# US 11,998,008 B2 · Pesticides and methods of controlling pests

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- Number: US 11,998,008 B2
- Document ID: US11998008B2
- Status: Granted
- Kind: B2
- Application number: 16/763,034
- Filed: 2018-11-15
- Published: 2021-04-01
- Granted: 2024-06-04
- Earliest claimed: 2017-11-16
- Assignees: The State of Israel, Ministry of Agriculture & Rural Development, Agricultural Research Organization (ARO) (Volcani Center)
- Applicants: The State of Israel, Ministry of Agriculture & Rural Development, Agricultural Research Organization (ARO) (VOLCANI CENTER)
- Inventors: David Ezra; Orna Liarzi; Ariel Ewenson
- Web page: https://patentgrep.com/patent/US11998008B2

## CPC

- A01N 35/06: containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
- A01N 25/30: characterised by the surfactants
- A01N 31/02: Acyclic compounds
- A01N 35/02: containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
- 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 37/02: Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
- 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

Disclosed herein are agricultural biocontrol compounds and compositions comprising the compounds, and methods of using the same. Specifically, nematacide fungicidal and herbecidial compounds, compositions comprising thereof, and methods for preventing and inhibiting nematodes, fungi and weed growth are disclosed herein.

## Claims

### Claim 1

A method of killing a fungus or reducing growth thereof, comprising exposing a soil infested with the fungus to a non-phytotoxic fungicide effective amount of a composition comprising trans-2-octenal as the sole fungicide; wherein the non-phytotoxic fungicide effective amount is a concentration of trans-2-octenal of 1-300 ppm within said soil.

### Claim 2 (depends on 1)

The method of claim 1, wherein the composition further comprises water.

### Claim 3 (depends on 1)

The method of claim 1, further comprising a deodorizing compound.

### Claim 4 (depends on 3)

The method of claim 3, wherein said compound and said deodorizing compound are at a ratio of at least 1:1.5 by weight.

### Claim 5 (depends on 3)

The method of claim 3, comprising 40-70% by weight of said deodorizing compound.

### Claim 6 (depends on 2)

The method of claim 2, further comprising a glycol ether solvent and one or more surfactant selected from an anionic surfactant, a nonionic surfactant, or a combination thereof, and wherein a weight ratio between said compound and said one or more surfactant is between 10:1 and 1:1.

### Claim 7 (depends on 1)

The method of claim 1, wherein the soil pathogen is selected from the group consisting of: Meloidogyne javanica, Aspergillus niger, Botrytis cinerea, Alternaria alternata, Sclerotium rolfsii, Rhizoctonia solani, Fusarium oxysporum f sp. Radicis-cucumerinum, Lasiodiplodia theobromas, Neoscytalidium dimidiatum, Talaromyces spp., Phoma tracheiphila, Colletotrichum spp., Verticillium spp., Pythium spp., Fusarium oxysporum f sp. radicis-lycopersici (Forl) and Penicillium digitatum including any combination thereof.

### Claim 8 (depends on 5)

The method of claim 5, wherein said aliphatic diol is selected from the group consisting of: 4-oxa-2,6-heptandiol, 2-(2-hydroxy-propoxy)-propan-1-ol, and 2-(2-hydroxy-1-methyl-ethoxy)-propan-1-ol.

### Claim 9 (depends on 6)

The method of claim 6, comprising 5-15% by weight of said glycol ether.

### Claim 10 (depends on 6)

The method of claim 6, wherein any one of: (i) said anionic surfactant is a linear alkylbenzene sulfonate; and (ii) said nonionic surfactant is an ethoxylated castor oil.

### Claim 11 (depends on 10)

The method of claim 10, comprising (i) 2-10% by weight of said anionic surfactant, or (ii) 5-15% by weight of ethoxylated castor oil, or (iii) a combination thereof.

### Claim 12

A method of killing a soil pathogen or reducing growth thereof, comprising exposing a soil infested with the soil pathogen to a composition comprising a pesticide effective amount of trans-2-octenal as the sole pesticide; wherein said exposing is at a non-phytotoxic amount of trans-2-octenal ranging between 1 and 300 ppm within said soil; and wherein the pesticide effective amount is a concentration of 0.5-2500 ppm in said composition.

### Claim 13 (depends on 12)

The method of claim 12, wherein the compound is represented by Formula IV:
wherein the dashed bond represents at least one double bond between two adjacent carbons at positions 1 to 4, and R3 represents one to four substituents being independently at each occurrence selected from the group consisting of: hydrogen, halo, hydroxy, alkoxy, aryloxy, cycloalkyloxy, heterocyclyloxy, heteroaryloxy, formyl, —S(═O)Ra, —S(═O)2Ra, —C(═O)Ra, —C(═O)ORa, wherein Ra is independently at each occurrence alkyl, alkenyl, alkynyl, cycloalkyl, aryl, alkylaryl, heterocyclyl or heteroaryl; amino, alkylamino, dialkylamino, arylamino, diarylamino, alkylarylamino, cycloalkylamino, heterocyclylamino, heteroarylamino, amido, alkylamido, dialkylamido, arylamido, diarylamido, alkylarylamido, cycloalkylamido, heterocyclylamido, heteroarylamido, cyano, nitro, carboxyl, carboxyalkyl, carboxyaryl, or acyl.

### Claim 14 (depends on 12)

The method of claim 12, wherein the compound is represented by Formula IV (a):

### Claim 15 (depends on 12)

The method of claim 12, wherein the compound is represented by Formula V:
wherein the dashed bond represents at least one double bond between two adjacent carbons at position 1 to 5, and R3 represents one to five substituents being independently at each occurrence selected from the group consisting of: H, halo, heterocyclyl, heteroaryl, hydroxy, alkoxy, aryloxy, cycloalkyloxy, heterocyclyloxy, heteroaryloxy, formyl, —S(═O)Ra, —S(═O)2Ra, —C(═O)Ra, —C(═O)ORa, wherein Ra is independently at each occurrence alkyl, alkenyl, alkynyl, cycloalkyl, aryl, alkylaryl, heterocyclyl or heteroaryl; amino, alkylamino, dialkylamino, arylamino, diarylamino, alkylarylamino, cycloalkylamino, heterocyclylamino, heteroarylamino, amido, alkylamido, dialkylamido, arylamido, diarylamido, alkylarylamido, cycloalkylamido, heterocyclylamido, heteroarylamido, cyano, nitro, carboxyl, carboxyalkyl, carboxyaryl, or acyl.

### Claim 16 (depends on 15)

The method of claim 15, wherein the compound is represented by Formula V(a):

### Claim 17 (depends on 12)

The method of claim 12, wherein said pestis a soil pathogen selected from the group consisting of: nematodes, fungi, microorganisms and weed, or any combination thereof.

### Claim 18 (depends on 12)

The method of claim 12, wherein said soil pathogen is a fungus.