# US 5,707,934 A · Plant growth regulation using 3-cyano-1-phenylpyrazoles such as fipronil

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- Number: US 5,707,934 A
- Document ID: US5707934A
- Status: Granted
- Kind: A
- Application number: 08/622,628
- Filed: 1996-03-27
- Granted: 1998-01-13
- Earliest claimed: 1995-04-28
- Assignees: Rhone-Poulenc Inc.
- Inventors: Reed Nathan Royalty; Nguyen Dang Long; Michael Thomas Pilato; Nicholas Mark Hamon; Ngadi Yahmad; Djoko Prabowo Sastrosatomo
- Web page: https://patentgrep.com/patent/US5707934A

## CPC

- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 47/02: the carbon atom having no bond to a nitrogen atom
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

This invention relates to a new method of plant growth regulation whereby a 1-phenylpyrazole such as fipronil is applied to a crop or a seed.

## Claims

### Claim 1

A method for treating plants in need of plant growth promotion which are not in need of insect control, said method comprising applying to said plants, to the seeds from which they grow or to the locus in which they grow, a non-phytotoxic, effective plant growth promoting amount of a compound having the formula: ##STR2## wherein: R.sub.1 is CN;
R.sub.2 is S(O).sub.n R.sub.3 ;
R.sub.3 is alkyl or haloalkyl;
R.sub.4 is --NR.sub.5 R.sub.6 ;
R.sub.5 and R.sub.6 are independently selected from the group consisting of hydrogen, alkyl, haloalkyl, C(O)alkyl and C(O)OR.sub.7 ;
R.sub.7 is alkyl;
X is C-R.sub.12 ;
R.sub.11 and R.sub.12 are independently halogen or hydrogen;
R.sub.13 is halogen, haloalkyl, haloalkoxy or SF.sub.5 ; and
n is 0, 1 or 2;
said plants, seeds and locus having substantially no insects present or expected in their vicinity during plant growth.

### Claim 2 (depends on 1)

A method according to claim 1, wherein the plant growth promoting amount of the compound of formula (I) applied is sufficient to provide at least one plant growth promoting effect selected from the group consisting of: (a) a more developed root system; (b) a tillering increase; (c) an increase in plant height; (d) a larger leaf blade; (e) fewer dead basal leaves; (f) stronger tillers; (g) a greener leaf color; (h) a need for less fertilizer; (i) a need for fewer seeds; (j) more productive tillers; (k) fewer nonproductive third tillers; (l) earlier flowering; (m) earlier grain maturity; (n) less plant verse; (o) longer panicles; (p) increased shoot growth; (q) improved plant vigor; (r) earlier germination; and (s) more fruit and better weight of fruit.

### Claim 3 (depends on 2)

A method according to claim 2, wherein the compound of formula (I) is 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethyl sulfinylpyrazole.

### Claim 4 (depends on 2)

A method according to claim 2, wherein said plants are selected from the group consisting of rice, corn, cereal, vegetable and soybean plants and turf.

### Claim 5 (depends on 4)

A method according to claim 4, wherein the compound of formula (I) is 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethyl sulfinylpyrazole.

### Claim 6 (depends on 1)

A method according to claim 1, wherein the plant growth promoting amount of the compound of formula (I) is sufficient to reduce the fertilizer requirements of said plants.

### Claim 7 (depends on 6)

A method according to claim 6, wherein the compound of formula (I) is 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethyl sulfinylpyrazole.

### Claim 8 (depends on 6)

A method according to claim 6, wherein said plants are selected from the group consisting of rice, corn, cereal, vegetable and soybean plants and turf.

### Claim 9 (depends on 8)

A method according to claim 8, wherein the compound of formula (I) is 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethyl sulfinylpyrazole.

### Claim 10 (depends on 1)

A method according to claim 1, wherein said plants are selected from the group consisting of rice, corn, cereal, vegetable and soybean plants and turf.

### Claim 11 (depends on 10)

A method according to claim 10, wherein the compound of formula (I) is 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl-4-trifluoromethyls ulfinylpyrazole.

### Claim 12 (depends on 1)

A method according to claim 1, wherein the compound of formula (I) is 5-amino-3-cyano-1 -(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole.

### Claim 13 (depends on 1)

A method according to claim 1, wherein the compound of formula (I) is applied to said plants or to the locus in which they grow in the form of granules at an application rate of from about 0.005 kg/ha to about 0.5 kg/ha of compound of formula (I).

### Claim 14 (depends on 13)

A method according to claim 13, wherein the application rate is from about 0.01 kg/ha to about 0.2 kg/ha of compound of formula (I).

### Claim 15 (depends on 1)

A method according to claim 1, wherein the compound of formula (I) is applied to said seeds at a dose rate of from about 2 to about 1000 grams per quintal of seed.

### Claim 16 (depends on 15)

A method according to claim 15, wherein the application rate is from about 5 to about 800 grams per quintal of seed.

### Claim 17 (depends on 16)

A method according to claim 16, wherein the application rate is from about 5 to about 250 grams per quintal of seed.

### Claim 18

A method for treating soybean plants in need of growth promotion, said method comprising applying to the seeds from which said soybean plants grow, prior to sowing said seeds, a non-phytotoxic, effective plant growth promoting amount of a compound having the formula: ##STR3## wherein: R.sub.1 is CN;
R.sub.2 is S(O).sub.n R.sub.3 ;
R.sub.3 is alkyl or haloalkyl;
R.sub.4 is --NR.sub.5 R.sub.6 ;
R.sub.5 and R.sub.6 are independently selected from the group consisting of hydrogen, alkyl, haloalkyl, C(O)alkyl and C(O)OR.sub.7 ;
R.sub.7 is alkyl;
X is C-R.sub.12 ;
R.sub.11 and R.sub.12 are independently halogen or hydrogen;
R.sub.13 is halogen, haloalkyl, haloalkoxy or SF.sub.5 ; and
n is 0, 1 or 2.

### Claim 19 (depends on 18)

A method according to claim 18, wherein the compound of formula (I) is 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethyl sulfinylpyrazole.

### Claim 20 (depends on 18)

A method according to claim 18, wherein the plant growth promoting amount of the compound of formula (I) applied is sufficient to provide at least one plant growth promoting effect selected from the group consisting of: (a) a more developed root system; (b) an increase in plant height; (c) a larger leaf blade; (d) a greener leaf color; (e) a need for less fertilizer; (f) a need for fewer seeds; (g) earlier flowering; (h) increased shoot growth; (i) improved plant vigor; (j) earlier germination; and (k) more fruit and better weight of fruit.

### Claim 21 (depends on 20)

A method according to claim 20, wherein the compound of formula (I) is 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethyl sulfinylpyrazole.

### Claim 22 (depends on 18)

A method accosting to claim 18, wherein the compound of formula (I) is applied to said seeds at a dose rate of from about 2 to about 1000 grams per quintal of seed.

### Claim 23 (depends on 22)

A method according to claim 22, wherein the application rate is from about 5 to about 800 grams per quintal of seed.

### Claim 24 (depends on 23)

A method according to claim 23, wherein the application rate is from about 5 to about 250 grams per quintal of seed.

### Claim 25

A method for treating soybean plants in need of growth promotion which are not in need of insect control, said method comprising applying to the seeds from which said soybean plants grow, prior to sowing said seeds, a non-phytotoxic, effective plant growth promoting amount of a compound having the formula: ##STR4## wherein: R.sub.1 is CN;
R.sub.2 is S(O).sub.n R.sub.3 ;
R.sub.3 is alkyl or haloalkyl;
R.sub.4 is --NR.sub.5 R.sub.6 ;
R.sub.5 and R.sub.6 are independently selected from the group consisting of hydrogen, alkyl, haloalkyl, C(O)alkyl and C(O)OR.sub.7 ;
R.sub.7 is alkyl;
X is C-R.sub.12 ;
R.sub.11 and R.sub.12 are independently halogen or hydrogen;
R.sub.13 is halogen, haloalkyl, haloalkoxy or SF.sub.5 ; and
n is 0, 1 or 2;
said plants and seeds having substantially no insects present or expected in their vicinity during plant growth.

### Claim 26 (depends on 25)

A method according to claim 25, wherein the compound of formula (I) is 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethyl sulfinylpyrazole.

### Claim 27 (depends on 25)

A method according to claim 25, wherein the plant growth promoting amount of the compound of formula (I) applied is sufficient to provide at least one plant growth promoting effect selected from the group consisting of: (a) a more developed root system; (b) an increase in plant height; (c) a larger leaf blade; (d) a greener leaf color; (e) a need for less fertilizer; (f) a need for fewer seeds; (g) earlier flowering; (h) increased shoot growth; (i) improved plant vigor; (j) earlier germination; and (k) more fruit and better weight of fruit.

### Claim 28 (depends on 27)

A method according to claim 27, wherein the compound of formula (I) is 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethyl sulfinylpyrazole.

### Claim 29 (depends on 25)

A method according to claim 25, wherein the compound of formula (I) is applied to said seeds at a dose rate of from about 2 to about 1000 grams per quintal of seed.

### Claim 30 (depends on 29)

A method according to claim 29, wherein the application rate is from about 5 to about 800 grams per quintal of seed.

### Claim 31 (depends on 30)

A method according to claim 30, wherein the application rate is from about 5 to about 250 grams per quintal of seed.