# US 8,785,630 B2 · Insecticidal triazines and pyrimidines

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- Number: US 8,785,630 B2
- Document ID: US8785630B2
- Status: Granted
- Kind: B2
- Application number: 13/760,925
- Filed: 2013-02-06
- Published: 2013-06-13
- Granted: 2014-07-22
- Earliest claimed: 2011-07-20
- Assignees: Vestaron Corporation
- Applicants: Vestaron Corporation
- Inventors: Robert M. Kennedy; Bruce A. Steinbaugh
- Web page: https://patentgrep.com/patent/US8785630B2

## CPC

- C07D 239/49: with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/68: with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N 43/84: six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
- C07D 239/48: Two nitrogen atoms
- C07D 251/48: Two nitrogen atoms
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- 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

## Abstract

The present invention describes novel triazines, their related pyrimidines and their use in controlling insects. This invention also includes new synthetic procedures, intermediates for preparing the compounds, pesticide compositions containing the compounds, and methods of controlling insects using the compounds.

## Claims

### Claim 1

A method of using a compound of Formula (I),
wherein:
Y is CR1;
R1 is —H, Halo or —C1-C4 alkyl;
Z is -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C6 alkylC6cycloalkyl, heterocyclic, —C1-C8 alkylheterocyclic,
X, is —H, —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl, heterocyclic, —C1-C8 alkylheterocyclic, —NRiRj or —C1-C8 alkylNRiRj;
R2 and R3 are independently —H or —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl, heterocyclic, —C1-C8 alkylheterocyclic, and —C1-C8 alkylNRiRj, but R2 and R3 are not both H;
Ri and Rj are independently —H, or —C1-C8 alkyl;
wherein heterocyclic is a 5-10 member cyclic or bicyclic aromatic or saturated —C1-C8 cycloaliphatic ring moiety containing 1, 2, or 3 heteroatoms selected from N, O, or S;
wherein aryl, —C3-C8 cycloalkyl and heterocyclic are optionally independently substituted with one to five substituents independently selected from -halo, —CN, —OH, —OCH2CH═CHCl, —C1-C6 alkyl, —O—C1-C6 alkyl, or —S—C1-C6 alkyl; and at each occurrence alkyl, is optionally substituted with 1-5 halo, —CN, or —OH in order to control and inhibit: insects, mites and nematodes, comprising applying an insect-inhibiting amount of a compound of Formula I to the locus, area to be protected or directly on the insects, mites and nematodes.

### Claim 2 (depends on 1)

A method of claim 1 wherein halo is Cl or F;
Ri and Rj are H or C1-C2 alkyl; and
R2 and R3 are independently —H or —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl, heterocyclic, —C1-C8 alkylheterocyclic, and —C1-C8 alkylNRiRj; but when one of R2 and R3 are -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl, heterocyclic, —C1-C8 alkylheterocyclic, and —C1-C8 alkylNRiRj then the other of either R2 or R3 is independently —H or —C1-C8 alkyl.

### Claim 3 (depends on 1)

A method of claim 1 wherein
X, Z, R2, and R3 are independently a —C1-C6 cycloalkyl, —C1-C6 alkylC6cycloalkyl, —C6 aryl, —C1-C6alkylC6 aryl or C6 heterocyclic or —C1-C6 alkylC6-heterocyclic or saturated or unsaturated optionally substituted ring, wherein
X, Z, R2, and R3 are optionally independently substituted with 1, 2 or 3, of —H, -halo, —CN, —OH, —OCH2CH═CHCl, —C1-C6 alkyl, —O—C1-C6 alkyl, or —S—C1-C6 alkyl;
wherein at each occurrence, any —C1-C6 alkyl, is optionally independently substituted with 1-5-halo, —CN or —OH.

### Claim 4 (depends on 3)

A method of claim 3 wherein
X, Z, and R2, and R3 are independently a heterocyclic or —C1-C6 alkylheterocyclic 6 member saturated or unsaturated optionally substituted ring, wherein
X, Z, and R2, or R3 is optionally independently substituted with 1 or 2 —H, -halo, —CN, —OH, —OCH2CH═CHCl, —C1-C6 alkyl, —O—C1-C6 alkyl, or —S—C1-C6 alkyl;
wherein at each occurrence, any —C1-C6 alkyl, is optionally independently substituted with 1-5-halo, —CN or —OH.

### Claim 5 (depends on 4)

A method of claim 4 wherein
X, Z, R2, and R3 are independently a heterocyclic or —C1-C6 alkylheterocyclic 6 member saturated or unsaturated optionally substituted ring, wherein
X, Z, and R2, or R3 is optionally independently substituted with 1 —H, -halo, —CN, —OH, —OCH2CH═CHCl, —C1-C6 alkyl, —O—C1-C6 alkyl, or —S—C1-C6 alkyl;
wherein at each occurrence, any —C1-C6 alkyl, is optionally independently substituted with 1-5-halo, —CN or —OH.

### Claim 6 (depends on 3)

A method of claim 3 wherein said heterocyclic or alkylheterocyclic is an aromatic unsaturated optionally substituted ring, a aliphatic saturated ring, or a combination of both unsaturated and saturated optionally substituted rings and the hetero atom is a non adjacent N or O or combination of N and O atoms.

### Claim 7 (depends on 3)

A method of claim 3 wherein
Z is -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, or —C1-C6 alkylC6cycloalkyl;
X is —H, —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl, —NRiRj or —C1-C8 alkylNRiRj;
when R2 is —H or —C1-C8 alkyl then R3 is —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl, and —C1-C8 alkylNRiRj; and
when R3 is —H or —C1-C8 alkyl then R2 is —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl, and —C1-C8 alkylNRiRj;
Ri and Rj are independently —H, or —C1-C8 alkyl.

### Claim 8 (depends on 7)

A method of claim 7 wherein
aryl is phenyl, alkylaryl is alkylphenyl and phenyl or alkylphenyl is optionally independently substituted with 1, 2 or 3-halo, —CN, —OH, —OCH2CH═CHCl, —C1-C6 alkyl, —O—C1-C6 alkyl, or —S—C1-C6 alkyl;
and at each occurrence alkyl, is optionally substituted with 1-5 halo, —CN, or —OH.

### Claim 9 (depends on 8)

A method of claim 8 wherein
X is optionally independently substituted with 1, 2 or 3-halo, —CN, —OH, —OCH2CH═CHCl, —C1-C6 alkyl, —O—C1-C6 alkyl, or —S—C1-C6 alkyl;
R2 or R3 is optionally independently substituted with 1 or 2-halo, —CN, —OH, —OCH2CH═CHCl, —C1-C6 alkyl, —O—C1-C6 alkyl, or —S—C1-C6 alkyl;
Z is optionally independently substituted with 1, 2 or 3-halo, —CN, —OH, —OCH2CH═CHCl, —C1-C6 alkyl, —O—C1-C6 alkyl, or —S—C1-C6 alkyl;
and at each occurrence alkyl, is optionally substituted with 1-5 halo, —CN, or —OH.

### Claim 10 (depends on 1)

A method of claim 1 wherein the aryl is phenyl and phenyl is optionally substituted with 1-3 R10, at any of the positions of any of the formula below; and
R10 is optionally independently substituted with one to five substituents independently selected from -halo, —CN, —OH, —OCH2CH═CHCl, —C1-C6 alkyl, —O—C1-C6 alkyl, or —S—C1-C6 alkyl; and at each occurrence alkyl, is optionally substituted with 1-5 halo, —CN, or —OH;

### Claim 11 (depends on 1)

A method of claim 1 wherein
X, Z, R2, and R3 are independently a heterocyclic or alkylheterocyclic 5, 6 or 10 member saturated or unsaturated optionally substituted ring,
optionally independently substituted with 1, 2 or 3, of —H, -halo, —CN, —OH, —OCH2CH═CHCl, —C1-C6 alkyl, —O—C1-C6 alkyl, or —S—C1-C6 alkyl;
wherein at each occurrence, any —C1-C6 alkyl, is optionally independently substituted with 1-5-halo, —CN or —OH.

### Claim 12 (depends on 11)

A method of claim 11 wherein
Z is -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, or —C1-C6alkylC6cycloalkyl;
X is heterocyclic or —C1-C8 alkylheterocyclic;
when R2 is —H or —C1-C8 alkyl, then R3 is —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl and —C1-C8 alkylNRiRj;
when R3 is —H or —C1-C8 alkyl, then R2 is —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl and —C1-C8 alkylNRiRj.

### Claim 13 (depends on 11)

A method of claim 11 wherein
Z is heterocyclic or —C1-C8 alkylheterocyclic,
X is —H, —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl, —NRiRj or —C1-C8 alkylNRiRj;
when R2 is —H or —C1-C8 alkyl, then R3 is —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl and —C1-C8 alkylNRiRj; and
when R3 is —H or —C1-C8 alkyl, then R2 is —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl and —C1-C8 alkylNRiRj.

### Claim 14 (depends on 11)

A method of claim 11 wherein
Z is -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, or —C1-C6alkylC6cycloalkyl;
X is —H, —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl, —NRiRj or —C1-C8 alkylNRiRj;
R2 is —H or —C1-C8 alkyl, when R3 is heterocyclic and —C1-C8 alkylheterocyclic;
R3 is —H or —C1-C8 alkyl, when R2 is -heterocyclic and —C1-C8 alkylheterocyclic.

### Claim 15 (depends on 1)

A method of claim 1 wherein Formula I is selected from Formulas II-CR1, III-CR1, and IV-CR1,

### Claim 16 (depends on 15)

A method of claim 15 wherein R1 is —H, —F or —CF3.

### Claim 17 (depends on 1)

A method of claim 1 wherein the compounds are selected from

### Claim 18 (depends on 1)

A method of claim 1 wherein
X, Z, R2, and R3 are independently a —C1-C6 cycloalkyl, —C1-C6 alkylC6cycloalkyl, C6 aryl, —C1-C6alkylC6 aryl or C6 heterocyclic or —C1-C6 alkylC6-heterocyclic or saturated or unsaturated optionally substituted ring, wherein
X, Z, and either R2, or R3 is optionally independently substituted with 1, 2 or 3, of —H, -halo, —CN, —OH, —OCH2CH═CHCl, —C1-C6 alkyl, —O—C1-C6 alkyl, or —S—C1-C6 alkyl;
wherein at each occurrence, any —C1-C6 alkyl, is optionally independently substituted with 1-5-halo, —CN or —OH.

### Claim 19 (depends on 1)

The method of claim 1 using a compound selected from:
N-(4-chlorophenyl)-2-phenyl-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)pyrimidin-4-amine;
6-(2-chloro-6-fluorophenyl)-N-(4-chlorophenyl)-2-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)pyrimidin-4-amine;
N-((6-chloropyridin-3-yl)methyl)-6-phenyl-2-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)pyrimidin-4-amine;
N-(4-chlorophenyl)-6-phenyl-2-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)pyrimidin-4-amine; N-(4-chlorophenyl)-4-phenyl-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)pyrimidin-2-amine;
6-(2-chloro-6-fluorophenyl)-N-(6-chloropyridin-3-yl)-2-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)pyrimidin-4-amine; and
N-(4-chlorobenzyl)-6-phenyl-2-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)pyrimidin-4-amine.

### Claim 20

An insecticidal composition, with an optional phytologically-acceptable carrier comprising the compounds of Formula I, useful for the control of insects, mites and nematodes, where Formula I is:
wherein:
Y is N;
R1 is —H, Halo or —C1-C4 alkyl;
Z is -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C6 alkylC6cycloalkyl, heterocyclic, —C1-C8 alkylheterocyclic,
X, is —H, —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl, heterocyclic, —C1-C8 alkylheterocyclic, —NRiRj or —C1-C8 alkylNRiRj;
R2 and R3 are independently —H or —C1-C8 alkyl, -aryl, —C1-C8 alkylaryl, —C3-C8 cycloalkyl, —C1-C8 alkylC3-C8 cycloalkyl, heterocyclic, —C1-C8 alkylheterocyclic, and —C1-C8 alkylNRiRj, but R2 and R3 are not both H;
Ri and Rj are independently —H, or —C1-C8 alkyl;
wherein heterocyclic is a 5-10 member cyclic or bicyclic aromatic or saturated —C1-C8 cycloaliphatic ring moiety containing 1, 2, or 3 heteroatoms selected from N, O, or S;
wherein aryl, —C3-C8 cycloalkyl and heterocyclic are optionally independently substituted with one to five substituents independently selected from -halo, —CN, —OH, —OCH2CH═CHCl, —C1-C6 alkyl, —O—C1-C6 alkyl, or —S—C1-C6 alkyl; and
at each occurrence, alkyl is optionally substituted with 1-5 halo, —CN, or —OH.

### Claim 21 (depends on 20)

The composition of claim 20 applied in the form of a spray, topical treatment, gel, seed coating, microcapsulation, bait, ear tag, bolus, fogger, aerosol or dust to the locus of an insect.

### Claim 22 (depends on 20)

The composition of claim 20 where the insecticidal composition is in the form of water soluble, water-suspendable or emulsifiable formulation a wettable dry powder or a liquid in the form of an emulsifiable concentrate or aqueous suspension.

### Claim 23 (depends on 20)

The composition of claim 20 wherein the concentration of the active compound is from about 10% to about 90% by weight.

### Claim 24 (depends on 20)

An insecticidal composition of claim 20 wherein Formula I is combined with one or more insecticides fungicides or herbicides in order to control undesired pests.