Method to inhibit ethylene responses in plants

1. A method of inhibiting an ethylene response in a plant comprising the step of contacting the plant with an effective ethylene response-inhibiting amount of a cyclopropene derivative of formula I or II:

or a mixture thereof, wherein:

a) each R 2 , R 3 , and R 4 is independently a group of the formula:

-(L) n -Z

wherein:

i) n is an integer from 0 to 12 and p is an integer from 3 to 10;

ii) each L is independently selected from a member of group D, E, or J wherein:

D is of the formula:

E is of the formula:

J is of the formula:

wherein:

A) each X and Y is independently a group of the formula:

-(L) m -Z;

and

B) m is an integer from 0 to 8; and

C) no more than two E groups are adjacent to each other and no J groups are adjacent to each other;

iii) each Z is independently selected from:

A) hydrogen, halo, cyano, nitro, nitroso, azido, chlorate, bromate, iodate, isocyanato, isocyanido, isothiocyanato, pentafluorothio, or

B) a group G, wherein G is an unsubstituted or substituted; unsaturated, partially saturated, or saturated; monocyclic, bicyclic, tricyclic, or fused; carbocyclic or heterocyclic ring system wherein;

1) when the ring system contains a 3 or 4 membered heterocyclic ring, the heterocyclic ring contains 1 heteroatom;

2) when the ring system contains a 5, or more membered heterocyclic ring or a polycyclic heterocyclic ring, the heterocyclic or polycyclic heterocyclic ring contains from 1 to 4 heteroatoms;

3) each heteroatom is independently selected from N, O, and S;

4) the number of substituents is from 0 to 5 and each substituent is independently selected from X

b) the total number of non-hydrogen atoms in each compound is 50 or less;

its enantiomers, stereoisomers, salts, and mixtures thereof; or a composition thereof.

2. A method of inhibiting an ethylene response in a plant, comprising contacting the plant with an effective ethylene response-inhibiting amount of a compound of formula III:

wherein:

a) each R 1 and R 2 is independently a group of the formula:

-(L) n -Z

wherein:

i) n is an integer from 0 to 12 and q is an integer from 2 to 11;

ii) each L is independently selected from a member of group D, E, or J wherein:

D is of the formula:

E is of the formula:

J is of the formula:

wherein:

A) each X and Y is independently a group of the formula:

-(L) m -Z;

and

B) m is an integer from 0 to 8; and

C) no more than two E groups are adjacent to each other and no J groups are adjacent to each other; and

iii) each Z is independently selected from:

A) hydrogen, halo, cyano, nitro, nitroso, azido, chlorate, bromate, iodate, isocyanato, isocyanido, isothiocyanato, pentafluorothio, or

B) a group G, wherein G is an unsubstituted or substituted; unsaturated, partially saturated, or saturated; monocyclic, bicyclic, tricyclic, or fused; carbocyclic or heterocyclic ring system wherein;

1) when the ring system contains a 3 or 4 membered heterocyclic ring, the heterocyclic ring contains 1 heteroatom;

2) when the ring system contains a 5, or more membered heterocyclic ring or a polycyclic heterocyclic ring, the heterocyclic or polycyclic heterocyclic ring contains from 1 to 4 heteroatoms;

3) each heteroatom is independently selected from N, O, and S;

4) the number of substituents is from 0 to 5 and each substituent is independently selected from X

b) the total number of non-hydrogen atoms in each compound is 50 or less;

its enantiomers, stereoisomers, salts, and mixtures thereof; or a composition thereof.

3. The method of claim 1 or claim 2 , wherein the ethylene response is one or more of ripening or senescence of flowers, fruits, and vegetables; abscission of foliage, flowers, and fruit; the shortening of life of ornamental plants, cut flowers, shrubbery, seeds, or dormant seedlings; inhibition of growth; stimulation of growth; auxin activity; inhibition of terminal growth; control of apical dominance; increase in branching; increase in tillering; changing the morphology of plants, modifying the susceptibility to plant pathogens such as fungi; changing bio-chemical compositions; inducing pest resistance; abortion or inhibition of flowering or seed development; lodging effects; stimulation of seed germination; breaking of dormancy; hormone effects; and epinasty effects.

4. The method of claim 1 , wherein the compound is of formula I and one of R 3 and R 4 is hydrogen.

5. The method of claim 1 , wherein the compound is of formula II and one of R 2 and R 3 is hydrogen.

6. The method of claim 2 , wherein one of R 1 and R 2 is hydrogen.

7. The method of claim 1 or claim 2 , wherein n is from 0 to 8.

8. The method of claim 1 or claim 2 , wherein m is from 0 to 4.

9. The method of claim 1 , wherein p is from 4 to 7.

10. The method of claim 2 , wherein q is from 4 to 6.

11. The method of claim 1 or claim 2 , wherein:

a) each D is independently —CXY—, —SiXY—, —CO—, or —CS—;

b) each E is independently —O—, —S—, —NX—, or —SO 2 —;

c) each X and Y is independently H, halo, OH, SH, —C(O)(C 1 –C 4 )alkyl-, —C(O)O(C 1 –C 4 )alkyl-, —O—(C 1 –C 4 )alkyl, —S—(C 1 –C 4 )alkyl, or substituted or unsubstituted (C 1 –C 4 )alkyl; and

d) each Z is independently H, halo, or G.

12. The method of claim 1 or claim 2 , wherein R 2 , R 3 , and R 4 , when present, are each independently selected from hydrogen and (C 1 –C 4 )alkyl.