; X=OCH₃; R²=CH₃;

R³=CH₃; Q=CH₂W

V=O V=S R¹⁴=H

W R¹⁷ W R¹⁷ W R¹δ

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula III

R¹=CH₃; X=OCH₃; Q=CH₂W

R²-=CH₃; R3=CH₃

W=W-11 W=W-12 W=W-15 V=O V=O V=O R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula HI

R¹=CH₃; X=OCH₃; R²=CH₃;

R³=CH₃; Q=CH₂W

W=W-13 W= W-16 W=W-14

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18;V=S

W=W-17; R¹⁷=CH₃ W=W-18;V=NCH₃

Q=Q-1 ;R⁸=H Q=Q-7; R⁸=H

Q=Q-3 ;R⁸=H Q=Q-8; R⁸=H

Q=Q-5 ;R⁸=H Q=Q-15; R⁸=H

Q=Q-6 ;R⁸=H

Formula III

R¹=CH₃; X=O₂CCH₃; R²=H;

R³=CH₂CH₃; Q=CH₂W

V=O V= S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula III

R¹-=CH₃; X=O₂CCH₃; Q=CH₂W

R2_S-H; R³=CH₂CH₃

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula III

R¹=CH₃; X=O₂CCH₃; R²=H;

R³=CH₂CH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18;V=S

W=W-17; R¹⁷=CH₃ W=W-18;V=NCH₃

Q=Q-1;R⁸=H Q=Q-7 ;R⁸=H

Q=Q-3;R⁸=H Q=Q-8 ;R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula III

R¹=CH₂CH₃; X=OH; R²=CH₃;

R³=CH₂CH₃; Q=CH₂W

V=O V=S R^{1 4} =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula III

R¹=CH₂CH₃; X=OH; Q=CH₂W

R²=CH₃; R³=CH₂CH₃

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula III

R¹=CH₂CH₃; X=OH₃; R²=CH₃;

R³=CH₂CH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7 ; R⁸=H

Q=Q-3; R⁸=H Q=Q-8 ; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula III

R¹=CH₂CH₃; X=SCH₃; R²=H;

R³=CH₂CH₃; Q=CH₂W

V=O V= S R¹4 =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula III

R¹=H; X=OH; Q=CH₂W

R²=H; R3_βCH₃

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula III

R¹=CH₂CH₃; X=SCH₃; R²=H;

R³=CH₂CH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH3

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17;R¹⁷= =H W=W-18;V=O W=W-19

W-W-17; R¹⁷= =F W=W-18;V=S

W=W-17; R¹⁷=CH₃ W=W-18;V=NCH₃

Q=Q-1 Rδ=H Q=Q-7 ,R⁸=H

Q=Q-3 R^β=H Q=Q-8 R⁸=H

Q=Q-5 R⁸=H Q=Q-15;R⁸=H

Q=Q-6; R⁸=H

TABLE 4

Formula IV R¹=H; X=OH; R¹=H; X=SCH₃; R¹=CH₃; X=OCH₃; R¹=CH₃; X=O₂CCH₃;

Q=CH₂W; R²=H; Q=CH₂W; R²=CH₃; Q=CH₂W; R²=H; Q=CH₂W; R²=CH₃; R³=CH₂CH₃; R³=CH₂CH₃; R3=CH₂CH₃; R³=CH₃; W=W-1

W=W-1 W=W-1 W=W-1

R¹² R¹³ R¹² R¹³ R¹² R¹³ R¹² R¹³

F H F H F H F H

F F F F F F F F

Cl H Cl H Cl H Cl H

Cl F Cl F Cl F Cl F

Cl Cl Cl Cl Cl Cl Cl Cl

Br H Br H Br H Br H

CN H CN H CN H CN H

CH₃ H CH₃ H CH₃ H CH₃ H

CH₂CH₃ H CH₂CH₃ H CH₂CH₃ H CH₂CH₃ H

OCH₃ H OCH₃ H OCH₃ H OCH₃ H

SCH₃ H SCH₃ H SCH₃ H SCH₃ H

FCH₂ H FCH₂ H FCH₂ H FCH₂ H

F₂CH H F₂CH H F₂CH H F₂CH H

F₃C H F₃C H F₃C H F₃C H

F₂CHO H F₂CHO H F₂CHO H F₂CHO H

F₃CO H F₃CO H F₃CO H F₃CO H

CH=CH₂ H CH=CH₂ H CH=CH₂ H CH=CH₂ H

C≡CH H C≡CH H C≡CH H C≡CH H

Formula IV

R¹=CH₂CH₃; R¹=CH₂CH₃;

X=OH; R²= =CH₃; X=SCH₃; R²= H;

R³=CH₂CH₃; R³=CH₃; W=W-1

Q=CH₂W; W=W-1

R¹² R¹³ R¹² R¹³

F H F H

F F F F

Cl H Cl H

Cl F Cl F

Cl Cl Cl Cl

Br H Br H

CN H CN H

CH₃ H CH₃ H

CH₂CH₃ H CH₂CH₃ H

OCH₃ H OCH₃ H

SCH₃ H SCH₃ H

FCH₂ H FCH₂ H

F₂CH H F₂CH H

F₃C H F₃C H

F₂CHO H F₂CHO H

F₃CO H F₃CO H

CH=CH₂ H CH=CH₂ H

C≡CH H C≡CH H

Formula IV

R¹=H; X=OH; R²=H;

R³=CH₂CH₃; Q=CH₂W

V=O V=S R¹⁴=H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula IV

R¹=H; X=OH; Q=CH₂W

R²=H; R³=CH₂CH₃

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F H CH₃ H CH₃ H CH₃

F H F H F H F F F F F F F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H CH₃ F CH₃ F CH₃ F CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula IV

R¹= H; X=OH; R²=H;

R³=CH₂CH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1, R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6 R⁸=H

Formula IV

R¹=H; X=SCH₃; R²=CH₃;

R³=CH₂CH₃; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula IV

R¹=H; X=SCH₃; Q=CH₂W

R²=CH₃; R³=CH₂CH₃

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃ CH₃ H CH₃ H CH₃ H CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula IV

R¹=H; X=SCH₃; R²=CH₃;

R³=CH₂CH₃; Q=CH₂W

W= W-13 W=W-14 W= W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷ =F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1 ; R⁸=H Q=Q-7 ; R⁸=H

Q=Q- ; R⁸=H Q=Q-8;R⁸=H

Q=Q- ; R⁸=H Q=Q-15; R⁸=H

Q=Q-6 ; R⁸=H

Formula IV

R¹=CH₃; X=OCH₃; R²=H;

R³=CH₂CH₃; Q=CH₂W

V=O V= S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula IV

R¹=CH₃; X=OCH₃; Q=CH₂W

R²=H;R³=CH₂CH₃

W=W-11 W=W-12 W=W-15

V= O V=O V =O

R¹⁷ R¹⁸ R¹⁷ Rlδ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula IV

R¹=H; X=SCH₃; R²=CH₃;

R³=CH₂CH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula IV

R¹=CH₃; X=O₂CCH₃; R²=CH₃;

R³=CH₃; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula IV

R¹=CH₃; X=O₂CCH₃; Q=CH₂W

R²=CH₃; R³=CH₃

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula IV

R¹=CH₃; X=OCH₃; R²=H;

R³=CH₂CH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula IV

R¹=CH2CH₃; X=OH; R²=CH₃;

R³=CH₂CH₃; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W4 H

W-8 CH₃ W-8 CH₃ W4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula IV

R¹=CH₂CH₃; X=OH; Q=CH₂W

R²=CH₃; R³=CH₂CH₃

W=W-11 W=W-12 W=W-15

V= O V =O V =O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ 8¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V=S V=S V=S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H CH₃ F CH₃ F CH₃ F

CH3 CH₃ CH₃ CH₃ CH₃ CH₃

Formula IV

R¹=CH₂CH₃; X=OH; R²=CH₃;

R³=CH₂CH₃; Q=CH₂W

W=W-13 W=W-14 W= W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁶ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7 ; R⁸=H

Q=Q-3; R⁸=H Q=Q-8 ; R⁸=H

Q=Q-5; R₈=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula IV

R¹=CH₂CH₃; X=SCH₃; R²=H;

R³=CH₃; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula IV

R¹=CH₂CH₃; X=SCH₃; Q=CH₂W

R²=H; R³=CH₃

W=W-11 W=W-12 W=W-15

V=O V =O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V=S V=S V=S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula IV

R¹=CH₂CH₃; X=SCH₃; R²=H;

R³ =CH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16 R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H H F H F H F H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H CH₃ F CH₃ F CH₃ F CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

TABLE 5

Formula V

R¹=CH₃; R¹³=H; R¹=CH₃; R¹³ =F;

Q=CH₂W; W=W-1; Q=CH₂W; W=W-1;

X=OCH₃ X=OCH₃

R¹² R¹²

F CH₂CH₂CH₃ F CH₂CH₂CH₃

Cl CH(CH₃)₂ Cl CH(CH₃)₂

Br OCH₂CH₃ Br OCH₂CH₃

OH SCH₂CH₃ OH SCH₂CH₃

CN F₃CCH₂ CN F₃CCH₂

CH₃ C1CH₂CH₂O CH₃ C1CH₂CH₂O

CH₂CH₃ F₃CCH₂O CH₂CH₃ F₃CCH₂O

OCH₃ CH=CH₂ OCH₃ CH=CH₂

SCH₃ CH=CHCH₃ cis SCH₃ CH=CHCH₃ cis

FCH₂ CH=CHCH₃ trans FCH₂ CH=CHCH₃ trans

F₂CH. CH₂CH=CH₂ F₂CH CH₂CH=CH₂

F₃C CH₂CH₂CH=CH₂ F₃C CH₂CH₂CH=CH₂

ClCH₂ CH₂CH=CHCH₃ cis C1CH₂ CH₂CH=CHCH₃ cis

FCH₂O CH₂CH=CHCH₃ trans FCH₂O CH₂CH=CHCH₃ trans

F₂CHO C≡CCH₃ F₂CHO C≡CCH₃

F₃CO CH₂C≡CH F₃CO CH₂C≡CH

C≡CH CH₂C≡CCH₃ C≡CH CH₂C≡CCH₃

Formula V

R¹=CH_3; R¹³-Cl

Q=CH₂W; W=W-1;

X=OCH₃;

R¹²

F CH₂CH₂CH₃

Cl CH(CH₃)₂

Br OCH₂CH₃

OH SCH₂CH₃

CN F₃CCH₂

CH₃ CICH₂CH₂O

CH₂CH₃ F₃CCH₂O

OCH₃ CH=CH₂

SCH₃ CH=CHCH₃ cis

FCH₂ CH=CHCH₃ trans

F₂CH CH₂CH=CH₂

F₃C CH₂CH₂CH=CH₂

C1CH₂ CH₂CH=CHCH₃ cis

FCH₂O CH₂CH=CHCH₃ trans

F₂CHO C≡CCH₃

F₃CO CH₂C≡CH

C≡CH CH₂C≡CCH₃

Formula V

R¹=CH₃, Q=CH₂W,X=OCH₃

W=W-2 W=W-3 W=W-4 W=W-5

R¹⁴ R¹⁵ R¹⁴ R¹⁵ R¹⁴ R^lδ R¹⁴ R¹⁵

H H H H H H H H

F H F H F H F H

CH₃ H CH₃ H CH₃ H CH₃ H

OCH₃ H OCH₃ H OCH₃ H OCH₃ H

H CH₃ H CH₃ H CH₃ H CH₃

F CH₃ F CH₃ F CH₃ F CH₃

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

OCH₃ CH₃ OCH₃ CH₃ OCH₃ CH₃ OCH₃ CH₃ Formula V

R¹=CH₃, Q=CH₂W, X =OCH₃, W=W-6

R¹⁴ R¹⁶ R¹⁴ R¹⁶

H H H CH₃

F H F CH₃

CH₃ H CH₃ CH₃

OCH₃ H OCH₃ CH₃

H F H OCH₃

CH₃ F CH₃ OCH₃

OCH₃ F OCH₃ OCH₃

O Formula V

R¹=CH₃, X=OCH₃, Q=CH₂W

W=W-7 W=W-8 W=W-9 W=W-10

R¹⁷ V R¹⁷ V R¹⁷ V R¹⁷ V

H O H O H O H O

F O F O F O F O

Cl O Cl O Cl O Cl O

Br O Br O Br O Br O

CH₃ O CH₃ O CH₃ O CH₃ O

OCH₃ O OCH₃ O OCH₃ O OCH₃ O

H S H S H S H S

F S F S F S F S

Cl S Cl S Cl S Cl S

Br S Br S Br S Br S

CH₃ S CH₃ S CH₃ S CH₃ S

OCH₃ S OCH₃ S OCH₃ S OCH₃ S

H NH NH NH NH NH NH NH

F NH F NH F NH F NH

Cl NH Cl NH Cl NH Cl NH

Br NH Br NH Br NH Br NH

CH₃ NH CH₃ NH CH₃ NH CH₃ NH

OCH₃ NH OCH₃ NH OCH₃ NH OCH₃ NH

H NCH₃ H NCH₃ H NCH₃ H NCH₃

F NCH₃ F NCH₃ F NCH₃ F NCH₃

Cl NCH₃ Cl NCH₃ Cl NCH₃ Cl NCH₃

Br NCH₃ Br NCH₃ Br NCH₃ Br NCH₃

CH₃ NCH₃ CH₃ NCH₃ CH₃ NCH₃ CH₃ NCH₃

OCH₃ NCH₃ OCH₃ NCH₃ OCH₃ NCH₃ OCH₃ NCH₃

Formula V

R¹=CH₃, X-=OCH₃, Q=CH₂W

W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H Br

F H F Br

Cl H Cl Br

Br H Br Br

CH₃ H CH₃ Br

OCH₃ H OCH₃ Br

H F H CH₃

F F F CH₃

Cl F Cl CH₃

Br F Br CH₃

CH₃ F CH₃ CH₃

OCH₃ F OCH₃ CH₃

H Cl H OCH₃

F Cl F OCH₃

Cl Cl Cl OCH₃

Br Cl Br OCH₃

CH₃ Cl CH₃ OCH₃

OCH₃ Cl OCH₃ OCH₃

Formula V

R¹=CH₃, X=OCH₃

Q=CH₂W Q=Q-1, R⁸H

W=W-17 W=W-18 Q=Q-2, R⁸H

R¹⁷ V Q=Q-3, R⁸H

Q=Q-4, R⁸H,R¹¹=CH₃H O Q=Q-5, R⁸H

F S Q=Q-6, R⁸H

Cl NH Q=Q-7, R⁸H

Br NCH ₃ Q=Q-8, R⁸H

CH₃ Q=Q-9, R⁸H, R¹¹=CH₃ OCH₃ Q=Q-10, R⁸H, R¹¹=CH₃

Q=Q-11, R⁸H

W=W-19 Q=Q-12, R⁸H

Q=Q-13, R⁸H

Q=Q-14, R⁸H

Q=Q-15, R⁸H

Formula V Formula V

R¹=CH₂CH₃, X=OCH₃, R¹=CH₂CH₃ , X=OCH₃,

Q=CH₂W, W=W-1, R¹³=H Q=CH₂W, W =W-1, R¹³=F

R¹² R¹²

F CH₂CH₂CH₃ F CH₂CH₂CH₃

Cl CH(CH₃)₂ Cl CH(CH₃)₂

Br OCH₂CH₃ Br OCH₂CH₃

OH SCH₂CH₃ OH SCH₂CH₃

CN F₃CCH₂ CN F₃CCH₂

CH₃ C1CH₂CH₂O CH₃ ClCH₂CH₂O

CH₂CH₃ F₃CCH₂O CH₂CH₃ F₃CCH₂O

OCH₃ CH=CH₂ OCH₃ CH=CH₂

SCH₃ CH=CHCH₃ cis SCH₃ CH=CHCH₃ cis

FCH₂ CH=CHCH₃ trans FCH₂ CH=CHCH₃ trans

F₂CH CH₂CH=CH₂ F₂CH CH₂CH=CH₂

F₃C CH₂CH₂CH=CH₂ F₃C CH₂CH₂CH=CH₂

C1CH₂ CH₂CH=CHCH₃ cis C1CH₂ CH₂CH=CHCH₃ cis

FCH₂O CH₂CH=CHCH₃ trans FCH₂O CH₂CH=CHCH₃ trans

F₂CHO C≡CCH₃ F₂CHO C≡CCH₃

F₃CO CH₂ C≡CH F₃CO CH₂ C≡CH

C≡CH CH₂ C≡CCH₃ C≡CH CH₂ C≡CCH₃

Formula V

R¹=CH₂CH₃, X=OCH₃, Q=CH₂W

W=W-1, R¹³: =Cl

R¹²

F CH₂CH₂CH₃

Cl CH(CH₃)₂

Br OCH₂CH₃

OH SCH₂CH₃

CN F₃CCH₂

CH₃ ClCH₂CH₂O

CH₂CH₃ F₃CCH₂O

OCH₃ CH=CH₂

SCH₃ CH=CHCH₃ cis

FCH₂ CH=CHCH₃ trans

F₂CH CH₂CH=CH₂

F₃C CH₂CH₂CH=CH₂ ClCH₂ CH₂CH=CHCH₃ cis

FCH₂O CH₂CH=CHCH₃ trans

F₂CHO C≡CCH₃

F₃CO CH₂C≡CH

C≡CH CH₂C≡CCH₃

Formula V

R¹=CH₂CH₃, X=OCH₃, Q=CH₂W

W=W-2 W=W-3 W=W4 W=W-5

R¹⁴ R¹⁸ R¹⁴ R¹⁸ R¹⁴ R¹⁸ R¹⁴ R¹⁵

H H H H H H H H

F H F H F H F H

CH₃ H CH₃ H CH₃ H CH₃ H

OCH₃ H OCH₃ H OCH₃ H OCH₃ H

H CH₃ H CH₃ H CH₃ H CH₃

F CH₃ F CH₃ F CH₃ F CH₃

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

OCH₃ CH₃ OCH₃ CH₃ OCH₃ CH₃ OCH₃ CH₃

Formula V

R¹=CH₂CH₃, X=OCH₃, Q=C_H2W, W=W-6

R¹⁴ R¹⁶ R¹⁴ R¹⁶

H H H CH₃

F H F CH₃

CH₃ H CH₃ CH₃

OCH₃ H OCH₃ CH₃

H F H OCH₃

F F F OCH₃

CH₃ F CH₃ OCH₃

OCH₃ F OCH₃ OCH₃

Formula V

R¹=CH₂CH₃, X=OCH₃

Q=CH₂W Q=Q-1, R⁸=H

W=W-17 W=W-18 Q=Q-2, R⁸=H

R¹⁷ V Q=Q-3, R⁸=H

Q=Q-4, R⁸=H, R¹l=CH₃ H O Q=Q-5, R⁸=H

F S Q=Q-6, R⁸=H

Cl NH Q=Q-7, R⁸=H

Br NCH₃ Q=Q-8, R⁸=H

CH₃ Q=Q-9, R⁸=H, R¹¹=CH₃ OCH₃ Q=Q-10, R⁸=H, R¹l=CH₃

Q=Q-11, R⁸=H

W=W-19 Q=Q-12, R⁸=H

Q=Q-13, R⁸=H

Q=Q-14, R⁸=H

Q=Q-15, R⁸=H

Formula V Formula V

R¹=CH₃, X=OCD₃, Q=CH₂W R¹=CH₃, X=OCD₃, Q=CH₂W

W=W-1, R¹³=H W=W-1, R¹³=F R¹² R¹²

F CH₂ CH₂CH₃ F CH₂CH₂CH₃

Cl CH(CH₃₎2 Cl CH(CH₃)₂

Br OCH₂CH₃ Br OCH₂CH₃

OH SCH₂ CH₃ OH SCH₂CH₃

CN F₃CCH₂ CN F₃CCH₂

CH₃ ClCH₂CH₂O CH₃ ClCH₂CH₂O

CH₂CH₃ F₃CCH₂ O CH₂CH₃ F₃CCH₂O

OCH₃ CH=CH₂ OCH₃ CH=CH₂

SCH₃ CH=CHCH₃ cis SCH₃ CH=CHCH₃ cis

FCH₂ CH=CHCH₃ trans FCH₂ CH=CHCH₃ trans

F₂CH CH₂CH=CH₂ F₂CH CH₂CH=CH₂

F₃C CH₂CH₂CH=CH₂ F₃C CH₂CH₂CH=CH₂ ClCH₂ CH₂CH =CHCH₃ cis CICH₂ CH₂CH=CHCH₃ cis

FCH₂O CH₂CH=CHCH₃ trans FCH₂O CH₂CH=CHCH₃ trans

F₂CHO C≡CCH₃ F₂CHO C≡CCH₃

F₃CO CH₂OCH F₃CO CH₂C≡CH

C≡CH CH₂CH≡CCH₃ C≡CH CH₂CH≡CCH₃

Formula V

R¹=CH₃, X=OCD₃, Q=CH₂W

W =W-1, R¹³=Cl

R¹²

F CH₂CH₂CH₃

Cl CH(CH₃)₂

Br OCH₂CH₃

OH SCH₂CH₃

CN F₃CCH₂

CH₃ ClCH₂CH₂O

CH₂CH₃ F₃CCH₂O

OCH₃ CH=CH₂

SCH₃ CH=CHCH₃ cis

FCH₂ CH=CHCH₃ trans

F₂CH CH₂CH=CH₂

F₃C CH₂CH₂CH=CH₂

ClCH₂ CH₂CH=CHCH₃ cis

FCH₂O CH₂CH=CHCH₃ trans

F₂CHO C=CCH₃

F₃CO CH₂OCH

C=CH CH₂OCCH₃

Formula V

R¹=CH₃, X=OCD₃, Q=CH₂W

W=W-2 W=W-3 W=W-4 W=W-5

R¹⁴ R¹⁸ R¹⁴ R¹⁸ R¹⁴ R¹⁸ R¹⁴ R¹⁵

H H H H H H H H

F H F H F H F H

CH₃ H CH₃ H CH₃ H CH₃ H

OCH₃ H OCH₃ H OCH₃ H OCH₃ H

H CH₃ H CH₃ H CH₃ H CH₃

F CH₃ F CH₃ F CH₃ F CH₃

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

OCH₃ CH₃ OCH₃ CH₃ OCH₃ CH₃ OCH₃ CH₃

Formula V

R¹=CH₃, Q=CH₂W, X=OCD₃, W=W-6 R¹⁴ R¹⁶ R¹⁴ R¹⁶

H H H CH₃

F H F CH₃

CH₃ H CH₃ CH₃

OCH₃ H OCH₃ CH₃

H F H OCH₃

CH₃ F CH₃ OCH₃

OCH₃ F OCH₃ OCH₃

Formula V

R¹=CH₃, X=OCD₃, Q=CH₂W

W= W-7 W=W-8 W=W-9 W=W-10

R¹⁷ V R¹⁷ V R¹⁷ V R¹⁷ V

H O H O H O H O

F O F O F O F O

Cl O Cl O Cl O Cl O

Br O Br O Br O Br O

CH₃ O CH₃ O CH₃ O CH₃ O

OCH₃ O OCH₃ O OCH₃ O OCH₃ O

H S H S H S H S

F S F S F S F S

Cl S Cl S Cl S Cl S

Br S Br S Br S Br S

CH₃ S CH₃ S CH₃ S CH₃ S

OCH₃ S OCH₃ S OCH₃ S OCH₃ S

H NH NH NH H NH NH NH

F NH F NH F NH F NH

Cl NH Cl NH ci NH Cl NH

Br NH Br NH Br NH Br NH

CH₃ NH CH₃ NH CH₃ NH CH₃ NH

OCH₃ NH OCH₃ NH OCH₃ NH OCH₃ NH

H NCH₃ H NCH₃ H NCH₃ H NCH₃

F NCH₃ F NCH₃ F NCH₃ F NCH₃

Cl NCH₃ Cl NCH₃ Cl NCH₃ Cl NCH₃

Br NCH₃ Br NCH₃ Br NCH₃ Br NCH₃

CH₃ NCH₃ CH₃ NCH₃ CH₃ NCH₃ CH₃ NCH₃

OCH₃ NCH₃ OCH₃ NCH₃ OCH₃ NCH₃ OCH₃ NCH₃

Formula V

R¹ =CH₃, X=OCD₃, Q=CH₂W

W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H Br

F H F Br

Cl H Cl Br

Br H Br Br

CH₃ H CH₃ Br

OCH₃ H OCH₃ Br

H F H CH₃

F F F CH₃

Cl F Cl CH₃

Br F Br CH₃

CH₃ F CH₃ CH₃

OCH₃ F OCH₃ CH₃

H Cl H OCH₃

F Cl F OCH₃

Cl Cl Cl OCH₃

Br Cl Br OCH₃

CH₃ Cl CH₃ OCH₃

OCH₃ Cl OCH₃ OCH₃

Formula V

R¹=CH₃,X=OCD₃

Q=CH₂W Q=Q-1, R⁸=H

W=W-17 W=W-18 Q=Q-2, R⁸=H

R¹⁷ V Q=Q-3,R⁸=H

Q=Q-4, R⁸=H, R¹¹=CH₃ H O Q=Q-5,R⁸=H

F S Q=Q-6, R⁸=H

Cl NH Q=Q-7,R⁸=H

Br NCH₃ Q=Q-8,R⁸=H

CH₃ Q=Q-9, R⁸=H, RH=CH₃ OCH₃ Q=Q-10, R⁸=H, R¹¹=CH₃

Q=Q-11,R⁸=H

W=W-19 Q=Q-12, R⁸=H

Q=Q-13, R⁸=H

Q=Q-14, R⁸=H

Q=Q-15, R⁸=H

Formula V Formula V Formula V

R¹=H, X=OH, R¹=CH₃, R¹=CH₂CH₃, X=SCH₃;

Q=CH₂W, W=W-1 X=OCH₂CH₃; Q=CH₂W Q=CH₂W, W=W-1

W=W-1

R¹² R¹³ R¹² R¹³ R¹² R¹³

F H F H F H

F F F F F F

Cl H Cl H Cl H

Cl F Cl F Cl F

Cl Cl Cl ci Cl Cl

Br H Br H Br H

CN H CN H CN H

CH₃ H CH₃ H CH₃ H

CH₂CH₃ H CH₂CH₃ H CH₂CH₃ H

OCH₃ H OCH₃ H OCH₃ H

SCH₃ H SCH₃ H SCH₃ H

FCH₂ H FCH₂ H FCH₂ H

F₂CH H F₂CH H F₂CH H

F₃C H F₃C H F₃C H

F₂CHO H F₂CHO H F₂CHO H

F₃CO H F₃CO H F₃CO H

CH=CH₂ H CH=CH₂ H CH=CH₂ H

C≡CH H C≡CH H C≡CH H

Formula V

R¹=H; X=OH; Q=CH₂W

V=O V= S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula V

R¹=H; X=OH; Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V=O V=O R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H H F H F H F H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula V

R¹=H; X=OH; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q- 7; R⁸=H

Q=Q-3; R⁸=H Q=Q-6 ; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula V

R¹=CH₃; X=OCH₂CH₃; Q=CH₂W

V=O V= S R¹⁴=H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula V

R¹=CH₃;X=OCH₂CH₃; Q=CH₂W

W=W-11 W=W-12 W=W-15

V =O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V=S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula V

R¹=CH₃; X=OCH₂CH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W-W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q:3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula V

R¹=CH₂CH₃; X=SCH₃; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula V

R¹=CH₂CH₃;X=SCH₃; Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula V

R¹=CH₂CH₃; X=SCH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17;R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18;V=S

W=W-17;R¹⁷=CH₃ W=W-18;V=NCH₃

Q=Q-1; R⁸=H Q=Q-7 ;R⁸=H

Q=Q-3; R⁸=H Q=Q-8 ;R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q=6 ;R⁸=H

Formula V Formula V Formula V

R¹=H, X=O₂CCH₃, R¹=CH₃, X =O₂CPh, R¹=CH₂CH₃, X=Cl,

Q=CH₂W, W=W-1 Q=CH₂W, W=W-1 Q=CH₂W, W=W-1

R¹² R¹³ R¹² R¹³ R¹² R¹³

F H F H F H

F F F F F F

Cl H Cl H Cl H

Cl F Cl F Cl F

Cl Cl Cl Cl Cl Cl

Br H Br H Br H

CN H CN H CN H

CH₃ H CH₃ H CH₃ H

CH₂CH₃ H CH₂CH₃ H CH₂CH₃ H

OCH₃ H OCH₃ H OCH₃ H

SCH₃ H SCH₃ H SCH₃ H

FCH₂ H FCH₂ H FCH₂ H

F₂CH H F₂CH H F₂CH H

F₃C H F₃C H F₃C H

F₂CHO H F₂CHO H F₂CHO H

F₃CO H F₃CO H F₃CO H

CH=CH₂ H CH=CH₂ H CH=CH₂ H

OCH H C≡CH H C-CH H

R¹=H; X=O₂CCH₃; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula V

R¹=H; X=O₂CCH₃; Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula V

R¹=H; X=O₂CCH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1 R⁸=H Q=Q-7; R⁸=H

Q=Q-3 R⁸=H Q=Q-8; R⁸ =H

Q=Q-5 R⁸=H Q=Q-15; R⁸=H

Q=Q-6 R⁸=H

Formula V

R¹=CH₃; X=O₂CPh; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula V

R¹=CH₃; X=O₂CPh; Q=CH₂W

W=W-11 W= W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V =S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula V

R¹=CH₃; X=O₂CPh; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W-W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q-Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8 ; R⁸=H

Q=Q-6; R⁸=H Q=Q-15; R⁸=H

Formula V

R¹=CH₂CH₃; X=Cl; Q; =CH₂W

V=O V= S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula V

R¹=CH₂CH₃; X=Cl Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V =O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V =S V= S V=S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula V

R¹ =CH₂CH₃; X=Cl; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W-W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W-W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7 ; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6 ; R⁸=H

Formula V

R¹=H;X=N(CH₃)₂; Q=CH₂W

V=O V= S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula V

R¹=H; X=N(CH₃)₂; Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula V

R¹=H₂CH₃;X=:N(CH₃)₂; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18;V=O W=W-19

W=W-17; R¹⁷=F W=W-18;V=S

W=W-17; R¹⁷=CH₃ W=W-18;V=NCH₃

Q=Q-1 ;R⁸=H Q=Q-7; R⁸==

Q=Q-3 ;R⁸=H Q=Q-8;R⁸=H

Q=Q-5 ;R⁸=H Q=Q-15;R⁸=H

Q=Q-6 ;R⁸=H

Formula V

R¹=CH₂CH₃; X=OCH₂CH₂OH; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula V

R¹=CH₂CH₃; X=OCH₂CH₂OH; Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V=O V=O R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH3

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula V

R¹=CH₂CH₃; X=OCH₂CH₂OH; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W-W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula V Formula V Formula V R¹=H; R¹=CH₃; R¹=CH₂CH₃;

X=OCH₂CH₂OCH₃; X=OCH₂CH₂O₂CPh; X=OCHF₂;

Q=CH₂W; W=W-1 Q=CH₂W; W=W-1 Q=CH₂W; W=W-1 R¹² R¹³ R¹² R¹⁸ R¹² R¹³

F H F H F H

F F F F F F

Cl H Cl H Cl H

Cl F Cl F Cl F

Cl Cl Cl Cl Cl Cl

Br H Br H Br H

CN H CN H CN H

CH₃ H CH₃ H CH₃ H

CH₂CH₃ H CH₂CH₃ H CH₂CH₃ H

OCH₃ H OCH₃ H OCH₃ H

SCH₃ H SCH₃ H SCH₃ H

FCH₂ H FCH₂ H FCH₂ H

F₂CH H F₂CH H F₂CH H

F₃C H F₃C H F₃C H

F₂CHO H F₂CHO H F₂CHO H

F₃CO H F₃CO H F₃CO H

CH=CH₂ H CH=CH₂ H CH=CH₂ H

C≡CH H C≡CH H C≡CH H

Formula V

R¹=H; X=OCH₂CH₂OCH₃; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula V

R¹=H; X=OCH₂CH₂OCH₃; Q= CH₂W

W= W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V =S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula V

R¹=H; X=OCH₂CH₂OCH₃; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q-Q-1 ; R⁸=H Q=Q-7; R⁸=H

Q=Q-3 ; R⁸=H Q=Q-8; R⁸=H

Q=Q-6; R⁸=H Q=Q-15; R⁸=H

Formula V

R¹=CH₃;X=OCH₂CH₂O₂CPh; Q=CH₂W

V=O V= S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula V

R¹=CH₃; X=OCH₂CH₂O₂CPh Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula V

R¹=CH₃;X -OCH₂CH₂O₂CPh; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R^1?=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7 ; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=H

Formula V

R¹=CH₂CH₃;X=OCHF₂; Q=CH₂W

V=O V=S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula V

R¹=CH₂CH₃; X=OCHF₂; Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V=O V=O R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ Formula V

R¹=CH₂CH₃; X=OCHF₂; Q=CH₂W

W=W-13 W=W-14 W=W-16

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R¹⁷=H W=W-18; V=O W=W-19

W=W-17; Rⁱ⁷=F W=W-18; V=S

W=W-17; R¹⁷=CH₃ W=W-18; V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; Rδ=H

Formula V

R¹ =CH₃;X=OCH₂CH=CH₂; Q=CH₂W

V=O V= S R¹⁴ =H

W R¹⁷ W R¹⁷ W R¹⁵

W-7 H W-7 H W-2 H

W-7 F W-7 F W-2 CH₃

W-7 CH₃ W-7 CH₃ W-3 H

W-8 H W-8 H W-3 CH₃

W-8 F W-8 F W-4 H

W-8 CH₃ W-8 CH₃ W-4 CH₃

W-9 H W-9 H W-5 H

W-9 F W-9 F W-5 CH₃

W-9 CH₃ W-9 CH₃ W-6 H

W-10 H W-10 H W-6 CH₃

W-10 F W-10 F

W-10 CH₃ W-10 CH₃

Formula V

R¹=CH₃;X=OCH₂CH=CH₂; Q=CH₂W

W=W-11 W=W-12 W=W-15

V=O V=O V=O

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

V= S V= S V= S

R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

Formula V

R¹=CH₃;X= =OCH₂CH=CH₂; Q=CH₂W

W=W-13 W=W-14 W=W-16 R¹⁷ R¹⁸ R¹⁷ R¹⁸ R¹⁷ R¹⁸

H H H H H H

H F H F H F

H CH₃ H CH₃ H CH₃

F H F H F H

F F F F F F

F CH₃ F CH₃ F CH₃

CH₃ H CH₃ H CH₃ H

CH₃ F CH₃ F CH₃ F

CH₃ CH₃ CH₃ CH₃ CH₃ CH₃

W=W-17; R^1?=H W=W-18; V=O W=W-19

W=W-17; R¹⁷=F W=W-18; V=S

W=W-17;R¹⁷=CH₃ W=W-18;V=NCH₃

Q=Q-1; R⁸=H Q=Q-7; R⁸=H

Q=Q-3; R⁸=H Q=Q-8; R⁸=H

Q=Q-5; R⁸=H Q=Q-15; R⁸=H

Q=Q-6; R⁸=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 6

Weight Percent*

Active

Ingredient Diluent(s) Surfactant(s)

Wettable Powders 5-60 39-94 1-10

Emulsifiable 3-80 20-95 0-20

Concentrates

Dusts 1-25 70-99 0-5 Granules and Pellets 0.1-50 50-99.9 0-15

*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, New Jersey, but other solids, either mined or manufac- tured, may be used. The more absorptive diluents arepreferred for wettable powders and the denser onesfor 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°C. "McCutcheon's Detergents and

Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, 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, micro- biological 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. Patent 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", Che mical Engineering. December 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. Patent 3,235,361, February 15, 1966, Col. 6, line

16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Patent 3,309,192, Marchl4, 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. Patent 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 and Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Hand- book", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

Example A

Wettable Powder

2-[(2-fluorophenyl)methoxy]-5-methoxy-1- methyl-9-oxabicyclo[3.3.1]-nonane 60%

sodium alkylnaphthalenesulfonate 2%

sodium Hgninsulfonate 2%

synthetic amorphous silica 36%

The active ingredient is first sprayed onto the amorphous silica, then the ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.

Example B Wettable Powder

2-[(2-fluorophenyl)methoxy]-5-methoxy-1- methyl-9-oxabicyclo[3.3.1]-nonane 50%

sodium alkylnaphthalenesulfonate 2%

low viscosity methyl cellulose 2%

diatomaceous earth 46% The active ingredient is first sprayed onto the diatomaceous earth then the ingredients are blended, coarsely hammer-milled and then airmilled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

Example C

Granule

Wettable Powder of Example B 5%

attapulgite granules 95%

(U.S.S. 20-40 mesh; 0.84-0.42 mm)

A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules aredried and packaged.

Example D

Emulsifiable Concentrate

2-[(2-fluorophenyl)methoxy]-5-methoxy-1- methyl-9-oxabicyclo[3.3.1]-nonane 40%

Atlox 3403F 3%

Atlox 3404F 3%

xylene 54%

The active ingredient and Atlox emulsifiers are dissolved in the solvent, filtered and packaged. Atlox 3403F and 3404F are blends of anionic and ionic emulsifiers from ICI Americas, Inc.

Example E

Low Strength Granule

2-[(2-fluorophenyl)methoxy]-5-methoxy-1- methyl-9-oxabicyclo[3.3.1]-nonane 5%

attapulgite granules 95%

(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 F

Granule

2-[(2-fluorophenyl)methoxy]-5-methoxy-1- methyl-9-oxabicyclo[3.3.1]-nonane 50%

wetting agent 1%

crude ligninsulfonate salt (containing 10%

5-20% of the natural sugars)

attapulgite clay 39%

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 fhiidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidiza- tion 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 packagedfor use.

Example G

Concentrated Emulsion

2-[(2-fluorophenyl)methoxy]-5-methoxy-1- methyl-9-oxabicyclo[3.3.1]-nonane 25%

xylene 25%

Atlox 3404F 5%

G1284 5%

ethylene glycol 8%

water 32%

The active ingredient, solvent and emulsifiers are blended together. This solution is added to a mixture of the ethylene glycol and water with stirring. Example H

Solution

2-[(2-fluorophenyl)methoxy]-5-methoxy-1- methyl-9-oxabicyclo[3.3.1]-nonane 5%

water 95%

The compound is added directly to the water with stirring to produce the solution, which may then be packaged for use.

Exa mp le I

Dust

2-[(2-fluorophenyl)methoxy]-5-methoxy-1- methyl-9-oxabicyclo[3.3.1]-nonane 10%

attapulgite 10%

Pyrophyllite 80%

The active ingredient is sprayed onto the attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.

Utility

Test results indicate compounds of this invention are active postemergence and, in particular, preemergence herbicides. Many compounds in this invention are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops such as barley (Hordeu m vulgare), corn (Zsa mays), cotton (Gossypium hirsutum), rape (Brassica napus). rice (Oryza sativa). sorghum (So rghum bicolor). soybean (Glycine max), sugar beet (Beta vulgaris). wheat (Triticum aestivum), and vegetable crops. Grass and broadleaf weed species controlled include, but are not limited to, barnyardgrass (Eshinochloa crusgalli). crabgrass (Digitaria spp.), duck salad (Heteranthera limosa), foxtail (Setaria spp.), lambsquarters (Chenopodiu m spp.), and umbrella sedge (Cyperus difformis). Several compounds in this invention are particularly useful for the control of bamyardgrass and selected broadleaf weeds such as duck salad and umbrella sedge in upland and paddy rice.

These compounds also have utility for weed control of selected vegetation in specified areas such as around storage tanks, parking lots, highways, and railways; in fallow crop areas; and in citrus and plantation crops such as banana, coffee, oil palm, and rubber. Alternatively, these compounds are useful to modify plant growth.

Common Name Chemical Name acetochlor 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide acifluorfen 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid

acrolein 2-propenal alachlor 2-chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide anilofos S-4-chloro-N-isopropyIcarbaniloylmethyl-O,O- dimethyl phosphorodithioate ametryn N-ethyl-N-(1-methylethyl)-6-(methylthio)-1,3,5- triazine-2,4-diamine amitrole 1H-1,2,4-triazol-3-amine AMS ammonium sulfamate

asulam methyl [(4-aminophenyl)sulfonyl]carbamate atrazine 6-chloro-N-ethyl-N'-(1-methylethyl)-1,3,5- triazine-2,4-diamine barban 4-chloro-2-butynyl 3-chlorocarbamate benefin N-butyl-N-ethyl-2,6-dinitro-4-(trifluoromethyl)- benzenamine bensulfuron 2-[[[[[(4,6-dimethoxy-2-pyrimidmyl)amino]- methyl methylcarbonyl]amino]sulfonyl]methyl]benzoic acid, methyl ester bensulide O,O-bis( 1-methylethyl) S-[2-[(phenylsulfonyl)- amino]ethyl]phosphorodithioate Common Name Chemical Name bentazon 3-(l-methylethyl)-(1H)-2,l,3-benzothiadiazin- 4(3H)-one, 2,2-dioxide benzofluor N-[4-(ethylthio)-2-(trifluoromethyl)phenyl]- methanesulfonamide benzoylprop N-benzoyl-N-(3,4-dichlorophenyl)-DL-alanine bifenox methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate bromacil 5-bromo-6-methyl-3-(1-methylpropyl)- 2,4(1H,3H)pyrimidinedione bromoxynil 3,5-dibromo-4-hydroxybenzonitrile butachlor N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)- acetamide buthidazole 3-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-4- hydroxy-1-methyl-2-imidazoHdinone butralin 4-(1,1-dimethylethyl)-N-(1-methylpropyl)-2,6- dinitrobenzenamine butylate S-ethyl bis(2-methylpropyl)carbamothioate cacodylic acid dimethyl arsinic oxide CDAA 2-chloro-N,N-di-2-propenylacetamide CDEC 2-chloroallyl diethyldithiocarbamate CGA 142,464 3-(4,6-dimethoxy-1,3,5-triazin-2-yl)-1-[2-(2- methoxyethoxy)phenylsulfonyl]-urea chloramben 3-amino-2,5-dichlorobenzoic acid Common Name Chemical Name chlorbromuron 3-(4-bromo-3-chlorophenyl)-1-methoxy-1- methylurea chlorimuron ethyl 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)- ethylammo]carbonyl]amino]sιdfonyl]benzoic- acid, ethyl ester chlormethoxynil 2,4-dichlorophenyl-4-nitro-3-methoxyphenyl ether

chlornitrofen 2,4,6-trichlorophenyl-4-nitrophenyl ether chloroxuron N'-[4-(4-chlorophenoxy)phenyl]-N,N-dimethyl- urea chlorpropham 1-methylethyl-3-chlorophenylcarbamate chlorsulfuron 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-riazin-2- yl)amino]carbonyl]benzenesulfonamide chlortoluron N'-(3-chloro-4-methylphenyl)-N,N-dimethylurea cinmethylin exo-1-methyl-4-(1-methylethyl)-2-[(2-methylphenyl)methoxy]-7-oxabicyclo-[2.2.1]heptane clethodim (E,E)-(±)-2-[1-[[(3-chloro-2-propenyl)oxy]imino]- propyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2- cyclohexen-1-one clomazone 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3- isoxazolidinone cloproxydim (E,E)-2-[1-[[(3-chloro-2-propenyl)oxy)imino]- butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2- cyclohexen-1-one Common Name Chemical Name clopyralid 3,6-dichloro-2-pyridinecarboxylic acid

CMA calcium salt of MAA cyanazine 2-[[4-chloro-6-(ethylamino)-1,3,5-triazin-2- yl]amino]-2-methylpropanenitrile cycloate S-ethyl cyclohexylethylcarbamothioate cycluron 3-cyclooctyl-1,1-dimethylιιrea cyperquat 1-methyl-4-phenylpyridinium cyprazine 2-chloro-4-(cyclopropylamino)-6-(isopropylamino)-s-triazine cyprazole N-[5-(2-chloro-1,1-dimethylethyl)-1,3,4- thiadiazol-2-yl]cyclopropanecarboxamide cypromid 3',4'-dichlorocyclopropanecarboxanilide dalapon 2,2-dichloropropanoic acid dazomet tetrahydro-3,5-dimethyl-2H-1,3,5-thiadiazine-2- thione

DCPA dimethyl 2 ,3,5,6-tetrachloro-1,4-benzene

diearboxylate desmediphan ethyl [3-[[(phenylamino)carbonyl]oxy]- phenyl]carbamate

Common Name Chemical Name

desmetryn 2-(isopropylammo)-4-(methylamino)-6-(methyl- thio)-s-triazine diallate S-(2,3-dichloro-2-propenyl)bis(1-methylethyl)- carbamothioate dicamba 3,6-dichloro-2-methoxybenzoic acid dichlobenil 2 ,6-dichlorobenzonitrile dichlorprop (±)-2-(2,4-dichlorophenoxy)propanoic acid dichlofop (±)-2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid, methyl ester diethatyl N-(chloroacetyl)-N-(2,6-diethylphenyl)glycine difenzoquat 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium dimepiperate S-1-methyl-l-phenylethylpiperidine-1-carbothioate dinitramine N³,N³-diethyl-2,4-dinitro-6-(trifluoromethyl)-1,3- benzenediamine dinoseb 2-(1-methylpropyl)-4,6-dinitrophenol diphenamid N,N-dimethyl-α-phenylbenzeneacetamide dipropetryn 6-(ethylthio)-N,N'-bis(l-methylethyl)-1,3,5- triazine-2,4-diamine diquat 6,7-dihydrodipyrido[1,2-a:2',1'-c]-pyrazinedium ion diuron N'-(3,4-dichlorophenyl)-N,N-dimethylurea Common Name Chemical Name DNOC 2-methyl-4,6-dinitrophenol

DSMA disodium salt of MAA dymron N-(4-methylphenyl)-N-(1-methyl-1-phenylethyl)- urea endothall 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid

EPTC S-ethyl dipropylcarbamothioate esprocarb S-benzyl-N-ethyl-N-(1,2-dimethyl)propyl)- (SC2957) thiolcarbamate ethalfluralin N-ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4- (trifluoromethyl)benzenamine ethofumesate (±)-2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate fenac 2,3,6-trichlorobenzeneacetic acid fenoxaprop (±)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]- propanoic acid fenuron N,N-dimethyl-N'-phenylurea

fenuron TCA Salt of fenuron and TCA flamprop N-benzoyl-N-(3-chloro-4-fluorophenyl)-DL- alanine fluazifop (±)-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]- phenoxylpropanoic acid fluazifop-P (R)-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]- phenoxylpropanoic acid Common Name Chemical Name fluchloralin N-(2-chloroethyl)-2,6-dinitro-N-propyl-4- (trifluoromethyl)benzenamine fluometuron N,N-dimethyl-N'-[3-(trifluoromethyl)phenyl]urea fluorochloridone 3-chloro-4-(chloromethyl)-1-[3-(trifluoromethyl)- phenyl]-2-pyrrolidinone fluorodifen p-nitrophenyl a,a,a-trifluoro-2-nitro-p-tolyl ether fluoroglycofen carboxymethyl 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitrobenzoate fluridone 1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]- 4(1H)-pyridinone fomesafen 5-[2-chloro-4-(trifluoromethyl)phenoxy]N- (methylsulfonyl)-2-nitrobenz amide fosamine ethyl hydrogen (aminocarbonyl)phosphate glyphosate N-(phosphonomethyl)glycine haloxyfop 2-[4-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]- oxy]phenoxy]propanoic acid hexaflurate potassium hexafluoroarsenate hexazinone 3-cyclohexyl-6-(dimethylamino)-1-methyl-1,3,5- triazine-2,4(1H,3H)-dione imazamethabenz 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)- m-toluic acid, methyl ester and 6-(4-isopropyl- 4-methyl-5-oxo-2-imidazolin-2-yl)-p-toluic acid, methyl ester Common Name Chemical Name imazapyr (±)-2-[4,5-dihydro-4-methyl-4-(l-methyl-ethyl)-5- oxo-1H-imidazol-2-yl3-3-pyridinecarboxylic acid imazaquin 2-[4,5-dihydro-4-methyl-4-(l-methylethyl)-5-oxo- 1H-imidazol-2-yl3-3-quinolinecarboxylic acid imazethapyr (±)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5- oxo-1H-imidazol-2-yl]-5-ethyl-3-pyridinecarboxylic acid ioxynil 4-hydroxy-3,5-diiodobenzonitrile isopropalin 4-(l-methylethyl)-2,6-dinitro-N,N-dipropylbenzenamine isoproturon N-(4-isopropylphenyl)-N,N'-dimethylurea isouron N'-[5-(1,1-dimethylethyl)-3-isoxazolyl]-N,N- dimethylurea isoxaben N-[3-(1-ethyl-1-methylpropyl)-5-isoxazolyl]-2,6- dimethoxybenzamide karbutilate 3-[[(dimethylaιrrino)carbonyl]amino]phenyl-(1,1- dimethylethyl)carbamate

lactofen (±)-2-ethoxy-1-methyl-2-oxoethyl 5-[2-chloro-4- (trifluoromethyl)phenoxy]-2-nitrobenzoate lenacil 3-cyclohexyl-6,7-dihydro-1H-cyclopentapyrimidine-2,4(3H,5H)-dione linuron N'-(3,4-dichlorophenyl)-N-methoxy-N-methylurea

MAA methylarsonic acid

MAMA monoammonium salt of MAA Common Name Chemical Name

MCPA (4-chloro-2-methylphenoxy)acetic acid

MCPB 4-(4-chloro-2-methylphenoxy)butanoic

acid

MON 7200 S,S-dimethyl-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarbothionate

mecoprop (±)-2-(4-chloro-2-methylphenoxy) propanoic acid mefenacet 2-(2-benzothiazolyloxy-N-methyl-N-phenylacetamide mefluidide N-[2,4-dimethyl-5-[[(trifluoromethyl)sulfonyl]- amino]phenyl]acetamide

methalpropaHn N-(2-methyl-2-propenyl)-2,6-dinitro-N-propyl-4- (trifluoromethyl)benzenamide methabenzthiazuron 1,3-dimethyl-3-(2-benzothiazolyl)urea metham methylcarbamodithioic acid

methazole 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxa- diazolidine-3,5-dione methoxuron N'-(3-chloro-4-methoxyphenyl)-N,N-dimethylurea metolachlor 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2- methoxy-1-methylethyl)acetamide metribuzin 4-amino-6-(1,1-dimethylethyl)-3-(methylthio)- 1,2,4-triazin-5(4H)-one

Common Name Chemical Name metsulfuron methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)- amino]carbonyl]amino]sulfonyl]benzoic acid, methyl ester

MH 1,2-dihydro-3,6-pyridazinedione molinate S-ethyl hexahydro-1H-azepine-1-carbothioate monolinuron 3-(p-chlorophenyl)-1-methoxy-1-methylurea monuron N'-(4-chlorophenyl)-N,N-dimethylurea monuron TCA Salt of monuron and TCA

MSMA monosodium salt of MAA napropamide N,N-diethyl-2-(1-naphthalenyloxy)propanamide naptalam 2-[(1-naphthalenylamino)carbonyl]benzoic acid neburon 1-butyl-3-(3,4-dichlorophenyl)-1-methylurea nitralin 4-(methylsulfonyl)-2,6-dinitro-N,N-dipropylaniline nitrofen 2,4-dichloro-1-(4-nitrophenoxy)benzene nitrofluorfen 2-chloro-1-(4-nitrophenoxy)-4-(trifluoromethyl)- benzene norea N,N-dimethyl-N'-(octahydro-4,7-methano-1H- inden-5-yl)urea 3aa,4a,5a,7a,7aa-isomer norflurazon 4-chloro-5-(methylamino)-2-[3-(trifluoromethyl)- phenyl]-3(2H)-pyridazinone oryzalin 4-(dipropylamino)-3,5-dinitrobenzenesulfonamide Common Name Chemical Name oxadiazon 3-[2,4-dichloro-5-(1-methylethoxy)phenyl]-5-(1,1- dimethylethyl)-1,3,4-oxadiazol-2(3H)-one oxyfluorfen 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene paraquat 1,1'-dimethyl-4,4'-dipyridinium ion pebulate S-propyl butylethylcarbamothioate pendimethalin N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzenamine perfluidone 1,1,1-trifluoro-N-[2-methyl-4-(phenylsulfonyl)- phenyllmethanesulfonamide phenmedipham 3-[(methoxycarbonyl)amino]phenyl (3-methylphenyl)carbamate picloram 4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid

PPG-1013 5-[2-chloro-4-(trifluoromethyl)phenoxy3-2-nitroacetophenone oxime-O-acetic acid, methyl ester pretilachlor α-chloro-2,6-diethyl-N-(2-propoxyethyl)- acetanilide procyazine 2-[[4-chloro-6-(cyclopropylamino)-l,3,5-triazine- 2-yl]amino]-2-methylpropanenitrile profluralin N-(cyclopropylmethyl)-2,6-dinitro-N-propyl-4- (trifluoromethyl)benzenamine prometon 6-methoxy-N,N'-bis(l-methylethyl)-1,3,5- triazine-2,4-diamine Common Name Chemical Name

prometryn N,N'-bis(1-methylethyl)-6-(methylthio)-1,3,5- triazine-2,4-diamine pronamide 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)- benzamide propachlor 2-chloro-N-(1-methylethyl)-N-phenylacetamide propanil N-(3,4-dichlorophenyl)propanamide propazine 6-chloro-N,N'-bis(1-methylethyl)-1,3,5-triazine- 2,4-diamine propham 1-methylethyl phenylcarbamate prosulfalin N-[[4-(dipropylamino)-3,5-dinitrophenyl]- sulfonyl]-S,S-dimethylsulfilimine prynachlor 2-chloro-N-(1-methyl-2-propynyl)acetanilide pyrazolate 4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl- p-toluenesulphonate pyrazon 5-ammo-4-chloro-2-phenyl-3(2H)-pyridazinone pyrazosulfuron ethyl ethyl S-[3-(4,6-dimethoxypyrimidin-2-yl)ureadosulfonyl]-1-methylpyrazole-4-carboxylate quinclorac 3,7-dichloro-8-quinoline carboxylic acid quizalofop ethyl (±)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]- propanoic acid, ethyl ester secbumeton N-ethyl-6-methoxy-N'-(1-methylpropyl)-1,3,5- triazine-2,4-diamine Common Name Chemical Name sethoxydim 2-[1-(ethoxyimino)butyl]-5-[2-(ethylthio)propyl]- 3-hydroxy-2-cyclohexen-1-one siduron N-(2-methylcyclohexyl)-N'-phenylurea simazine 6-chloro-N,N'-diethyl-1,3,5-triazine-2,4-diamine

SK-233 1-(α,α-dimethylbenzyl)-3-(4-methylphenyl)urea sulfometuron methyl 2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]- carbonyl]amino]sulfonyl]benzoic acid, methyl ester

TCA trichloroacetic acid tebuthiuron N-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]- N,N-dimethylurea terbacil 5-chloro-3-(1,1-dimethylethyl)-6-methyl-2,4- ( 1H,3H)-pyrimidinedione terbuchlor N-(butoxymethyl)-2-chloro-N-[2-(1,1-dimethylethyl)-6-methylphenyl]acetamide terbuthylazine 2-(tert-butylamino)-4-chloro-6-(ethyl-amino)-striazine terbutol 2 ,6-di-tert-butyl-p-tolyl methylcarbamate terbutryn N-(1,1-dimethylethyl)-N'-ethyl-6-(methylthio)- 1,3,5-triazine-2,4-diamine thifensulfuron methyl 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)- amino3carbonyI]amino]sulfonyl]-2-thiophenecarboxylic acid, methyl ester Common Name Chemical Name thiobencarb S-[(4-chlorophenyl)methyl] diethylcarbamothioate triallate S-(2,3,3-trichloro-2-propenyl) bis(1-methylethyl)- carbamothioate tribenuron methyl 2-[[[[N-(4-methoxy-6-methyl-1,3,5-riazine-2-yl)- N-methylamino]carbonyl]amino]sulfonyl]- benzoic acid, methyl ester triclopyr [(3,5,6-trichloro-2-pyridinyl)oxy]acetic acid tridiphane 2-(3,5-dichlorophenyl)-2-(2,2,2-trichloroethyl)oxirane trifluralin 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)- benzenamine trimeturon 1-(p-chlorophenyl)-2,3,3-trimethylpseudourea

2,4-D (2,4-dichlorophenoxy)acetic acid

2,4-DB 4-(2,4-dichlorophenoxy)butanoic acid vernolate S-propyl dipropylcarbamothioate xylachlor 2-chloro-N-(2,3-dimethylphenyl)-N-(1-methylethyl)acetamide

Selective herbicidal properties of the subject compounds

were discovered in greenhouse tests as described below.

CMPD NO. NMR SPECTRAL DATA

1 (CDCl₃, 90 MHz,0 ¹H) δ 0.78 (m, 3H); 1.0-2.2 (m, 12H);

3.15 (brs, 1H); 4.38 (d, 1H, J=12Hz); 4.62 (d, 1H, J=12Hz); 7.35 (s, 5H).

2 (CDCI₃, 90 MHz, ¹H) δ 0.75 (t, 3H, J=7.5); 1.0-2.2 (m,

12H); 3.10 (brs, 1H); 3,64 (brs, 1H); 4.31 (d, 1H, J=12Hz);

4.58 (d, 1H, J=12Hz); 7.35 (s, 5H).

(CDCI₃, 100 MHz, ¹³C) δ 7.1, 19.5, 23.5, 28.6, 31.7, 32.2,

34.4, 70.7, 73.6, 80.1, 95.0, 127.3, 127.8, (x2), 128.0 (x2), 138.5.

3 (CDCI₃, 90 MHz, ¹H) δ 0.80 (t, 3H, J=7.5); 1.0-2.2 (m,

12H); 3.08 (brs, 1H); 3.34 (s, 3H); 4.38 (d, 1H, J=12Hz); 4.67 (d, 1H, J=12Hz); 7.36 (s, 5H).

4 (CDCI₃, 90 MHz, ¹H) δ 0.77 (t, 3H, J=7.5Hz); 1.16 (t, 3H,

J=7.5Hz); 1.0-2.2 (m, 12H); 3.03 (t, 1H, J=2Hz); 3.64 (q, 2H, J=7.5Hz); 4.38 (d, 1H, J=12Hz); 4.63 (d, 1H, J=12Hz); 7.33 (s, 5H).

5 (CDCI₃, 200 MHz, ¹H) δ 1.27 (d, 3H, J=3.4Hz); 1.2-2.2 (m,

8H); 2.66(d, 2H, J=10.6Hz); 3.07 (t, 1H, J=2.8Hz); 3.78 (s, 1H); 4.51 (d, 1H, J=12.1Hz); 4.69 (d, 1H, J=12.1Hz); 7.0- 7.6 (m, 4H). 6 (CDCI₃, 200 MHz, ¹H) δ 1.21 (s, 3H); 1.3-2.2 (m, 10H); 2.66 (s, 1H); 3.03 (t, 1H, J=2.8Hz); 4.51 (d, 1H, J=10.9Hz); 4.71 (d, 1H, J=10.9Hz); 6.88 (t, 2H, J=7.4Hz); 7.27

(quintet, 1H, J=7.4Hz).

7 (CDCI₃, 90 MHz, ¹H) δ 1.34 (s, 3H); 1.2-2.1 (m, 10H); 3.10

(t, 1H, J=3Hz); 3.38 (s, 3H); 4.53 (d, 1H, J=12Hz); 4.73 (d, 1H, J=12Hz); 6.8-7.6 (m, 4H).

8 (CDCI₃, 90 MHz, ¹H) δ 1.20 (s, 3H); 1.2-2.2 (m, 10H); 3.02

(t, 1H, J=3Hz); 3.32 (s, 3H); 4.50 (d, 1H, J=12Hz); 4.72 (d, 1H, J=12Hz); 6.90 (t, 2H, J=7.5Hz); 7.32 (quintet, 1H, J=7.5Hz).

9 (CDCI₃, 90 MHz, ¹H) δ 1.31 (ε, 3H); 1.2-2.2 (m, 10H); 3.02

(t, 1H, J=3H); 3.65 (brs, 1H); 4.40 (d, 1H, J=12Hz); 4.63 (d, 1H, J=12Hz); 7.34 (s, 5H).

10 (CDCI₃, 90 MHz, ¹H) δ 1.28 (s, 3H); 1.2-2.2 (m, 10H), 3.00

(t, 1H, J=3Hz); 3.34 (s, 3H); 4.40 (d, 1H, J=12Hz); 4.64 (d, 1H, J=12Hz); 7.34 (s, 5H).

11 (CDCl₃, 90 MHz, ¹H δ 1.16 (t, 3H, J=7.5Hz); 1.27 (s, 3H);

1.2-2.2 (m, 10H); 3.00 (t, 1H, J=3Hz); 3.67 (q, 2H,

J=7.5Hz); 4.40 (d, 1H, J=12Hz); 4.65 (d, 1H, J=12Hz); 7.35 (s, 5H).

12 (CDCI₃, 90 MHz, ¹H) δ 1.17 (t, 3H, J=7.5Hz); 1.27 (s, 3H);

1.2-2.2 (m, 10H); 3.05 (t, 1H, J=3Hz); 3.66 (q, 2H,

J=7.5Hz); 4.5 (d, 1H, J=12Hz); 4.70 (d, 1H, J=12Hz); 6.8- 7.6 (m,4H).

13 (CDCI₃, 90 MHz, ¹H) δ 1.17 (t, 3H, J=7.5Hz); 1.19 (s, 3H);

1.0-2.2 (m, 10H); 3.00 (t, 1H, J=3Hz); 3.64 (q, 2H,

J=7.5Hz); 4.51 (d, 1H, J=12Hz); 4.68 (d, 1H, J=12Hz); 6.90 (t, 2H, J=7.5Hz); 7.32 (quintet, 1H, J=7.5Hz). 14 (CDCl₃, 90 MHz, ¹H) δ 1.28 (s, 3H); 1.2-2.1 (m, 10H); 2.98 (t, 1H, J=3Hz); 4.40 (d, 1H, J=12Hz); 4.64 (d, 1H,

J=12Hz); 7.33 (s, 5H).

15 (CDCI₃, 90 MHz, ¹H) δ 1.30 (s, 3H); 1.2-2.2 (m, 10H); 3.04

(brs, 1H); 4.38 (d, 1H, J=12Hz); 4.62 (d, 1H, J=12Hz); 7.36 (s, 5H).

16 (CDCI₃, 90 MHz, ¹H) δ 1.27 (s, 3H); 1.2-2.2 (m, 10H); 3.00

(t, 1H, J=3Hz); 3.18 (brs, 1H); 3.68 (m, 4H); 4.38 (d, 1H, J=12Hz); 4.64 (d, 1H, J=12Hz); 7.34 (s, 5H).

17 (CDCI₃, 90 MHz, ¹H) δ 1.22 (s, 3H); 1.3-2.3 (m, 9H); 2.13

(s, 2H); 2.74 (s, 1H); 3.35 (d, 1H, J=7.5Hz); 3.88 (s, 4H); 4.43 (d, 1H, J=12Hz); 4.65 (d, 1H, J=12Hz); 7.37 (s, 5H).

18 (CDCI₃, 90 MHz, ¹H) δ 0.87 (t, 3H, J=7.5Hz); 1.2-2.1 (m,

9H); 3.43 (dd, 1H, J=6.6, 9.6Hz); 3.90 (s, 4H); 4.42 (d, 1H, J=12Hz); 4.62 (d, 1H, J=12Hz); 7.32 (s, 5H).

19 (CDCI₃, 90 MHz, ¹H) δ 1.24 (s, 3H); 1.3-2.3 (m, 12H); 3.46

(dd, 1H, J=2.0,7.5Hz); 3.92 (s, 4H); 4.55 (d, 1H, J=12Hz); 4.75 (d, 1H, J=12Hz); 7.2-7.5 (m, 4H).

20 (CDCI₃, 90 MHz, ¹H) δ 1.33 (s, 3H); 1.3-2.2 (m, 10H); 3.09

(t, 1H, J=3Hz); 3.16 (brs, 1H); 4.49 (d, 1H, J=12.5Hz); 4.72 (d, 1H, J=12.5Hz); 7.15-7.45 (m, 3H); 7.55-7.70 (m, 1H).

21 (CDCI₃, 90 MHz, ¹H) δ 0.90 (t, 3H, J=7.5Hz); 1.28 (s, 3H);

1.0-2.1 (m, 12H); 3.02 (t, 1H, J=3Hz); 3.55 (t, 2H,

J=7.5Hz); 4.45 (d, 1H, J=12Hz); 4.67 (d,lH, J=12Hz); 7.36 (s, 5H).

22 (CDCI₃, 90 MHz, !H) δ 1.28 (s, 3H); 1.0-2.2 (m, 10H); 3.00

(t, 1H, J=3Hz); 4.0 (m, 2H); 4.42 (d, 1H, J=12Hz); 4.65 (d, 1H, J=12Hz); 5.0-5.3 (m, 2H); 5.7-6.2 (m, 1H); 7.35 (s, 5H).

23 (CDCI₃, 90 MHz, ¹H) δ 1.21 (s, 3H); 1.2-2.1 (m, 11H); 3.02

(t, 1H, J=3Hz); 4.50 (d, 1H, J=12Hz); 4.72 (d, 1H, J=12Hz); 6.89 (t, 2H, J=7.5Hz); 7.30 (quintet, 1H,

J=7.5Hz).

24 (CDCl₃, 90 MHz, ¹H) δ 1.29 (s, 3H); 1.1-2.1 (m, 10H); 3.00

(t, 1H, J=3Hz); 4.40 (d, 1H, J=12Hz); 4.65 (d, 1H,

J=12Hz); 7.35 (s, 5H).

26 (CDCI₃, 90 MHz, ¹H) δ 1.27 (s, 3H); 1.1-2.2 (m, 10H); 3.00

(brs, 1H); 3.32 (s, 3H); 7.33 (s, 5H).

27 (CDCI₃, 90 MHz, ¹H) δ 1.22 (s, 3H); 1.3-2.3 (m, 10H); 2.72

(brs, 1H); 3.39 (d, 1H, J=7.5Hz); 3.88 (s, 3H); 7.34 (s, 5H).

28 (CDCI₃, 90 MHz, ¹H) δ 1.31 (s, 3H); 1.1-2.2 (m, 10H); 3.10

(t, 1H, J=3Hz); 3.36 (s, 3H); 4.51 (d, 1H, J=12Hz); 4.73 (d, 1H, J=12Hz); 7.1-7.4 (m, 3H); 7.5-7.7 (m, 1H).

29 (CDCI₃, 90 MHz, ¹H) δ 1.17 (t, 3H, J=7.5Hz); 1.30 (s, 3H);

1.1-2.2 (m, 10H); 3.09 (t, 1H, J=3Hz); 3.66 (q, 2H,

J=7.5Hz); 4.50 (d, 1H, J=12.5Hz); 4.74 (d, 1H, J=12.5Hz); 7.1-7.4 (m, 3H); 7.5-7.7 (m, 1H).

30 (CDCI₃, 90 MHz, ¹H) δ 1.28 (s, 3H); 1.1-2.1 (m, 10H); 3.00

(brs, 1H); 7.35 (s, 5H).

31 (CDCI₃, 90 MHz, ¹H) δ 1.32 (s, 3H); 1.1-2.4 (m, 16H); 3.00

(brs, 1H); 3.1-4.0 (m, 6H).

32 (CDCI₃, 90 MHz, ¹H) δ 1.28 (s, 3H); 1.2-2.7 (m, 16H); 3.00

(brs, 1H); 3.33 (s, 3H); 3.2-3.7 (m, 3H); 3.8-4.2 (m, 2H).

33 (CDCI₃, 90 MHz, ¹H) δ 1.17 (t, 3H, J=7.5Hz); 1.27 (s, 3H);

1.1-2.5 (m, 16H); 3.00 (brs, 1H); 3.2-4.2 (m, 7H).

34 (CDCI₃, 90 MHz, ¹H) δ 1.18 (s, 3H); 1.3-2.3 (m, 10H); 2.67

(s, 1H); 3.39 (d, 1H, J=7.5Hz); 3.91 (s, 4H); 4.62 (d, 1H, J=12Hz); 4.80 (d, 1H, J=12Hz); 6.9-7.4 (m, 3H).

35 (CDCI₃, 90 MHz, ¹H) δ 1.22 (s, 3H); 1.3-2.4 (m, 10H); 2.76

(s, 1H); 3.00 (m, 1H); 3.90 (s, 4H); 4.68 (d, 1H, J=10.5Hz); 4.92 (d, 1H, J=10.5Hz); 7.1-7.45 (m, 3H). 36 (CDCI₃, 90 MHz, ¹H) δ 1.22 (s, 3H); 1.3-2.3 (m, 10H); 3.00 (brs, 1H); 3.36 (s, 1H); 4.55 (d, 1H, J=10.5Hz); 4.78 (d, 1H, J=10.5Hz); 6.85-7.35 (m, 3H).

37 (CDCI₃, 90 MHz, ¹H) δ 1.27 (s, 3H); 1.2-2.2 (m, 10H); 3.03

(brs, 1H); 3.25 (brs, 1H); 4.65 (d, 1H, J=10.5Hz); 4.85 (d, 1H, J=10.5Hz); 7.0-7.4 (m, 3H).

38 (CDCI₃, 200 MHz, ¹H) δ 1.27 (s, 3H); 1.3-2.2 (m, 10H);

3.06 (t, 1H, J=3Hz); 3.32 (s, 3H); 4^64 (d, 1H, J=10.2Hz); 4.84 (d, 1H, J=10.1Hz); 7.1-7.3 (m, 3H).

39 (CDCI₃, 200 MHz, ¹H) δ 1.15 (t, 3H, J=7.5Hz); 1.25 (s,

3H); 1.3-2.2 (m, 10H); 3.06 (t, 1H, J=3.1Hz); 3.63 (qd, 2H, J=1.2,7.1Hz); 4.64 (d, 1H, J=10.1Hz); 4.85 (d, 1H,

J=10.1Hz); 7.1-7.3 (m, 3H).

40 (CDCI₃, 90 MHz, ¹H) δ 1.23 (s, 3H); 1.3-2.2 (m, 10H); 3.02

(brs, 1H); 3.32 (s, 3H); 4.55 (dd, 1H, J=2,10Hz); 4.77 (dd, 1H, J=2,10Hz); 6.8-7.3 (m, 3H).

41 (CDCI₃, 90 MHz, ¹H) δ 1.10 (t, 3H, J=7.5Hz); 1.23 (s, 3H);

1.3-2.2 (m, 10H); 3.02 (brs, 1H); 3.63 (q, 2H, J=7.5Hz); 4.57 (dd, 1H, J=2,10Hz); 4.77 (dd, 1H, J=2,10Hz); 6.8-7.3 (m, 3H).

42 (CDCI₃, 90 MHz, ¹H) δ 0.88 (td, 3H, J=2,7.5Hz); 1.1-2.3

(m, 14H); 2.57 (s, 1H); 3.35 (dd, 1H, J=2,7.5Hz); 3.88 (s, 4H); 4.35 (d, 1H, J=12Hz); 4.62 (d, 1H, J=12Hz); 7.35 (s, 5H).

43 (CDCI₃, 90 MHz, ¹H) δ 0.90 (m, 3H); 1.0-2.3 (m, 14H);

3.09 (brs, 1H); 3.53 (br, 1H); 4.31 (d, 1H, J=12Hz); 4.62 (d, 1H, J=12Hz); 7.37 (s, 5H).

44 (CDCI₃, 90 MHz, ¹H) δ 0.88 (t, 3H, J=7Hz); 1.0-2.3 (m,

14H); 3.04 (t, 1H, J=3Hz); 3.38 (s, 3H); 4.37 (d, 1H, J=12Hz); 4.65 (d, 1H, J=12Hz); 7.27 (s, 5H). 45 (CDCI₃, 90 MHz, ¹H) δ 0.87 (t, 3H, J-7.5Hz); 1.17 (t, 3H,

J=7.5Hz); 1.0-2.2 (m, 14H); 3.02 (t, 1H, J=3Hz); 4.36 (d, 1H, J=12Hz); 4.63 (d, 1H, J=12Hz); 7.33 (s, 5H).

TEST A

Seeds of barley (Hordeum vulgare), bamyardgrass (Echinochloa crus-galli), cheatgrass (Bromus secalinus) , cocklebur (Xanthium pensylvanicum), cor n (Zea mays), Cotton (Gossypium hirsutum), crabgrass

(Digitaria spp.), giant foxtail (Setaria faberi), morningglory (Ipomoea spp.), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus ) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (two to three leaf stage) for postemergence treatments.

Treated plants and controls were maintained in a greenhouse for approximately fifteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

Table A COMPOUND

Rate (200 g/ha) 1 2 3 5 7 8

POSTEMERGENCE

Barley 0 9 5 2 7 7

Barnyardgrass 5 9 9 9 7 8

Cheatgrass 0 8 0 0 0 2

Cocklebur 0 0 1 1 0 2

Corn 2 9 9 1 3 6

Cotton 0 3 0 0 0 2

Crabgrass 0 9 2 2 3 4

Giant foxtail 0 9 9 4 5 4

Morningglory 0 2 0 0 0 0

Nutsedge 0 8 0 0 0 0

Rice 0 9 0 0 8 9

Sorghum 5 9 0 0 0 2

Soybean 5 6 1 1 1 1

Sugar beet 0 0 0 0 0 0

Velvetleaf 1 7 0 0 0 7

Wheat 0 9 0 0 4 8

Wild oat 0 0 0 0 0 0

Table A COMPOUND

Rate (200 g/ha) 1 2 3 5 7 8

PREEMERGENCE

Barley 0 9 1 0 9 9

Barnyardgrass 9 10 10 10 9 9

Cheatgrass 2 0 9 7 5 8

Cocklebur 0 1 0 0 - 5

Corn 2 9 5 2 3 5

Cotton 0 5 2 0 0 3

Crabgrass 7 9 10 10 9 7

Giant foxtail 3 8 10 9 3 8

Morningglory 0 2 0 0 0 0

Nutsedge 0 0 2 0 4 7

Rice 0 8 0 0 6 8

Sorghum 0 9 7 6 1 4

Soybean 0 6 0 0 1 5

Sugar beet 1 5 5 3 0 2

Velvetleaf 1 3 2 3 5 6

Wheat 3 7 1 1 8 7

Wild oat 0 1 5 1 0 0

Table A COMPOUND

Rate (50 g/ha) 1 2 3 5 7 8

POSTEMERGENCE

Barley 0 1 0 0 0 2

Barnyardgrass 0 9 9 1 0 0

Cheatgrass 0 0 0 0 0 0

Cocklebur 0 0 1 - 0 0

Corn 0 5 2 0 0 2

Cotton 0 - 0 0 0 0

Crabgrass 0 5 0 0 0 0

Giant foxtail 0 0 0 0 0 0

Morningglory 0 0 0 0 0 0

Nutsedge 0 - 0 0 2 0

Rice 0 2 0 0 0 0

Sorghum 0 0 0 0 0 0

Soybean 0 0 0 0 0 0

Sugar beet 0 0 0 0 0 0

Velvetleaf 0 0 0 0 0 0

Wheat 0 4 0 0 2 2

Wild oat 0 0 0 0 0 0

Table A COMPOUND

Rate (50 g/ha) 1 2 3 5 7 8

PREEMERGENCE

Barley 0 0 0 0 0 0

Barnyardgrass 0 9 9 9 8 2

Cheatgrass 0 0 2 4 0 0

Cocklebur 0 0 0 0 0 2

Corn 0 5 4 0 0 0

Cotton 0 2 0 0 0 0

Crabgrass 0 8 9 6 3 6

Giant foxtail 8 2 8 8 0 2

Morningglory 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 0

Rice 0 2 0 0 0 2

Sorghum 0 2 0 0 0 0

Soybean 0 0 0 0 0 0

Sugar beet 0 3 3 0 0 0

Velvetleaf 0 0 0 2 0 2

Wheat 0 7 0 0 0 0

Wild oat 0 0 0 0 0 0

TEST B

Seeds of barley (Hordeum vulgare), bamyardgrass ( Echinochloa crus-galli). bedstraw (Galium aparine), blackgrass (Alopecurus

myosuroides), cheatgrass (Bromus secalinus). chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), giant foxtail (Setaria faberii). lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea). rape (Brassica napus), rice (Oryza sativa), sorghum (Sorgh um bicolor), soybean (Glycine max), sugar beet (Beta vulgraris), velvetleaf (Abutilon theophrasti). wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments.

Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

Table B COMPOUND

Rate (2000 g/ha) 17

POSTEMERGENCE

Barley 9

Barnyardgrass 9

Bedstraw 4

Blackgrass 8

Cheatgrass 8

Chickweed -

Corn 9

Cotton 2

Crabgrass 7

Giant foxtail 4

Lambsquarters 3

Morningglory 2

Nutsedge 9

Rape 0

Rice 9

Sorghum 7

Soybean 8

Sugar beet 4

Velvetleaf 7

Wheat 9

Wild buckwheat -

Wild oat 5

Table B COMPOUND

Rate (2000 g/ha) 17

PREEMERGENCE

Barley 3

Barnyardgrass 10

Bedstraw 4

Blackgrass 9

Cheatgrass 9

Chickweed 3

Corn 9

Cotton 5

Crabgrass 9

Giant foxtail 8

Lambsquarters 5

Morningglory 0

Nutsedge 9

Rape 0

Rice 10

Sorghum 7

Soybean 6

Sugar beet 4

Velvetleaf 6

Wheat 4

Wild buckwheat 2

Wild oat 0

Table B COMPOUND

Rate (1000 g/ha) 27 34 35 42

POSTEMERGENCE

Barley 5 5 0 2

Barnyardgrass 9 7 2 8

Bedstraw 0 0 0 0

Blackgrass 5 8 3 3

Cheatgrass 2 3 0 4

Chickweed 3 0 0 0

Cocklebur - - - 3

Corn 7 2 0 2

Cotton 4 1 1 2

Crabgrass 5 2 0 0

Giant foxtail 2 0 0 0

Lambsquarters 0 0 0 0

Morningglory 1 0 0 0

Nutsedge 7 7 6 0

Rape 0 0 0 0

Rice 9 7 0 0

Sorghum 3 0 0 0

Soybean 3 2 2 2

Sugar beet 1 2 2 3

Velvetleaf 3 8 3 2

Wheat 7 0 0 1

Wild buckwheat 0 0 0 1

Wild oat 0 0 0 2

Table B COMPOUND

Rate (1000 g/ha) 27 34 35 42

PREEMERGENCE

Barley 3 1 1 0

Barnyardgrass 10 9 6 10

Bedstraw 0 0 0 0

Blackgrass 9 7 8 1

Cheatgrass 9 5 5 6

Chickweed 7 5 5 1

Cocklebur - - - 0

Corn 8 4 2 0

Cotton 2 2 0 0

Crabgrass 8 9 6 9

Giant foxtail 6 6 6 5

Lambsquarters 1 0 2 9

Morningglory 0 0 0 0

Nutsedge 4 6 6 0

Rape 1 0 0 0

Rice 9 1 1 0

Sorghum 8 2 0 0

Soybean 3 2 0 0

Sugar beet 5 3 2 3

Velvetleaf 7 7 6 2

Wheat 7 0 0 0

Wild buckwheat 2 0 0 0

Wild oat 3 5 1 0

Table B COMPOUND

Rate (400 g/ha) 17

POSTEMERGENCE

Barley 6

Barnyardgrass 7

Bedstraw 3

Blackgrass 5

Cheatgrass 4

Chickweed -

Corn 5

Cotton 0

Crabgrass 1

Giant foxtail 0

Lambsquarters 3

Morningglory 0

Nutsedge 2

Rape 0

Rice 3

Sorghum 0

Soybean 3

Sugar beet 4

Velvetleaf 0

Wheat 6

Wild buckwheat -

Wild oat 0

Table B COMPOUND

Rate (400 g/ha) 17

PREEMERGENCE

Barley 0

Barnyardgrass 9

Bedstraw 3

Blackgrass 6

Cheatgrass 5

Chickweed 3

Corn 5

Cotton 3

Crabgrass 6

Giant foxtail 1

Lambsquarters 2

Morningglory 0

Nutsedge 4

Rape 0

Rice 2

Sorghum 1

Soybean 5

Sugar beet 3

Velvetleaf 2

Wheat 2

Wild buckwheat 0

Wild oat 0

Table B COMPOUND

Rate (200 g/ha) 7 8 9 10 11 12 13 14 15 16 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38

POSTEMERGENCE

Barley 7 7 5 4 3 3 7 8 0 0 2 2 0 9 2 4 6 0 4 4 3 2 0 0 0 - 4 2 0

Barnyardgrass 8 9 9 8 5 9 9 9 0 0 8 9 3 9 6 8 9 2 5 0 9 0 2 2 0 0 5 1 2

Bedstraw 2 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 2 0 0 0 - 0 0 0

Blackgrass 8 9 2 3 2 0 6 8 0 2 0 0 2 7 2 3 5 0 0 0 7 2 5 0 5 - 3 2 2

Cheatgrass 0 3 0 0 0 0 3 0 0 5 0 0 0 5 0 4 4 0 2 2 3 0 0 0 0 - 2 2 2

Chickweed 3 0 2 2 0 0 0 2 7 0 2 0 0 0 0 0 0 0 2 0 0 3 0 0 0 - 0 0 0

Cocklebur 1 1 0 4 1 1 1 2 0 0 - - - - - - - - - - - - - - - - - - -

Corn 2 4 0 4 3 3 5 2 0 0 0 0 0 6 0 2 2 2 0 0 0 0 0 0 0 0 1 0 0

Cotton 0 0 0 0 0 0 0 1 0 0 0 0 2 5 2 4 0 2 2 0 0 0 0 0 0 0 0 8 1

Crabgrass 0 2 1 2 2 0 4 0 0 0 0 0 0 9 2 0 2 2 1 0 0 0 2 2 0 0 0 0 3

Giant foxtail 7 1 1 4 1 3 7 2 0 0 0 0 0 5 2 0 2 2 0 1 3 0 4 0 0 0 0 0 0

Lambsquarters 3 0 0 0 0 0 0 0 0 - 3 3 1 2 0 0 0 0 0 0 0 2 - 0 0 - 0 0 0

Morningglory 0 0 1 1 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 2 0 0 0 0 0 0 7 0 0 0 0

Rape 0 0 0 0 0 0 0 4 0 0 0 0 0 2 0 2 0 0 4 2 0 0 0 0 0 - 5 4 2

Rice 0 0 0 0 4 3 5 0 0 0 0 0 0 4 0 2 2 2 0 0 0 0 0 0 2 0 0 0 0

Sorghum 1 0 1 2 0 0 0 1 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 1 1 1 0 0 2 3 0 0 0 2 0 1 5 1 2 2 3 3 0 0 0 0 0 1 0 0 1 0

Sugar beet 0 0 0 2 0 0 0 5 4 3 2 0 2 3 6 2 2 0 2 3 0 0 0 0 0 - 4 7 2

Velvetleaf 1 3 0 2 2 1 1 3 0 0 0 7 0 2 2 0 1 2 3 1 2 0 7 0 6 1 1 5 4

Wheat 6 8 4 2 3 2 3 7 0 0 2 2 0 7 0 3 5 0 2 2 4 0 0 0 0 - 0 4 0

Wild buckwheat 0 1 0 2 0 0 0 2 2 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 - 0 0 0

Wild oat 1 5 0 0 0 0 0 6 0 0 0 0 0 6 0 0 3 0 2 0 2 0 0 0 0 - 0 2 0

Table B COMPOUND

Rate (200 g/ha) 39 40 41 42 43 44 45

POSTEMERGENCE

Barley 0 0 0 0 0 0 0

Barnyardgrass 5 9 6 2 9 9 3

Bedstraw 0 1 0 0 0 2 0

Blackgrass 2 8 1 0 5 5 0

Cheatgrass 2 5 3 0 3 2 0

Chickweed 0 5 0 0 - 3 0

Cocklebur - - 1 0 - 2 -

Corn 2 0 0 0 2 6 0

Cotton 2 0 0 0 0 0 0

Crabgrass 2 0 0 0 0 0 0

Giant foxtail 0 2 2 0 1 2 0

Lambsquarters 2 3 0 0 4 2 0

Morningglory 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 - - 0

Rape 0 3 0 0 0 0 0

Rice 0 2 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0

Soybean 2 0 1 0 1 1 0

Sugar beet 1 1 0 0 2 2 0

Velvetleaf 3 2 3 0 0 2 0

Wheat 2 0 0 2 0 0 0

Wild buckwheat 0 0 0 0 2 2 0

Wild oat 2 0 0 0 0 0 0

Table B COMPOUND

Rate (200 g/ha) 7 8 9 10 11 12 13 14 15 16 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38

PREEMERGENCE

Barley 0 2 0 5 2 3 2 2 0 0 0 0 0 0 0 0 2 0 0 0 0 0 2 0 0 - 2 0 0

Barnyardgrass 10 9 9 10 10 9 9 10 0 1 9 10 10 10 10 9 9 7 10 9 10 3 10 10 6 4 9 3 9

Bedstraw 2 5 0 2 0 0 2 2 0 0 2 0 0 4 3 0 3 0 0 0 0 0 0 0 0 - 0 0 0

Blackgrass 10 9 7 10 9 10 9 9 0 0 3 3 3 9 7 7 8 2 6 8 9 0 5 2 4 - 5 0 4

Cheatgrass 3 8 6 9 9 9 8 9 0 0 0 7 2 9 9 3 7 1 3 7 8 3 6 2 0 - 2 2 2

Chickweed 10 6 0 0 0 0 0 10 4 0 7 3 0 7 5 4 9 3 8 6 6 2 0 0 0 - 5 3 2

Cocklebur 4 0 0 0 0 0 0 1 0 0 - - - - - - - - - - - - - - - -

Corn 5 2 2 0 7 0 1 1 0 0 5 1 1 0 0 2 2 0 1 0 4 0 0 0 0 0 2 0 2

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 2 9 2 2 0 - 0 0 0 0 0 0 0 0 0 1

Crabgrass 9 9 6 9 9 9 9 9 - 0 3 9 9 9 9 5 9 0 9 8 9 0 10 10 3 2 7 0 9

Giant foxtail 10 9 0 10 9 9 9 9 0 0 2 9 9 9 8 0 9 0 8 5 8 3 10 6 5 0 5 2 9

Lambsquarters 8 8 0 8 7 8 8 7 3 0 0 5 0 8 10 0 8 2 6 4 9 0 0 0 0 - 0 0 2

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0

Nutsedge 5 8 0 0 0 0 0 10 0 0 0 0 0 0 0 3 4 0 0 0 3 0 0 - 2 0 - 0 0

Rape 0 0 0 0 0 0 0 0 0 0 0 2 2 2 0 0 2 0 2 2 2 0 0 0 0 - 3 0 0

Rice 0 0 0 0 0 0 0 0 0 2 0 0 0 2 2 0 0 1 4 0 2 0 0 1 0 0 0 0 1

Sorghum 2 0 2 1 0 0 4 0 0 0 0 1 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0

Soybean 0 0 2 0 0 0 0 0 0 0 0 0 0 2 2 1 1 2 2 0 0 1 1 0 0 0 2 0 0

Sugar beet 2 5 0 3 5 2 3 3 0 0 2 4 2 5 3 2 4 0 4 2 3 0 0 0 0 - 3 3 1

Velvetleaf 3 5 3 6 6 6 7 5 0 0 4 1 2 7 4 2 4 1 2 6 6 0 2 0 5 1 5 2 2

Wheat 0 4 5 8 2 4 2 3 2 0 0 0 0 2 2 0 4 0 2 0 8 2 2 0 0 - 2 0 0

Wild buckwheat 3 2 0 0 0 0 0 0 0 0 4 0 0 2 0 0 2 0 0 2 3 3 0 0 0 - 0 2 0

Wild oat 0 8 0 7 3 4 2 2 0 0 0 2 0 8 2 0 7 0 3 2 3 2 0 0 0 - 2 0 0

Table B COMPOUND

Rate (200 g/ha) 39 40 41 42 43 44 45

PREEMERGENCE

Barley 0 2 0 0 0 0 0

Barnyardgrass 9 10 10 9 10 10 10

Bedstraw 0 5 1 0 0 0 0

Blackgrass 5 7 9 6 3 9 4

Cheatgrass 2 5 5 3 3 9 5

Chickweed 0 5 - 3 0 5 3

Cocklebur - - - 0 - - -

Corn 0 2 0 0 0 9 0

Cotton 0 0 8 0 0 0 0

Crabgrass 9 9 9 3 8 10 9

Giant foxtail 8 9 9 5 4 10 8

Lambsquarters 2 5 2 0 2 2 3

Morningglory 0 0 2 0 0 0 0

Nutsedge 0 0 0 0 8 0 0

Rape 0 1 0 0 0 0 0

Rice 0 0 0 0 0 0 0

Sorghum 0 2 4 0 0 0 0

Soybean 0 0 0 0 0 0 0

Sugar beet 3 5 5 0 0 1 1

Velvetleaf 3 7 6 0 2 3 0

Wheat 0 0 0 0 0 0 0

Wild buckwheat 0 0 0 0 2 0 0

Wild oat 0 5 4 0 0 5 0

Table B COMPOUND

Rate (50 g/ha) 7 8 9 10 11 12 13 14 15 16 20 21 22 23 24 25 2628 29 30 31 32 33 36 37 38 39 40 41

POSTEMERGENCE

Barley 1 0 0 0 0 0 0 4 0 0 0 0 0 2 0 0 4 0 2 0 0 0 0 0 3 0 0 0 0

Barnyardgrass 1 9 0 5 0 2 2 6 0 0 3 2 0 6 2 0 0 2 0 0 0 0 0 0 0 1 0 8 6

Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Blackgrass 1 2 0 0 0 0 0 0 0 0 0 0 0 2 0 0 2 0 0 2 0 0 0 2 - 0 0 1 0

Cheatgrass 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0

Chickweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Cocklebur 1 1 0 - 0 0 1 0 0 0 - - - - - - - - - - - - - - 0 0

Corn 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 2 1 0 0 6 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 4 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0

Giant foxtail 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Lambsquarters 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - - 0 0

Rape 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0 1 0 0 1 0 2 1 1 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 0 0 0 0 0 0 0 3 3 0 2 0 2 0 2 2 0 2 3 0 0 0 0 - 5 0 0 0 0

Velvetleaf 0 1 0 0 0 0 0 1 0 0 0 0 0 1 2 0 0 2 0 1 0 0 0 2 3 2 1 2 0

Wheat 2 1 0 0 0 0 2 2 0 0 0 0 0 0 0 0 2 0 0 3 0 0 0 0 0 0 0 0 0

Wild buckwheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild oat 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0

Table B COMPOUND

Rate (50 g/ha) 42 43 44 45

POSTEMERGENCE

Barley - 0 0 0

Barnyardgrass - 0 3 0

Bedstraw - 0 0 0

Blackgrass - 2 0 0

Cheatgrass - 0 0 0

Chickweed - 0 0 0

Cocklebur - - 1 -

Corn - 0 0 0

Cotton - 0 0 0

Crabgrass - 0 0 0

Giant foxtail - 0 2 0

Lambsquarters - 0 0 0

Morningglory - 0 0 0

Nutsedge - - 0 0

Rape - 0 0 0

Rice - 0 0 0

Sorghum - 0 0 0

Soybean - 0 0 0

Sugar beet - 1 0 0

Velvetleaf - 0 0 0

Wheat - 0 0 0

Wild buckwheat - 0 0 0

Wild oat - 0 0 0

Table B COMPOUND

Rate (50 g/ha) 7 8 9 10 11 12 13 14 15 16 20 21 22 23 24 25 26 28 29 30 31 32 33 36 37 38 39 40 41

Barley 0 0 0 3 2 0 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Barnyardgrass 8 9 6 8 7 8 8 9 0 0 2 9 3 9 6 2 9 9 9 10 0 10 2 2 0 8 5 9 9

Bedstraw 2 0 0 0 0 0 0 0 0 0 0 0 0 - 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Blackgrass 2 7 3 9 8 5 9 4 0 0 0 0 2 8 2 2 7 2 4 7 0 0 0 0 0 0 0 5 5

Cheatgrass 0 5 2 2 3 0 5 2 0 0 0 2 0 7 3 0 2 0 2 2 0 0 0 0 0 0 0 1 2

Chickweed 0 0 0 0 0 0 0 5 0 0 0 0 0 6 0 3 7 0 0 3 0 0 0 4 2 0 0 0 -

Cocklebur 0 0 0 0 0 0 0 - 0 0 - - - - - - - - - - - - - - - -

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 1 0 0 0 0 0 0 0 0 0 0 0 0

Cotton 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass 9 9 1 9 5 8 9 9 0 0 2 5 0 9 7 0 9 7 2 8 0 7 2 2 0 9 8 9 9

Giant foxtail 9 8 0 9 7 7 8 9 0 0 1 8 3 8 3 0 5 2 3 7 0 7 4 1 0 6 6 8 6

Lambsquarters 8 7 0 3 0 0 7 3 0 0 0 - 0 8 0 0 7 0 0 2 0 0 0 0 0 0 0 2 0

Morningglory 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Nutsedge 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Rape 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 2 2 0 0 0 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 0 0 1 0 0 0 0 0 0 0 0 0 0 0

Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0

Sugar beet 0 0 0 2 0 0 0 0 0 0 0 2 2 2 2 2 2 2 2 2 0 0 0 2 2 0 0 0 0

Velvetleaf 1 2 0 3 0 1 5 0 0 0 3 0 0 2 2 1 2 2 2 0 0 0 0 2 0 1 1 5 6

Wheat 0 0 0 3 2 2 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wild buckwheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 2 2 0 0 0 0 0 0 0 0

Wild oat 0 2 0 0 2 0 0 0 0 0 0 0 0 3 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0

Table B COMPOUND

Rate (50 g/ha) 42 43 44 45

PREEMERGENCE

Barley 0 0 0 0

Barnyardgrass 2 6 9 7

Bedstraw 0 0 0 0

Blackgrass 4 2 7 2

Cheatgrass 0 2 4 0

Chickweed 0 0 0 0

Cocklebur - 0 - 0

Corn 0 0 0 0

Cotton 0 0 0 0

Crabgrass 0 2 7 0

Giant foxtail 0 2 9 3

Lambsquarters 0 0 0 0

Morningglory 0 0 0 0

Nutsedge - 3 0 0

Rape 0 0 0 0

Rice 0 0 0 0

Sorghum 0 0 0 0

Soybean 0 0 0 0

Sugar beet 0 0 0 0

Velvetleaf 0 0 2 0

Wheat 0 0 0 0

Wild buckwheat 0 0 - 0

Wild oat 0 0 2 0

TEST C

The compounds evaluated in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (paddy application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the paddy test. Water depth was approximately 2.5 cm for the paddy test and was maintained at this level for the duration of the test.

Plant species in the preemergence and postemergence tests consisted of barley (Hordeum vulgare), bedstraw (Galiura flparine), blackgrass (Alopecurus myosuroides). chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum). crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), duck salad (Heteranthera limosa), giant foxtail (Setaria faberii). green foxtail (Setaria viridis). jimsonweed (Datura stramonium), johnsongrass (Sorghum halpense). lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthusretroflexus), rape (Brassica napus), rice dry seed (Oryza sativa), ryegrass (Loliummul tiflor um), sicklepod (Cassia obtusifolia), sorghum (Sorghum bicolor), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua). All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the paddy test consisted of bamyardgrass (Echinochloa crus-galli), rice (Oryza sativa), and umbrella sedge (Cyperus difformis).

All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty-one days after application of the test compound. Plant response ratings, summarized in Table C, were recorded on a 0 to 10 scale where 0 is no injury and 10 is complete control. A dash (-) response means no test result.

Table C COMPOUND

Rate (250 g/ha) 2 3 4 8 13 14 23 26 32 40

POSTEMERGENCE

Barley 0 - - - - - - - - -

Barley Igri - 2 1 9 8 4 - 0 0 3

Bedstraw - 0 0 5 5 0 - 0 5 4

Blackgrass 7 8 3 8 8 9 - 9 5 5

Chickweed 4 2 3 5 5 5 - 9 6 6

Cocklebur 0 - - - - - - - - -

Corn 0 2 0 6 3 0 - 7 0 0

Cotton 0 0 0 3 2 0 - 0 2 0

Crabgrass 8 0 0 5 6 3 - 6 4 8

Downy brome 0 0 2 9 7 5 - 8 0 5

Duck salad - - - - - - - - - 4

Giant foxtail 9 0 0 6 6 0 - 8 6 6

Green foxtail 3 - - - - - - - - -

Jimsonweed 0 - - - - - - - - -

Johnsongrass 7 - - - - - - - - -

Lambsquarters 7 4 0 4 4 3 - 4 0 4

Morningglory 0 0 0 2 0 0 - 0 0 0

Nutsedge 4 - - - - - - - - -

Pigweed - 0 0 4 0 0 - 0 3 5

Rape 0 0 0 0 0 0 - 0 0 6

Rice Dry Seed 4 - - - - - - - - -

Ryegrass - 5 2 9 8 9 - 9 3 5

Sicklepod 0 - - - - - - - - -

Sorghum - 0 0 0 2 0 - 4 0 0

Soybean 0 0 0 3 3 2 - 0 0 3

Speedwell - 0 2 6 8 8 - 8 5 6

Sugar beet 3 0 0 4 0 0 - 0 0 4

Teaweed 3 - - - - - - - - -

Velvetleaf 4 6 0 6 3 0 - 4 0 3

Wheat 3 0 1 5 6 5 - 5 0 4

Wild buckwheat 0 0 3 3 0 5 - 3 0 3

Wild oat 0 0 0 8 3 3 - 0 0 4

Barny ardgrass 10 9 7 9 8 8 9 9 6 9

Rice Japonica - 7 5 9 9 7 9 8 3 8

Umbrella Sedge - 8 8 8 8 8 9 8 0 8

Table C COMPOUND

Rate (250 g/ha) 2 3 4 8 13 14 23 26 32 40

PREEMERGENCE

Barley 6 - - - - - - - - -

Barley Igri - 0 0 9 6 8 - 5 4 3

Bedstraw - 0 4 9 8 10 - 10 8 6

Blackgrass 6 9 7 10 10 10 - 10 5 9

Chickweed 8 7 6 9 9 9 - 10 4 8

Cocklebur 6 - - - - - - - - -

Corn 5 0 2 7 5 0 - 4 3 0

Cotton 0 4 0 5 5 2 - 5 5 6

Crabgrass 10 9 9 10 10 10 - 10 10 9

Downy brome 0 0 0 8 7 8 - 9 7 5

Duck salad - - - - - - - - - -

Giant foxtail 9 9 9 9 9 10 - 9 9 8

Green foxtail 10 - - - - - - - - -

Jimsonweed 4 - - - - - - - - -

Johnsongrass 10 - - - - - - - - -

Lambsquarters 7 10 3 9 8 8 - 9 5 10

Morningglory - 0 0 0 0 0 - 0 0 0

Nutsedge 2 - - - - - - - - -

Pigweed - 5 3 5 8 6 - 8 8 0

Rape 0 3 0 0 0 0 - 0 0 0

Rice Dry Seed 3 - - - - - - - - -

Ryegrass - 7 7 10 10 10 - 10 7 8

Sicklepod 3 - - - - - - - - -

Sorghum - 2 3 5 7 2 - 6 3 2

Soybean 0 0 0 2 3 0 - 2 0 0

Speedwell - 8 9 9 9 9 - 9 9 8

Sugar beet 6 0 3 7 5 6 - 3 2 7

Teaweed 9 - - - - - - - - -

Velvetleaf 9 7 2 7 7 7 - 7 7 8

Wheat 6 0 0 9 5 6 - 5 7 3

Wild buckwheat 4 5 5 3 2 7 - 5 6 3

Wild oat 1 0 0 7 4 7 - 4 0 0

Barnyardgrass 10 - - - - - - - - -

Rice Japonica - - - - - - - - - -

Umbrella Sedge - - - - - - - - - -

Table C COMPOUND

Rate (125 g/ha) 2 3 4 8 13 14 23 26 32 40

POSTEMERGENCE

Barley Igri 5 0 0 9 6 2 - 0 0 0

Bedstraw 5 0 0 4 0 0 - 0 0 0

Blackgrass 5 6 2 8 7 7 - 9 0 4

Chickweed 5 0 0 5 5 2 - 9 3 3

Corn 0 0 0 4 2 0 - 5 0 0

Cotton 0 0 0 0 2 0 - 0 0 0

Crabgrass 0 0 0 4 4 2 - 4 3 6

Downy brome 2 0 0 7 6 2 - 4 0 3

Duck salad - - - - - - - - - 2

Giant foxtail 2 0 0 5 4 0 - 6 5 6

Lambsquarters 0 3 0 4 4 3 - 0 0 3

Morningglory 0 0 0 2 0 0 - 0 0 0

Pigweed 0 0 0 0 0 0 - 0 0 3

Rape 0 0 0 0 0 0 - 0 0 3

Ryegrass 5 3 2 9 8 6 - 6 0 4

Sorghum 0 0 0 0 0 0 - 2 0 0

Soybean 0 0 0 2 2 0 - 0 0 0

Speedwell 0 0 0 6 6 5 - 7 3 3

Sugar beet 0 0 0 3 0 0 - 0 0 3

Velvetleaf 2 3 0 4 2 0 - 3 0 2

Wheat 6 0 0 5 5 4 - 5 0 3

Wild buckwheat 0 0 0 2 0 2 - 0 0 0

Wild oat 0 0 0 7 2 0 - 0 0 0

Barnyardgrass 9 8 7 9 7 7 8 9 6 9

Rice Japonica 7 4 1 9 8 6 8 8 0 5

Umbrella Sedge 9 8 7 8 8 8 8 8 0 8 Table C COMPOUND

Rate (125 g/ha) 2 3 4 8 13 14 23 26 32 40

PREEMERGENCE

Barley Igri 0 0 0 7 4 6 - 0 3 0

Bedstraw 3 0 3 8 8 5 - 9 8 4

Blackgrass 6 5 5 9 10 8 - 10 4 8

Chickweed 8 6 3 9 9 9 - 10 4 7

Corn 3 0 0 5 3 0 - 4 2 0

Cotton 2 4 0 5 2 0 - 5 4 1

Crabgrass 9 9 9 10 9 10 - 9 10 9

Downy brome 0 0 0 6 6 6 - 6 3 3

Duck salad - - - - - - - - - -

Giant foxtail 9 9 7 9 9 9 - 9 8 7

Lambsquarters 10 10 3 8 6 7 - 8 5 10

Morningglory 0 0 0 0 0 0 - 0 0 0

Pigweed 3 5 2 5 5 5 - 7 7 0

Rape 0 0 0 0 0 0 - 0 0 0

Ryegrass 4 4 4 10 9 10 - 10 4 8

Sorghum 3 0 0 4 6 0 - 4 2 0

Soybean 2 0 0 1 0 0 - 0 0 0

Speedwell - 7 7 8 8 9 - 9 9 8

Sugar beet 5 0 0 5 5 6 - 2 1 6

Velvetleaf 7 4 0 6 5 6 - 7 6 7

Wheat 4 0 0 7 5 5 - 3 5 0

Wild buckwheat 0 5 4 - 0 7 - 5 3 3

Wild oat 0 0 0 4 3 4 - 3 0 0

Barnyardgrass - - - - - - - - - -

Rice Japonica - - - - - - - - - -

Umbrella Sedge - - - - - - - - - - Table C COMPOUND

Rate (62 g/ha) 2 3 4 8 13 14 23 26 32 40

POSTEMERGENCE

Barley 0 - - - - - - - - -

Barley Igri 2 0 0 8 5 0 - 0 0 0

Bedstraw 3 0 0 3 0 0 - 0 0 0

Blackgrass 5 2 0 8 7 5 - 8 0 3

Chickweed 4 0 0 5 5 2 - 6 0 0

Cocklebur 0 - - - - - - - - -

Com 0 0 0 2 0 0 - 3 0 0

Cotton 0 0 0 0 0 0 - 0 0 0

Crabgrass 0 0 0 3 2 0 - 4 2 5

Downy brome 0 0 0 5 5 2 - 0 0 0

Duck salad - - - - - - - - - 0

Giant foxtail 0 0 0 4 3 0 - 4 3 5

Green foxtail 0 - - - - - - - - -

Jimsonweed 0 - - - - - - - - -

Johnsongrass 0 - - - - - - - - -

Lambsquarters 0 0 0 3 3 0 - - 0 2

Morningglory 0 0 0 0 0 0 - 0 0 0

Nutsedge 0 - - - - - - - - -

Pigweed 0 0 0 0 0 0 - 0 0 0

Rape 0 0 0 0 0 0 - 0 0 0

Rice Dry Seed 0 - - - - - - - - -

Ryegrass 5 0 0 8 5 4 - 6 0 3

Sicklepod 0 - - - - - - - - -

Sorghum 0 0 0 0 0 0 - 0 0 0

Soybean 0 0 0 0 0 0 - 0 0 0

Speedwell 0 0 0 6 6 4 - 7 0 0

Sugar beet 3 0 0 0 0 0 - 0 0 0

Teaweed 0 - - - - - - - - -

Velvetleaf 0 0 0 0 0 0 - 2 0 0

Wheat 3 0 0 5 4 2 - 3 0 0

Wild buckwheat 0 0 0 0 - 0 - 0 0 0

Wild oat 0 0 0 4 0 0 - 0 0 0

Bamyardgrass 7 6 5 6 5 6 8 6 5 9

Rice Japonica 6 0 1 7 6 2 7 2 0 1

Umbrella Sedge 7 4 6 7 8 7 8 7 0 6

Table C COMPOUND

Rate (62 g/ha) 2 3 4 8 13 14 23 26 32 40

PREEMERGENCE

Barley 0 - - - - - - - - -

Barley Igri 0 0 0 4 3 5 - 0 0 0

Bedstraw 0 0 3 7 7 5 - 9 2 3

Blackgrass 4 3 0 9 9 4 - 9 0 6

Chickweed 8 6 2 8 8 8 - 4 0 6

Cocklebur 0 - - - - - - - - -

Corn 2 0 0 4 0 0 - 3 0 0

Cotton 2 2 0 3 2 0 - 0 3 0

Crabgrass 8 8 6 10 9 9 - 9 8 9

Downy brome 0 0 0 0 0 5 - 2 0 0

Duck salad - - - - - - - - - -

Giant foxtail 7 8 5 9 8 8 - 7 7 5

Green foxtail 0 - - - - - - - - -

Jimsonweed 0 - - - - - - - - -

Johnsongrass 0 - - - - - - - - -

Lambsquarters 10 10 0 6 4 5 - 7 0 10

Morningglory 0 0 0 0 0 0 - 0 0 0

Nutsedge 2 - - - - - - - - -

Pigweed 2 3 0 3 3 4 - 6 3 0

Rape 0 0 0 0 0 0 - 0 0 0

Rice Dry Seed 0 - - - - - - - - -

Ryegrass 3 3 3 8 9 8 - 9 0 6

Sicklepod 3 - - - - - - - - -

Sorghum 2 0 0 2 2 0 - 2 0 0

Soybean 0 0 0 0 0 0 - 0 0 0

Speedwell - 7 7 7 6 8 - 2 - 8

Sugar beet 5 0 0 4 3 4 - 1 0 5

Teaweed 8 - - - - - - - - -

Velvetleaf 5 4 0 5 4 4 - 4 3 6

Wheat 3 0 0 5 4 4 - 3 1 0

Wild buckwheat 0 5 0 0 0 2 - 4 0 0

Wild oat 0 0 0 2 1 0 - 0 0 0

Barnyardgrass 8 - - - - - - - - -

Rice Japonica - - - - - - - - - -

Umbrella Sedge - - - - - - - - - -

Table C COMPOUND

Rate (31 g/ha) 2 3 4 8 13 14 23 26 32 40

POSTEMERGENCE

Barley Igri 0 0 5 3 0 - 0 0 0

Bedstraw 0 0 0 0 0 0 - - 0 0

Blackgrass 3 0 0 3 4 0 - 8 0 0

Chickweed 3 0 0 1 4 0 - 6 0 0

Corn 0 0 0 2 0 0 - 0 0 0

Cotton 0 0 0 0 0 0 - 0 0 0

Crabgrass 0 0 0 0 0 0 - 3 0 3

Downy brome 0 0 0 0 4 0 - 0 0 0

Duck salad - - - - - - - - - 0

Giant foxtail 0 0 0 0 2 0 - 1 0 0

Lambsquarters 0 0 0 0 - - - 0 0 0

Morningglory 0 0 0 0 0 0 - 0 0 0

Pigweed 0 0 0 0 0 0 - 0 0 0

Rape 0 0 0 0 0 0 - 0 0 0

Ryegrass 0 0 0 6 3 4 - 4 0 0

Sorghum 0 0 0 0 0 0 - 0 0 0

Soybean 0 0 0 0 0 0 - 0 0 0

Speedwell 0 0 0 5 5 3 - 7 0 0

Sugar beet 0 0 0 0 0 0 - 0 0 0

Velvetleaf 0 0 0 0 0 0 - 0 0 0

Wheat 0 0 0 4 2 0 - 0 0 0

Wild buckwheat 0 0 0 0 0 0 - 0 0 0

Wild oat 0 0 0 0 0 0 - 0 0 0

Barnyardgrass 5 4 4 5 4 5 7 5 4 6

Rice Japonica 1 0 0 3 2 2 5 0 0 0

Umbrella Sedge 1 4 4 4 2 5 8 5 0 5 Table C COMPOUND

Rate (31 g/ha) 2 3 4 8 13 14 23 26 32 40

PREEMERGENCE

Barley Igri 0 0 0 2 0 4 - 0 0 0

Bedstraw 0 0 0 7 6 4 - 0 0 0

Blackgrass 0 0 0 7 6 6 - 6 0 3

Chickweed 7 5 0 7 5 5 - 3 0 4

Corn 0 0 0 3 0 0 - 0 0 0

Cotton 0 0 0 2 2 0 - 0 - 0

Crabgrass 4 7 6 9 8 9 - 8 8 7

Downy brome 0 0 0 0 0 5 - 0 0 0

Duck salad - - - - - - - - - -

Giant foxtail 2 7 3 9 7 7 - 7 3 2

Lambsquarters 10 3 0 6 3 5 - 0 0 5

Morningglory 0 0 0 0 0 0 - 0 0 0

Pigweed 0 0 0 3 2 0 - 6 0 0

Rape 0 0 0 0 0 0 - 0 0 0

Ryegrass 0 0 0 7 3 6 - 5 0 3

Sorghum 0 0 0 2 0 0 - 0 0 0

Soybean 0 0 0 0 0 0 - 0 0 0

Speedwell - 6 5 6 5 5 - 0 8 7

Sugar beet 5 0 0 3 1 2 - 0 0 3

Velvetleaf 3 2 0 4 3 3 - 3 0 2

Wheat 2 0 0 4 3 2 - 3 0 0

Wild buckwheat 0 5 0 0 0 0 - 0 0 0

Wild oat 0 0 0 0 0 0 - 0 0 0

Barnyardgrass - - - - - - - - - -

Rice Japonica - - - - - - - - - -

Umbrella Sedge - - - - - - - - - - Table C COMPOUND

Rate (16 g/ha) 2 3 4 8 13 14 23 26 32 40

POSTEMERGENCE

Barley 0 - - - - - - - - -

Barley Igri 0 0 0 2 3 0 - 0 0 0

Bedstraw 0 0 0 0 0 0 - 0 0 0

Blackgrass 0 0 0 0 4 0 - 0 0 0

Chickweed 0 0 0 0 4 0 - 0 0 0

Cocklebur 0 - - - - - - - - -

Corn 0 0 0 0 0 0 - 0 0 0

Cotton 0 0 0 0 0 0 - 0 0 0

Crabgrass 0 0 0 0 0 0 - 0 0 0

Downy brome 0 0 0 0 0 0 - 0 0 0

Duck salad - - - - - - - - - 0

Giant foxtail 0 0 0 0 0 0 - 0 0 0

Green foxtail 0 - - - - - - - - -

Jimsonweed 0 - - - - - - - - -

Johnsongrass 0 - - - - - - - - -

Lambsquarters 0 0 0 - 1 0 - 0 0 0

Morningglory 0 0 0 0 0 0 - 0 0 0

Nutsedge 0 - - - - - - - - -

Pigweed 0 0 0 0 0 0 - 0 0 0

Rape 0 0 0 0 0 0 - 0 0 0

Rice Dry Seed 0 - - - - - - - - -

Ryegrass 0 0 0 5 0 0 - 0 0 0

Sicklepod 0 - - - - - - - - -

Sorghum 0 0 0 0 0 0 - 0 0 0

Soybean 0 0 0 0 0 0 - 0 0 0

Speedwell 0 0 0 2 5 3 - - 0 0

Sugar beet 0 0 0 0 0 0 - 0 0 0

Teaweed 0 - - - - - - - - -

Velvetleaf 0 0 0 0 0 0 - 0 0 0

Wheat 0 0 0 0 0 0 - 0 0 0

Wild buckwheat 0 0 0 0 0 0 - 0 0 0

Wild oat 0 0 0 0 0 0 - 0 0 0

Bamyardgrass 5 4 3 4 3 4 5 5 0 6

Rice Japonica 0 0 0 1 0 2 0 0 0 0

Umbrella Sedge 0 0 2 0 0 4 5 0 0 3

Table C COMPOUND

Rate (16 g/ha) 2 3 4 8 13 14 23 26 32 40

PREEMERGENCE

Barley 0 - - - - - - - - -

Barley Igri 0 0 0 0 0 0 - 0 0 0

Bedstraw 0 0 0 5 4 0 - 0 0 0

Blackgrass 0 0 0 5 4 4 - 0 0 0

Chickweed 7 3 0 6 0 5 - 0 0 3

Cocklebur 0 - - - - - - - - -

Corn 0 0 0 2 0 0 - 0 0 0

Cotton 0 0 0 1 0 0 - 0 0 0

Crabgrass 2 4 3 7 7 7 - 7 7 2

Downy brome 0 0 0 0 0 2 - 0 0 0

Duck salad

Giant foxtail 0 4 2 7 7 6 - 4 0 0

Green foxtail 0 - - - - - - - - -

Jimsonweed 0 - - - - - - - - -

Johnsongrass 0 - - - - - - - - -

Lambsquarters 10 3 0 3 0 5 - 0 0 3

Morningglory 0 0 0 0 0 0 - 0 0 0

Nutsedge 0 - - - - - - - - -

Pigweed 0 0 0 0 0 0 - 0 0 0

Rape 0 0 0 0 0 0 - 0 0 0

Rice Dry Seed 0 - - - - - - - - -

Ryegrass 0 0 0 0 0 4 - 0 0 0

Sicklepod

Sorghum 0 0 0 0 0 0 - 0 0 0

Soybean 0 0 0 0 0 0 - 0 0 0

Speedwell - 3 3 5 4 5 - 0 3 5

Sugar beet 4 0 0 2 0 - - 0 0 0

Teaweed 2 - - - - - - - - -

Velvetleaf 0 0 0 2 2 0 - 0 0 0

Wheat 0 0 0 4 3 0 - 0 0 0

Wild buckwheat 0 3 0 0 0 0 - 0 0 0

Wild oat 0 0 0 0 0 0 - 0 0 0

Barnyardgrass 3 - - - - - - - - -

Rice Japonica - - - - - - - - - -

Umbrella Sedge - - - - - - - - - - -

Table C COMPOUND

Rate (4 g/ha) 2

POSTEMERGENCE

Barley 0

Blackgrass 0

Chickweed 0

Cocklebur 0

Corn 0

Cotton 0

Crabgrass 0

Downy brome 0

Giant foxtail 0

Green foxtail 0

Jimsonweed 0

Johnsongrass 0

Lambsquarters 0

Morningglory 0

Nutsedge 0

Rape 0

Rice Dry Seed 0

Sicklepod 0

Soybean 0

Sugar beet 0

Teaweed 0

Velvetleaf 0

Wheat 0

Wild buckwheat 0

Wild oat 0

Barnyardgrass 0 Table C COMPOUND

Rate (4 g/ha) 2

PREEMERGENCE

Barley 0

Blackgrass 0

Chickweed 0

Cocklebur 0

Corn 0

Cotton 0

Crabgrass 0

Downy brome 0

Giant foxtail 0

Green foxtail 0

Jimsonweed 0

Johnsongrass 0

Lambsquarters 0

Morningglory

Nutsedge 0

Rape 0

Rice Dry Seed 0

Sicklepod 0

Soybean 0

Sugar beet 0

Teaweed 2

Velvetleaf 0

Wheat 0

Wild buckwheat 0

Wild oat 0

Barnyardgrass 0 TESTD

Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Japonica rice (Oryza sativa) seedlings at the 2.0 to 2.5 leaf stage, seeds selected from bamyardgrass (Echinochloa crusgalli), duck salad (Heteranthera limosa), umbrella sedge (Cyperus difformis). and tubers selected from arrowhead (Sagittaria spp.), waterchestnut (Eleocharis spp.), were planted into this soil. After planting, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent and applied directly to the paddy water. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table D, are reported on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

Table D COMPOUND

Rate (500 g/ha) 1 2 3 4 5 6 9 10 11 20 28

PADDY

Arrowhead 5 8 9 3 2 3 0 2 0 0 0

Barnyardgrass 9 10 10 9 8 8 8 10 10 6 8

Duck salad 10 10 10 10 10 10 10 10 10 10 7

Japonica rice 7 7 4 2 6 8 6 4 4 3 2

Umbrella sedge 9 10 10 10 9 9 8 10 10 9 9

Waterchestnut 5 8 4 5 5 4 3 3 1 3 2

Rate (250 g/ha) 1 2 3 4 5 6 9 10 11 20 28 PADDY

Arrowhead 4 7 4 1 2 3 0 2 0 0 0

Barnyardgrass 7 10 10 8 6 7 6 8 9 3 7

Duck salad 10 10 10 10 10 10 10 10 5 10 7

Japonica rice 5 6 2 0 4 7 4 2 3 2 0

Umbrella sedge 9 10 9 10 9 9 7 9 9 7 9

Waterchestnut 3 7 4 4 4 4 3 0 0 2 2

Rate (125 g/ha) 1 2 3 4 5 6 9 10 11 20 28

PADDY

Arrowhead 2 3 3 0 0 0 0 2 0 0 0

Barnyardgrass 6 8 8 9 5 6 5 8 7 3 7

Duck salad 10 10 10 7 10 10 3 7 - 7 7

Japonica rice 2 5 2 0 2 4 2 1 2 1 0

Umbrella sedge 9 10 9 9 8 9 5 9 - 6 6

Waterchestnut 3 4 4 3 1 3 0 0 0 0 0

Table D COMPOUND

Rate (64 g/ha) 1 2 3 4 5 6 9 10 11 20 28

PADDY

Arrowhead 0 3 1 0 0 0 0 0 0 0 0

Barnyardgrass 5 8 7 7 4 5 3 7 6 1 6

Duck salad 10 10 10 5 10 9 3 5 4 3 7

Japonica rice 1 3 2 0 1 3 0 0 2 0 0

Umbrella sedge 8 10 9 9 6 8 5 6 6 5 5

Waterchestnut 2 3 3 3 1 3 0 0 0 0 0

Rate (32 g/ha) 1 2 3 4 5 6 9 10 11 20 28

PADDY

Arrowhead 0 1 1 0 0 0 0 0 0 0 0

Barnyardgrass 3 6 7 2 3 4 1 6 5 0 4

Duck salad 8 10 9 4 10 8 2 4 0 0 2

Japonica rice 0 2 1 0 0 0 0 0 0 0 0

Umbrella sedge 4 9 9 7 4 8 3 6 5 1 4

Waterchestnut 0 4 2 0 0 2 0 0 0 0 0

TEST E

Plastic pots were partially filled with silt loam soil. The soil was then flooded with water and Japonica rice (Oryza sativa) sprouted seeds and 1.5 leaf transplants were planted in the soil. Seeds of bamyardgrass (Echinochloa crus-galli) were planted in saturated soil and plants grown to the 1 leaf and 2 leaf stages for testing. At testing, the water level for all plantings was raised to 2 cm above the soil surface. Chemical treatments were formulated in a non-phytotoxic solvent and applied directly to the paddy water. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarize in Table E are reported on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

Table E COMPOUND

Rate (1000 g/ha) 2 4 7 8 9 10 13 14 15 26 27 28 29 30 31 32 34 35 36

Flood

1-LF B.Y. Grass 10 10 7 8 9 9 9 9 10 8 10 10 9 9 9 9 9 9 10

2-LF B.Y. Grass 9 9 6 7 9 6 7 6 6 6 9 8 6 6 5 6 7 7 7

Jap Direct Seed 10 9 9 9 9 9 9 9 9 8 9 8 9 9 9 9 8 9 9

Jap Rice Eff 9 4 9 8 9 8 6 7 7 7 7 6 9 7 8 7 5 5 9

Rate (500 g/ha) 4 5 7 8 9 10 13 14 15 16 17 19 26 27 28 29 30 31 32 34 35 36

Flood

1-LF B.Y. Grass 10 - 6 7 8 9 7 9 9 9 10 9 9 10 - 9 9 6 9 8 9 9 2-LF B.Y. Grass 8 6 6 6 8 6 5 6 5 7 8 10 5 8 8 5 4 4 5 8 6 6

Jap Direct Seed 7 8 9 9 9 8 8 8 8 9 9 9 7 8 8 8 8 8 8 7 7 9 Jap Rice Eff 3 5 8 8 7 7 6 5 6 8 7 9 5 6 7 8 5 6 5 4 3 7

Rate (300 g/ha) 2

Flood

1-LF B.Y. Grass 10

2-LF B.Y. Grass 9

Jap Direct Seed 9

Jap Rice Eff 8

able E COMPOUND

Rate (250 g/ha) 4 5 7 8 9 10 13 14 15 16 17 19 26 27 28 29 30 31 32 34 35 36

Flood

1-LF B.Y. Grass 10 9 5 6 7 9 6 9 9 8 8 9 4 9 10 9 8 5 9 8 5 8

2-LF B.Y. Grass 7 5 4 5 7 5 4 6 4 5 8 8 4 7 8 5 4 3 5 6 4 6

Jap Direct Seed 5 5 8 8 9 7 8 8 8 9 9 9 5 5 5 7 7 7 7 5 6 8

Jap Rice Eff 2 3 7 7 6 5 5 4 5 7 7 5 4 3 3 7 5 4 4 2 2 6

Rate (100 g/ha) 2 4 5 7 8 9 10 13 14 15 16 17 19 26 27 28 29 30 31 32 34 35 36

Flood

1-LF B.Y. Grass 8 8 3 3 5 5 8 5 7 6 6 7 8 3 7 5 6 8 4 6 5 2 8

2-LF B.Y. Grass 9 4 0 0 4 5 4 3 4 4 4 5 6 3 4 5 4 3 2 4 4 3 5

Jap Direct Seed 8 2 0 0 7 6 6 4 5 5 6 7 8 3 4 2 6 6 5 6 1 3 7

Jap Rice Eff 5 2 0 4 5 0 4 1 2 3 0 3 0 2 2 2 6 1 1 2 1 1 4

Rate (40 g/ha) 4 5 7 8 9 10 13 14 15 16 17 19 26 27 28 29 30 31 32 34 35 36

Flood

1-LF B.Y. Grass 4 0 0 4 4 4 3 5 5 2 4 8 0 4 0 5 4 3 5 5 0 5

2-LF B.Y. Grass 3 0 0 0 4 3 1 4 3 2 3 4 2 3 0 3 3 0 3 4 2 4

Jap Direct Seed 1 0 0 0 4 5 2 3 3 0 4 4 2 3 2 5 4 1 3 5 1 2

Jap Rice Eff 2 0 0 0 0 2 0 1 2 0 0 0 2 2 1 4 0 0 4 1 1 1

Table E COMPOUND

Rate (30 g/ha) 2

Flood

1-LF B.Y. Grass 5

2-LF B.Y.Grass 4

Jap Direct Seed 3

Jap Rice Eff 0

Rate (16 g/ha) 5 16 17 19

Flood

1-LF B.Y.Grass 0 0 3 4

2-LF B.Y.Grass 0 0 0 3

Jap Direct Seed 0 0 0 0

Jap Rice Eff 0 0 0 0

TEST F

Seeds of barnyardgrass (Echinochloa crus-galli), corn (Zea mays), cotton (Gossypium hirsutam), crabgrass (Dititaria sabguinalis), fall panicum (Panicum dichotomiflorum), giant foxtail (Setaria faberii), green foxtail (Setaria vividis), Johnson grass (Sorghum halepense). signalgrass (Brachiaria platvphylla). soybean (Glycine max) and wild proso (Panicum miliaceum), were planted into a silt loam soil. Test chemicals, dissolved in a non-phytotoxic solvent, were then applied to the soil surface within one day after the seeds were planted. Pots receiving these preemergence treatments were placed in the greenhouse and maintained according to routine greenhouse procedures.

Treated plants and untreated controls were maintained in the greenhouse approximately 21 days after application of the test compound. Visual evaluations of plant injury responses were then recorded. Plant response ratings, summarized in Table F, are reported on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test results.

Table F COMPOUND

Rate (250 g/ha)

PREEMERGENCE

Barnyardgrass 10

Com G4689A 8

Cotton 7

Crabgrass 9

Fall Panicum 9

Giant Foxtail 8

Green Foxtail 8

Johnson Grass 8

Signalgrass 10

Soybean 2

Wild Proso 9

Table F COMPOUND

Rate (125 g/ha) 8

PREEMERGENCE

Barnyardgrass 9

Corn G4689A 6

Cotton 3

Crabgrass 9

Fall Panicum 9

Giant Foxtail 8

Green Foxtail 7

Signalgrass 8

Soybean 0

Wild Proso 9

Table F COMPOUND

Rate (62 g/ha) 8

PREEMERGENCE

Barnyardgrass 8

Corn G4689A 0

Cotton 2

Crabgrass 9

Fall Panicum 9

Giant Foxtail 8

Green Foxtail 6

Johnson Grass 8

Signalgrass 8

Soybean 0

Wild Proso 9

Table F COMPOUND

Rate (31 g/ha) 8

PREEMERGENCE

Barnyardgrass 8

Corn G4689A 0

Cotton 0

Crabgrass 8

Fall Panicum 7

Giant Foxtail 7

Green Foxtail 5

Johnson Grass 5

Signalgrass 7

Soybean 0

Wild Proso 9 Table F COMPOUND

Rate (16 g/ha) 8

PREEMERGENCE

Barnyardgrass 7

Com G4689A 0

Cotton 0

Crabgrass 8

Fall Panicum 5

Giant Foxtail 1

Green Foxtail 2

Johnson Grass 0

Signalgrass 4

Soybean 0

Wild Proso 8

TEST G

Seeds of bamyardgrass (Echinochloa crus-galli), cheatgrass (Bromus secalinup), cocklebur (Xanthium p ensylvan icum), crabgrass (Digitaria spp.), giant foxtail (Setaria faberii). morningglory (Ipomoea spp.), sorghum ( Sorgh um bicolor), velvetleaf (Abutilon theophrasti). and wild oat (Avena fatua) were planted into a sandy loam soil and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated postemergence with test chemicals. Plants ranged in height from two to eighteen cm and were in the two to three leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately eleven days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table G, are based on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test results.

Table G COMPOUND

Rate (2000 g/ha) 17

POSTEMERGENCE

Barnyardgrass 7

Cheatgrass 3

Cocklebur 2

Crabgrass 2

Giant foxtail 3

Morningglory 0

Sorghum 2

Velvetleaf 2

Wild oat 1

Rate (2000 g/ha) 17

PREEMERGENCE

Barnyardgrass 10

Cheatgrass 9

Cocklebur 0

Crabgrass 9

Giant foxtail 1

Morningglory 0

Sorghum 9

Velvetleaf 4

Wild oat 3

Table G COMPOUND

Rate (1000 g/ha) 18 19

POSTEMERGENCE

Barnyardgrass 1 0

Cheatgrass 0 0

Cocklebur 1 -

Crabgrass 1 0

Giant foxtail 1 0

Morningglory 0 0

Sorghum 1 0

Velvetleaf 0 1

Wild oat 1 0

Rate (1000 g/ha) 18 19

PREEMERGENCE

Barnyardgrass 2 8

Cheatgrass 0 5

Cocklebur 0 -

Crabgrass 0 3

Giant foxtail 3 0

Morningglory 0 0

Sorghum 0 6

Velvetleaf 0 3

Wild oat 0 1

Claims

What is claimed is: 1. Compounds of the formulas selected from the group consisting of I, II, III, IV and V:

and intermediates including stereoisomers thereof, wherein

X is OR⁵, SR⁵, C₁-C₆ acyloxy, benzoyloxy, halogen, N(R⁶)R⁷,

N(R⁶)OR⁷;

R¹ is H or straight chain C₁-C₃ alkyl optionally substituted with 1 or more deuteriums;

R² is H or C₁-C₄ alkyl; R³ is H, C₁-C₃ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₃ alkyl substituted with OCH₃ or OCH₂CH₃, or may be taken together with R² to form a 5 or 6-membered spiro or fused ring;

R⁴ is H, C₁-C₃ alkyl, C₂-C₄ alkenyl, C₁-C₆ acyl or benzoyl; R⁵ is H, C₁-C₃ alkyl optionally substituted with 1 or more deuteriums, hydroxyl, C₁-C₃ alkoxyls or halogens; C₂-C₄ alkenyl; C3-C4 alkynyl; or phenyl optionally substituted with 1-3 substituents selected from halogen, C₁-C₃ alkyl, C₁-C₃ alkoxyl, CN, C₁-C₃ haloalkyl, C₁-C₃ haloalkoxyl, C₁-C₃ alkylthio, C₂-C₄ alkenyl, C₁-C₄ alkynyl or NO₂;

R⁶ and R⁷ are independently H, C₁-C₃ alkyl or may be taken together to form a 5- or 6-membered saturated or unsaturated heterocyclic ring containing 1-4 nitrogens, 0-1 oxygen or 0-1 sulfur, each ring optionally substituted with 1-2 substituents selected from halogen, CH₃ or OCH₃;

Q is -CH₂W or

R⁸ is H, halogen, C₁-C₃ alkyl, OR⁹, SR⁹ or CN;

R⁹ is C₁-C₃ alkyl or C₁-C₃ haloalkyl;

J is CH₂, NR¹⁰ _, O, S or may be taken to form a double bond with an adjacent carbon;

R¹⁰ is H or C₁-C₃ alkyl;

q¹ is 0-2;

q² is 0-2; and W is phenyl optionally substituted with 1-3 substituents selected from halogen, C₁-C₃ alkyl, C₁-C₃ alkoxyl, OH,

CN, C₁-C₃ haloalkyl, C₁-C₃ haloalkoxyl, C₁-C₃ alkylthio,

C₂-C₄ alkenyl or C₂-C₄ alkynyl, or W is a 5-, 6- or

7-membered heterocycHc ring containing 0-2 nitrogens, 0-2 oxygens or 0-2 sulfurs, each ring optionally substituted with 1-2 substituents selected from halogen, CH₃ or OCH₃; provided that

1) the sum of ql and q² is 0-2 and

2) if the sum of q¹ ans q² is 0 then J is CH₂.

2. The compounds of Claim 1 wherein:

W is phenyl optionally substituted by 1-2 substituents

selected from halogen, CH₃ or OCH₃; or W is

tetrahydropyran, tetrahydrofuran, thiophene, thiazole, isoxazole, pyridine or pyrazine, each ring optionally substituted with 1-2 substituents selected from F, Cl, Br, CH₃ or OCH₃; and

Q is

3. The compounds of Claim 2 wherein:

R¹ is straight chain C₁-C₃ alkyl optionally substituted with 1 or more deuteriums;

R³ is H, C₁-C₃ alkyl or may be taken with R² to form a 5- or 6-membered spiro ring;

R⁴ is C₁-C₃ alkyl, C₁-C₆ acyl or benzoyl;

R⁸ is H, CH₃, halogen, OCH₃ or SCH₃.

4. The compounds of Claim 3 wherein:

X is OR⁵, SR⁵, C₁-C₆ acyloxy, benzoyloxy or N(R⁶)R⁷.

5. The compounds of Claim 4 wherein: R⁵ is H; C₁-C₃ alkyl optionally containing 1 or more deuteriums or C₁-C₃ alkoxyls; or phenyl optionally substituted with 1-2 substituents selected from halogen, CH₃ or OCH₃.

6. The compounds of Claim 5 wherein Q is

Q-1, Q-3, Q-6, Q-7 or Q-15.

7. The compounds of Claim 6 wherein the compound is a compound of Formula I.

8. The compounds of Claim 6 wherein the compound is a compound of Formula II.

9. The compounds of Claim 6 wherein the compound is a compound of Formula III.

10. The compounds of Claim 6 wherein thecompound is a compound of Formula IV.

11. The compounds of Claim 6 wherein the compound is a compound of Formula V.

12. The compound of Claim 11 which is:

5-(methoxy-d₃)-1-methyl-2-(phenylmethoxy)-9- oxabicyclo[3.3.1]nonane, exo-.

13. The compound of Claim 11 which is:

5-methoxy-1-methyl-2-(phenylmethoxy)-9-oxabicyclo- [3.3.1]nonane, exo-.

14. The compound of Claim 11 which is:

1-ethyl-5-methoxy-2-(phenylmethoxy)-9-oxabicyclo- [3.3.1]nonane, exo-.

15. The compound of Claim 11 which is:

2-[(2-fluorophenyl)methoxy]-5-methoxy-1-methyl-9- oxabicyclo[3.3.1]nonane, exo-.

16. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 1 and at least one of the following: surfactant, solid diluent or liquid diluent.

17. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compotmd of Claim 2 and at least one of the following: surfactant, solid diluent or liquid diluent.

18. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 3 and at least one of the following: surfactant, solid diluent or liquid diluent.

19. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 4 and at least one of the following: surfactant, solid diluent or liquid diluent.

20. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 5 and at least one of the following: surfactant, solid diluent or liquid diluent.

21. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 6 and at least one of the following: surfactant, solid diluent or liquid diluent.

22. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 7 and at least one of the following: surfactant, solid diluent or liquid diluent.

23. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 8 and at least one of the following: surfactant, sohd diluent or liquid diluent.

24. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 9 and at least one of the following: surfactant, sohd diluent or liquid diluent.

25. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 10 and at least one of the following: surfactant, sohd diluent or liquid diluent.

26. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 11 and at least one of the following: surfactant, solid diluent or liquid diluent.

27. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 12 and at least one of the following: surfactant, sohd diluent or liquid diluent.

28. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 13 and at least one of the following: surfactant, solid diluent or liquid diluent.

29. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim H and at least one of the following: surfactant, sohd diluent or liquid diluent.

30. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of the compound of Claim 15 and at least one of the following: surfactant, solid diluent or liquid diluent.

31. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 1.

32. A method for controlling the growth of undesired vegetation which comprises applying to the locus to-be protected an effective amount of a compound of Claim 2.

33. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 3.

34. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 4.

35. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 6.

36. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 7.

37. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 8.

38. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 9.

39. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 10.

40. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 11.

41. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 12.

42. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 13.

43. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 14.

44. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 15.

45. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 5.