# US 5,708,032 A · Fluoroalkenyl compounds and their use as pest control agents

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- Number: US 5,708,032 A
- Document ID: US5708032A
- Status: Granted
- Kind: A
- Application number: 08/447,460
- Filed: 1995-05-23
- Granted: 1998-01-13
- Earliest claimed: 1994-10-26
- Assignees: Monsanto Company
- Inventors: Dennis Paul Phillion; Peter Gerrard Ruminski; Gopichand Yalamanchili
- Web page: https://patentgrep.com/patent/US5708032A

## CPC

- C07D 239/545: with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- A01N 35/04: containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
- A01N 37/22: the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- A01N 37/28: containing the group [IMAGE cpc-sch-A01N-0937.gif]; Thio analogues thereof
- A01N 37/46: N-acyl derivatives
- A01N 41/04: Sulfonic acids; Derivatives thereof
- A01N 41/06: Sulfonic acid amides
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 47/02: the carbon atom having no bond to a nitrogen atom
- A01N 47/34: containing the groups [IMAGE cpc-sch-A01N-0947.gif], e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
- A01N 55/00: Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00)
- A01N 57/20: containing acyclic or cycloaliphatic radicals
- C07C 45/004: {by reaction with organometalhalides}
- C07C 49/80: containing halogen
- C07C 53/21: containing fluorine
- C07C 53/50: of acids containing three or more carbon atoms
- C07C 57/52: containing halogen
- C07C 233/09: with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
- C07C 255/29: containing cyano groups and acylated amino groups bound to the carbon skeleton
- C07C 259/06: having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C 281/06: Compounds containing any of the groups [IMAGE cpc-sch-C07C-0973.gif], e.g. semicarbazides
- C07C 309/15: the nitrogen atom of at least one of the amino groups being part of any of the groups [IMAGE cpc-sch-C07C-0975.gif], X being a hetero atom, Y being any atom
- C07C 309/51: at least one of the nitrogen atoms being part of any of the groups [IMAGE cpc-sch-C07C-0976.gif], X being a hetero atom, Y being any atom
- C07C 311/51: Y being a hydrogen or a carbon atom
- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 233/56: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D 239/38: One sulfur atom
- C07D 239/52: Two oxygen atoms
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07F 7/081: {comprising at least one atom selected from the elements N, O, halogen, S, Se or Te}
- C07F 9/302: {Acyclic unsaturated acids}
- C07F 9/3808: {Acyclic saturated acids which can have further substituents on alkyl}
- C07F 9/3826: {Acyclic unsaturated acids}
- C07F 9/4015: {Esters of acyclic unsaturated acids}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops, these compounds having the structure: ##STR1## where Q is --(C.dbd.S)--R.sub.1 and R.sub.1 is --OR.sub.5, --SR.sub.5, halogen, --NHOH or --NR.sub.5 R.sub.6. Each of R.sub.5 and R.sub.6 is independently hydrogen; an aliphatic or an aromatic group; a C.sub.1 -C.sub.12 aliphatic amine group; a C.sub.2 -C.sub.12 aliphatic carboxylic acid group; or R.sub.5 and R.sub.6 when taken together with the N of R.sub.1 are a protein amino acid or a cyclic group. Polar compounds are particularly useful for systemic control of pests.

## Claims

### Claim 1

A compound having the structure ##STR28## wherein Q is C(.dbd.S)R.sub.1 wherein R.sub.1 is NHOH or NR.sub.6 R.sub.7 ;
R.sub.6 and R.sub.7 are each independently
(i) an aliphatic or an aromatic group, optionally substituted with at least one group selected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl;
(ii) a C.sub.1 -C.sub.12 aliphatic amine group, optionally substituted with at least one group selected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl;
(iii) a C.sub.2 -C.sub.12 aliphatic carboxylic acid group, optionally substituted with at least one group selected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl;
with the proviso that when one of R.sub.6 or R.sub.7 is an aliphatic carboxylic acid group, optionally substituted with at least one group selected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl;
the other R group can not be an aliphatic group, an aromatic group or a second aliphatic carboxylic acid group; or
any agronomically acceptable salt thereof.

### Claim 2 (depends on 1)

A compound of claim 1 wherein R.sub.1 is --NHOH--R.sub.6 R.sub.7.

### Claim 3 (depends on 1)

A composition for controlling nematode infestation of a plant comprising an effective amount of a compound of claim 1 in an agronomically acceptable carrier.

### Claim 4

A method of systemically controlling nematode, insect or acarid infestation of a plant, comprising applying to a plant locus an effective amount of a compound having the structure: ##STR29## wherein Q is C(.dbd.S)R.sub.1 wherein R.sub.1 is NHOH or NR.sub.6 R.sub.7 ; and
R.sub.6 and R.sub.7 are each independently
(i) an aliphatic or an aromatic group, optionally substituted with at least one group selected from hydroxy, alkoxy; halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl;
(ii) a C.sub.1 -C.sub.12 aliphatic amine group, optionally substituted with at least one group selected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl;
(iii) a C.sub.2 -C.sub.12 aliphatic carboxylic acid group, optionally substituted with at least one group selected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl;
with the proviso that when one of R.sub.6 or R.sub.7 is an aliphatic carboxylic acid group, optionally substituted with at least one group selected from hydroxy, alkoxy, halo, nitro, amino, thiol, alkylthio, carboxyl, alkoxycarbonyl, and phenyl;
the other R group can not be an aliphatic group, an aromatic group or a second aliphatic carboxylic acid group; or
any agronomically acceptable salt thereof.