IP Library › Granted Patent US 8,022,089

Granted Patent B2

US 8,022,089 · App. 12/509,859 · Granted Sep 20, 2011

Isoxazoline-substituted benzamide compound and pesticide

Assignee: Nissan Chemical Industries, Ltd.

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Quick Facts

Patent No.: US 8,022,089
App. No.: 12/509,859
Granted: Sep 20, 2011
Kind: B2

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Abstract

An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof: wherein A 1 , A 2 and A 3 independently of one another are carbon atom or nitrogen atom, G is benzene ring, etc., X is halogen atom, C 1 -C 6 haloalkyl, etc., Y is halogen atm, C 1 -C 6 alkyl, etc., R 1 is C 1 -C 12 alkyl arbitrarily substituted with R 16 , C 3 -C 12 alkenyl, arbitrarily substituted with R 16 is oxygen atom or sulfur atom, —N(R 20 )R 19 , etc., R 2 is hydrogen atom, C 1 -C 4 alkoxy C 1 -C 6 alkyl, etc., R 3 is C 1 -C 6 haloalkyl, etc., R 16 is halogen atom, cyano, phenyl substituted with (Z) p1 , D-1 to D-60, E-1 to E-49, etc., R 19 is phenyl, phenyl substituted with (Z) p1 , etc., R 20 is hydrogen atom, C 1 -C 6 alkyl, etc., Z is halogen atom, nitro, C 1 -C 4 alkoxy, etc., D-1 to D-60 are 5- or 6-membered aromatic heterocyclic rings, E-1 to E-49 are 5- or 6-membered saturated heterocyclic rings, m is an integer of 0 to 5, n is an integer of 0 to 4, p1 is an integer of 1 to 5. The pesticide containing these compounds.

Claims (777)

1. A method for controlling endo- or ecto-parasites of mammals or birds, the endo- or ecto-parasite being selected from the group consisting of Rust Red Flour Beetle, Musca domestica , German Cockroach, Broad Mite, Spide Mite, Ctenocephalides felis and American Dog Tick, the method comprising administering to a mammal or bird an effective amount of an endo- or ecto-parasiticide comprising, as an active ingredient, one or more compounds selected from the group consisting of:

(X) m

(Y) n

R 2

R 1

3,5-Cl 2

2-CH 3

CH(CH 3 )CH 2 OCH 3

3,5-Cl 2

2-CH 3

N(CH 3 )(D-47d)CF 3

3,5-Cl 2

2-CH 3

D-47a

(X) m

R 3

R 1

3,5-Cl 2

CF 3

E-4a

(X) m

R 3

(Y) n

R 1

3-Br

CF 3

2-CH 3

CH 2 CF 3

3-Br

CF 3

2-CH 3

CH 2 (D-47a)

3-I

CF 3

2-CH 3

CH 2 (D-47a)

4-I

CF 3

2-CH 3

CH 2 (D-47a)

3-CF 3

CF 3

2-CH 3

CH 2 CF 3

3-OCF 3

CF 3

2-CH 3

CH 2 CF 3

3-OCF 3

CF 3

2-CH 3

CH 2 (D-47a)

3-SCF 3

CF 3

2-CH 3

CH 2 (D-47a)

3,5-F 2

CF 3

2-CH 3

CH 2 (D-47a)

3,5-Cl 2

CHF 2

2-CH 3

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-Br

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-I

CH 2 C(O)NHCH 2 CH 2 Cl

3,5-Cl 2

CF 3

2-CH 3

c-Bu

3,5-Cl 2

CF 3

2-CH 3

CH 2 Bu-c

3,5-Cl 2

CF 3

2-CH 3

CH 2 CF 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 CH 2 OCH 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 CH 2 OEt

3,5-Cl 2

CF 3

2-CH 3

CH 2 (E-4a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (E-10a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 CH 2 SEt

3,5-Cl 2

CF 3

2-CH 3

CH 2 CH(CH 3 )S(O)CH 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 CH(CH 3 )SO 2 CH 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 C(O)CH 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 C(CH 3 )═NOCH 3

3,5-Cl 2

CF 3

2-CH 3

CH(Ph)CN

3,5-Cl 2

CF 3

2-CH 3

CH 2 C(O)OCH 3

3,5-Cl 2

CF 3

2-CH 3

CH(CH 3 )C(O)OCH 3 (D)

3,5-Cl 2

CF 3

2-CH 3

CH 2 C(O)NHCH 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 C(O)N(CH 3 ) 2

3,5-Cl 2

CF 3

2-CH 3

CH 2 C(O)NHEt

3,5-Cl 2

CF 3

2-CH 3

CH 2 C(O)NHPr-i

3,5-Cl 2

CF 3

2-CH 3

CH 2 C(O)NHCH 2 CH 2 Cl

3,5-Cl 2

CF 3

2-CH 3

CH 2 C(O)NHCH 2 CF 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 C(O)NHCH 2 CH═CH 2

3,5-Cl 2

CF 3

2-CH 3

CH 2 C(O)N(CH 3 )CH 2 CH═CH 2

3,5-Cl 2

CF 3

2-CH 3

CH 2 C(O)NHCH 2 C≡CH

3,5-Cl 2

CF 3

2-CH 3

CH(CH 3 )C(O)NHCH 2 CH 2 Cl

3,5-Cl 2

CF 3

2-CH 3

CH 2 CH═CH 2

3,5-Cl 2

CF 3

2-CH 3

CH 2 CH═CCl 2

3,5-Cl 2

CF 3

2-CH 3

CH 2 Ph

3,5-Cl 2

CF 3

2-CH 3

CH(CH 3 )Ph

3,5-Cl 2

CF 3

2-CH 3

CH(Et)Ph

3,5-Cl 2

CF 3

2-CH 3

C(CH 3 ) 2 Ph

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-1a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-3a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-10b)Cl

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-17a)CH 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-17b)Cl

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-21b)CF 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-22a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-23b)Cl

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-31a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-34a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-35a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-38a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

CH(CH 3 )(D-47a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-47c)Cl

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-47e)Cl

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-48a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-48e)Cl

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-50a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-51a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-53b)CH 3

3,5-Cl 2

CF 3

2-CH 3

NHC(O)OEt

3,5-Cl 2

CF 3

2-CH 3

N(CH 3 )Ph

3,5-Cl 2

CF 3

2-CH 3

NH(D-47b)Cl

3,5-Cl 2

CF 3

2-CH 3

NH(D-50a)

3,5-Cl 2

CF 3

2-CH 3

N(CH 3 )(D-50a)

3,5-Cl 2

CF 3

2-CH 3

D-48a

3,5-Cl 2

CF 3

2-CH 3

D-50a

3,5-Cl 2

CF 3

2-CH 3

D-51a

3,5-Cl 2

CF 3

2-Et

CH 2 CF 3

3,5-Cl 2

CF 3

2-Et

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-OCF 3

CH 2 CF 3

3,5-Cl 2

CF 3

2-OCF 3

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-SCH 3

CH 2 (D-47a)

3,5-Cl 2

CF 2 Cl

2-Cl

CH 2 (D-47a)

3,5-Cl 2

CF 2 Cl

2-CH 3

CH 2 CH 2 OEt

3,5-Cl 2

CF 2 Cl

2-CH 3

CH 2 (D-22a)

3,5-Cl 2

CF 2 Cl

2-CH 3

CH 2 (D-47a)

3,5-Cl 2

CF 2 CF 3

2-CH 3

CH 2 (D-47a)

3,5-Br 2

CF 3

2-C1

CH 2 (D-22a)

3,5-Br 2

CF 3

2-C1

CH 2 (D-47a)

3,5-Br 2

CF 3

2-CH 3

CH 2 CF 3

3,5-Br 2

CF 3

2-CH 3

CH 2 CH 2 OCH 3

3,5-Br 2

CF 3

2-CH 3

CH 2 C(O)NHCH 2 CH 2 Cl

3,5-Br 2

CF 3

2-CH 3

CH 2 C(O)NHCH 2 CF 3

3,5-Br 2

CF 3

2-CH 3

CH 2 (D-22a)

3,5-Br 2

CF 3

2-CH 3

CH 2 (D-47a)

3,5-(CF 3 ) 2

CF 3

2-CH 3

CH 2 CF 3

3,5-(CF 3 ) 2

CF 3

2-CH 3

CH 2 (D-47a)

3-CF 3 -5-OCH 3

CF 3

2-CH 3

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 CH 2 CF 3

3,5-Cl 2

CF 3

2-CH 3

CH(CF 3 )OCH 3

3,5-Cl 2

CF 3

2-CH 3

(E-9b)CH 2 CF 3

3,5-Cl 2

CF 3

2-CH 3

CH(CH 3 )C(O)NHCH 2 CF 3

3,5-Cl 2

CF 3

2-CH 3

CH(CH 3 )(D-1a)

3,5-Cl 2

CF 3

2-CH 3

CH(CH 3 )(D-21a)

3,5-Cl 2

CF 3

2-CH

CH(CF 3 )(D-38a)

3,5-Cl 2

CF 3

2-CH 3

C(O)NHCH 2 CF 3

3,5-Cl 2

CF 3

2-CH 3

C(S)NHCH 2 CF 3

3,5-Cl 2

CF 3

2-CH 3

NHC(O)NHCH 2 CH 2 C1

3,5-Cl 2

CF 3

2-CH 3

(D-15a)CH 3

3 4-Cl 2

CF 3

2-CH 3

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-I

CH 2 C(O)NHCH 2 CF 3

3,5-Cl 2

CF 3

2-I

(D-47d)Cl

3,5-Cl 2

CF 3

2-I

(D-50c)Cl

3,5-Cl 2

CF 3

2-CH 3

CH 2 OCH 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 OEt

3,5-Cl 2

CF 3

2-CH 3

CH 2 OPr-n

3,5-Cl 2

CF 3

2-CH 3

CH 2 OPr-i

3,5-Cl 2

CF 3

2-CH 3

CH 2 OCH 2 CH 2 Cl

3,5-Cl 2

CF 3

2-CH 3

CH 2 OCH 2 CHF 2

3,5-Cl 2

CF 3

2-CH 3

CH 2 OCH 2 CF 3

3,5-Cl 2

CF 3

2-CH 3

CH(CH 3 )OH

3,5-Cl 2

CF 3

2-CH 3

E-4a

3,5-Cl 2

CF 3

2-CH 3

E-5a(R)

3,5-Cl 2

CF 3

2-CH 3

E-23a

3,5-Cl 2

CF 3

2-CH 3

CH 2 SCH 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 S(O)CH 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 SO 2 CH 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 SC(O)CH 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-22b)SCH 3

3,5-Cl 2

CF 3

2-CH 3

C(O)NHCH 2 CH═CH 2

3,5-Cl 2

CF 3

2-CH 3

C(O)NHCH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

3,5-Cl 2

CF 3

2-CH 3

Ph-3-F

3,5-Cl 2

CF 3

2-CH 3

Ph-4-F

3,5-Cl 2

CF 3

2-CH 3

Ph-4-Cl

3,5-Cl 2

CF 3

2-CH 3

Ph-4-OCF 3

3,5-Cl 2

CF 3

2-CH 3

Ph-3-CN

3,5-Cl 2

CF 3

2-CH 3

Ph-3,4-F 2

3,5-Cl 2

CF 3

2-CH 3

Ph-3,5-Cl 2

3,5-Cl 2

CF 3

2-CH 3

(D-47d)Cl

3,5-Cl 2

CF 3

2-CH 3

(D-50c)Cl

3,5-Cl 2

CF 2 Cl

2-CH 3

CH 2 C(O)NHCH 2 CF 3

3,5-Cl 2 -4-CH 3

CF 3

2-CH 3

CH 2 (D-47a)

3,5-Cl 2 -4-N(CH 3 ) 2

CF 3

2-CH 3

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

(E-23b)OCH 3

(X) m

R 3

(Y) n

R 2

R 1

3,5-Cl 2

CF 3

2-CH 3

CH 3

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 CF 3

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 C≡CH

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

C(O)CH 3

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

C(O)Et

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

C(O)OCH 3

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

C(O)OBu-i

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

C(O)OCH 2 CH 2 Cl

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

C(O)OCH 2 CH 2 OCH 3

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

C(O)OCH 2 CH═CH 2

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-48e)Cl

3,5-Cl 2

CF 3

2-CH 3

c-Pr

CH 2 (D-49a)

3,5-Cl 2

CF 3

2-CH 3

C(O)CH 3

N(CH 3 )Ph

3,5-Cl 2

CF 3

2-CH 3

C(O)OCH 3

N(CH 3 )Ph

3,5-Cl 2

CF 2 Cl

2-CH 3

C(O)CH 3

CH 2 CF 3

3,5-Cl 2

CF 3

2-CH 3

CH 2 OEt

3,5-Cl 2

CF 3

2-CH 3

CH 3

CH 2 OCH 2 CF 3

3,5-Cl 2

CF 3

2-CH 3

C(O)CH 3

CH 2 OCH 2 CF 3

3,5-Cl 2

CF 3

2-CH 3

CH 3

E-4a

3,5-Cl 2

CF 3

2-CH 3

CH 2 OCH 3

E-4a

(X) m

R 3

(Y) n

R 2

R 1

3,5-Cl 2

CF 3

—

CH 2 CF 3

3,5-Cl 2

CF 3

—

CH 2 (D-47a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-22a)

3,5-Cl 2

CF 3

2-CH 3

CH 2 (D-47a)

and

(X) m

R 3

(Y) n

3,5-Cl2

CF3

2-CH3

C(O)OCH 2(D-47a)

wherein

2. The method of claim 1 wherein said administration is oral administration.

3. The method of claim 1 wherein said administration is parenteral administration.

4. The method of claim 1 wherein said administration is injection.

5. The method of claim 1 wherein said administration is intramuscular, subcutaneous, intravenous or intraperitoneal injection.

6. The method of claim 1 wherein said administration is transdermal administration.

7. The method of claim 1 wherein said administration is transnasal administration.

8. The method of claim 1 wherein said administration is dipping, spray, bathing, washing, pouring-on, spotting-on or dusting.

9. A method for controlling endo- or ecto-parasites of mammals or birds, the endo- or ecto-parasite being selected from the group consisting of Rust Red Flour Beetle, Musca domestica , German Cockroach, Broad Mite, Spide Mite, Ctenocephalides felis and American Dog Tick, the method comprising administering to a mammal or bird an effective amount of an endo- or ecto-parasiticide comprising as an active ingredient, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl)benzamide, an optically active form, or a salt thereof.

10. The method of claim 9 wherein said administration is oral administration.

11. The method of claim 9 wherein said administration is parenteral administration.

12. The method of claim 9 wherein said administration is injection.

13. The method of claim 9 wherein said administration is intramuscular, subcutaneous, intravenous or intraperitoneal injection.

14. The method of claim 9 wherein said administration is transdermal administration.

15. The method of claim 9 wherein said administration is transnasal administration.

16. The method of claim 9 wherein said administration is dipping, spray, bathing, washing, pouring-on, spotting-on or dusting.

17. A method for controlling endo- or ecto-parasites of mammals or birds, the endo- or ecto-parasite being selected from the group consisting of Rust Red Flour Beetle, Musca domestica , German Cockroach, Broad Mite, Spide Mite, Ctenocephalides felis and American Dog Tick, the method comprising administering to a mammal or bird an effective amount of an endo- or ecto-parasiticide comprising, as an active ingredient, one or more compounds selected from the group consisting of:

wherein

(X) m is 3,5-Cl 2 ;

Y is 2-CH 3 ;

R 1 is CH(CH 3 )CH2OCH 3 , N(CH 3 )(D-47d)CF 3 , or D-47a; and

R 2 is H;

wherein

(X) m is 3,5-Cl 2 ;

R 1 is E-4a; and

R 3 is CF 3 ;

wherein

(X) m is 3-Br, 3-I, 4-I, 3-CF 3 , 3-OCF 3 , 3-SCF 3 , 3,5-F 2 , 3,5-Br 2 , 3,5-(CF 3 ) 2 , 3-CF 3 -5-OCH 3 , 3,5-Cl 2 , 3,4-Cl 2 , or 3,5-Cl 2 -4-CH 3 , or 3,5-Cl 2 -4-N(CH 3 ) 2 ;

Y is 2-CH 3 , 2-Br, 2-Et, 2-SCH 3 , 2-Cl, 2-I, or 2-OCF 3 ;

R 1 is CH 2 CF 3 , CH 2 (D-47a), c-Bu, CH 2 Bu-c, CH 2 CH 2 OCH 3 , CH 2 CH 2 OEt, CH 2 (E-4a), CH 2 (E-10a), CH 2 CH 2 OEt, CH 2 CH(CH 2 )S(O)CH 3 , CH 2 CH(CH 3 )SO 2 CH 3 , CH 2 C(O)CH 3 , CH 2 C(CH 3 )═NOCH 3 , CH(Ph)CN, CH(CH 3 )C(O)OCH 3 (D), CH 2 C(O)NHCH 3 , CH 2 C(O)N(CH 3 ) 2 , CH 2 C(O)NHEt, CH 2 C(O)NHPr-i, CH 2 C(O)NHCH 2 CH 2 Cl, CH 2 C(O)NHCH 2 CF 3 , CH 2 C(O)NHCH 2 CH═CH 2 , CH 2 C(O)N(CH 3 )CH 2 CH═CH 2 , CH 2 C(O)NHCH 2 C≡CH, CH(CH 3 )C(O)NHCH 2 CH 2 Cl, CH 2 CH═CH 2 , CH 2 CH═CCl 2 , CH 2 Ph, CH(CH 3 )Ph, C(CH 3 ) 2 Ph, CH 2 (D-1a), CH 2 (D-3a), CH 2 (D-10b)Cl, CH 2 (D-17a)CH 3 , CH 2 (D-17b)Cl, CH 2 (D-21b)CF 3 , CH 2 (D-22a), CH 2 (D-23b)Cl, CH 2 (D-31a), CH 2 (D-34a), CH 2 (D-35a), CH(CH 3 )(D-47a), CH 2 (D-47c)Cl, CH 2 (D-47e)Cl, CH 2 (D-48a), CH 2 (D-48e)Cl, CH 2 (D-50a), CH 2 (D-51a), CH 2 (D-53b)CH 3 , NHC(O)OEt, N(CH 3 )Ph, NH(D-47b)Cl, NH(D-50a), N(CH 3 )(D-50a), D-51a, CH(CF 3 )OCH 3 , (E-9b)CH 2 CF 3 , CH(CH 3 )C(O)NHCH 2 CF 3 , CH(CH 3 )(D-21a), CH(CF 3 )(D-38a), C(O)NHCH 2 CF 3 , C(S)NHCH 2 CF 3 , (D-15a)CH 3 , CH 2 (D-47a), CH 2 C(O)NHCH 2 CF 3 , (D-50c)Cl, CH 2 OCH 3 , CH 2 OEt, CH 2 OPr-n, CH 2 OPr-i, CH 2 OCH 2 CH 2 Cl, CH 2 OCH 2 CHF 2 , CH 2 OCH 2 CF 3 , CH(CH 3 )OH, E-4a, E-5a(R), E-23a, CH 2 SCH 3 , CH 2 S(O)CH 3 , CH 2 SO 2 CH 3 , C(O)NHCH 2 CH═CH 2 , Ph-3-F, (D-47d)Cl, (E-23b)OCH 3 , CH 2 C(O)NHCH 2 CH 2 Cl, CH 2 C(O)OCH 3 , CH(Et)Ph, CH 2 (D-38a), D-48a, D-50a, CH(CH 3 )(D-1a), NHC(O)NHCH 2 CH 2 Cl, CH 2 SC(O)CH 3 , CH 2 (D-22b)SCH 3 , C(O)NHCH 2 (D-47a), Ph, Ph-4-F, Ph-4-Cl, Ph-4-OCF 3 , Ph-3-CN, Ph-3,4-F 2 , Ph-3,5-Cl 2 , or (D-50c)Cl; and

R 3 is CHF 2 , CF 2 Cl, CF 2 CF 3 , or CF 3 ;

wherein

(X) m is 3,5-Cl 2 ;

Y is 2-CH 3 ;

R 1 is CH 2 (D-47a), CH 2 (D-48e)Cl, CH 2 (D-49a), N(CH 3 )Ph, CH 2 CF 3 , CH 2 OEt, CH 2 OCH 2 CF 3 , or E-4a;

R 2 is CH 3 , CH 2 CF 3 , CH 2 C≡CH, C(O)CH 3 , C(O)Et, C(O)OCH 3 , C(O)OBu-i, C(O)OCH 2 CH 2 Cl, C(O)OCH 2 CH 2 OCH 3 , C(O)OCH 2 CH═CH 2 , Et, c-Pr, CH 2 OEt, or CH 2 OCH 3 ; and

R 3 is CF 3 or CF 2 Cl;

wherein

(X) m is 3,5-Cl 2 ;

Y is 2-CH 3 ;

R 1 is CH 2 CF 3 , CH 2 (D-47a), CH 2 (D-22a), or CH 2 (D-47a);

R 2 is H; and

R 3 is CF 3 ; and

wherein

(X) m is 3,5-Cl 2 ;

Y is 2-CH 3 ;

R is C(O)OCH 2 (D-47a); and

R 3 is CF 3 ;

wherein

Et is ethyl, c-Bu and Bu-c is cyclic butyl, Bu-I is iso-butyl, ph is phenyl, Pr-I is isopropyl, Pr-n is N-propyl, and c-Pr is cyclic-propyl.

Assignments (2)

CHANGE OF NAME Recorded Sep 21, 2018

From: NISSAN CHEMICAL INDUSTRIES, LTD.

To: NISSAN CHEMICAL CORPORATION

Reel/Frame 047128/0788 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 14, 2017

From: TAKII, SHINJI

To: NISSAN CHEMICAL INDUSTRIES, LTD.

Reel/Frame 042710/0163 →

Priority Claims (2)

JP 2004-061749 · Mar 5, 2004 · national

JP 2004-200119 · Jul 7, 2004 · national

Continuity (3)

Division 11514921 · Sep 5, 2006

Continuation In Part PCTJP2005004268 · Mar 4, 2005

Related Publication 20090312330A1 · Dec 17, 2009