# US 2014/0155264 A1 · N-Thio-Anthranilamide Compounds and Their Use as Pesticides

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- Number: US 2014/0155264 A1
- Document ID: US20140155264A1
- Status: Published application
- Kind: A1
- Application number: 14/235,528
- Filed: 2012-08-10
- Published: 2014-06-05
- Earliest claimed: 2011-08-12
- Assignees: BASF SE
- Inventors: Florian Kaiser; Karsten Körber; Prashant Deshmukh; Deborah L. Culbertson; Paul Neese; Koshi Gunjima
- Web page: https://patentgrep.com/patent/US20140155264A1

## CPC

- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A61P 33/02: Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 409/14: containing three or more hetero rings
- 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
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to N-thio-anthranilamide compounds of the formula (I), the stereoisomers, the salts, the tautomers and the N-oxides thereof, wherein R1 is halogen or halomethyl; R2 is hydrogen, halogen or cyano; R3 is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C2-C6-alkenyl or the like; R4 is halogen; R5 and R6 independently of each other are optionally substituted C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl, or together represent an (hetero)aliphatic chain, or the like; k is 0 or 1. The present invention further relates to a method for combating or controlling invertebrate pests, to a method for protecting plant propagation material and/or the plants which grow therefrom, to plant propagation material comprising at least one compound according to the present invention, to a method for treating or protecting an animal from infestation or infection by parasites, to a process for the preparation of a composition for treating infested or infected animals and/or for protecting animals against infestation or infection by parasites, and to a compound according to the invention for use as a medicament.

## Claims

### Claim at position 1

1-26. (canceled)

### Claim 27

A compound of formula (I)
wherein
R1 is selected from the group consisting of halogen and halomethyl;
R2 is selected from the group consisting of hydrogen, halogen, halomethyl and cyano;
R3 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2-C6-haloalkinyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C(═O)Ra, C(═O)ORb and C(═O)NRcRd;
R4 is halogen;
R5, R6 are selected independently of one another from the group consisting of hydrogen, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, wherein the aforementioned aliphatic and cycloaliphatic radicals may be substituted with 1 to 10 substituents Re, and phenyl, which is unsubstituted or carries 1 to 5 substituents Rf; or
R5 and R6 together represent a C2-C7-alkylene, C2-C7-alkenylene or C6-C9-alkynylene chain forming together with the sulfur atom to which they are attached a 3-, 4-, 5-, 6-, 7-, 8-, 9 or 10-membered saturated, partially unsaturated or fully unsaturated ring, wherein 1 to 4 of the CH2 groups in the C2-C7-alkylene chain or 1 to 4 of any of the CH2 or CH groups in the C2-C7-alkenylene chain or 1 to 4 of any of the CH2 groups in the C6-C9-alkynylene chain may be replaced by 1 to 4 groups independently selected from the group consisting of C═O, C═S, O, S, N, NO, SO, SO2 and NH, and wherein the carbon and/or nitrogen atoms in the C2-C7-alkylene, C2-C7-alkenylene or C6-C9-alkynylene chain may be substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl; said substituents being identical or different from one another if more than one substituent is present;
Ra is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, and C1-C6-alkylsulfonyl, wherein one or more CH2 groups of the aforementioned radicals may be replaced by a C═O group, and/or the aliphatic and cycloaliphatic moieties of the aforementioned radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 substituents selected from the group consisting of C1-C4 alkoxy, phenyl, benzyl, pyridyl and phenoxy, wherein the last four radicals may be unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, (C1-C6-alkoxy)carbonyl, C1-C6-alkylamino and di-(C1-C6-alkyl)amino;
Rb is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, wherein one or more CH2 groups of the aforementioned radicals may be replaced by a C═O group, and/or the aliphatic and cycloaliphatic moieties of the aforementioned radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 substituents selected from C1-C4-alkoxy; phenyl, benzyl, pyridyl and phenoxy, wherein the last four radicals may be unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy and (C1-C6-alkoxy)carbonyl;
Rc, Rd are, independently from one another and independently of each occurrence, selected from the group consisting of hydrogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, wherein one or more CH2 groups of the aforementioned radicals may be replaced by a C═O group, and/or the aliphatic and cycloaliphatic moieties of the aforementioned radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from C1-C4-alkoxy;
C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, phenyl, benzyl, pyridyl and phenoxy, wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6 haloalkoxy and (C1-C6-alkoxy)carbonyl; or
Rc and Rd, together with the nitrogen atom to which they are bound, may form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or fully unsaturated heterocyclic ring which may additionally contain 1 or 2 further heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may optionally be substituted with halogen, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
Re is independently selected from the group consisting of halogen, cyano, nitro, —OH, —SH, —SCN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, wherein one or more CH2 groups of the aforementioned radicals may be replaced by a C═O group, and/or the aliphatic and cycloaliphatic moieties of the aforementioned radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from C1-C4-alkoxy;
C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, —ORa, —NRcRd, —S(O)nRa, —S(O)nNRcRd, —C(═O)Ra, —C(═O)NRcRd, —C(═O)ORb, —C(═S)Ra, —C(═S)NRcRd, —C(═S)ORb, —C(═S)SRb, —C(═NRc)Rb, —C(═NRc)NRcRd, phenyl, benzyl, pyridyl and phenoxy, wherein the last four radicals may be unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy; or
two vicinal radicals Re together form a group ═O, ═CH(C1-C4-alkyl), ═C(C1-C4-alkyl)C1-C4-alkyl, ═N(C1-C6-alkyl) or ═NO(C1-C6-alkyl);
Rf is independently selected from the group consisting of halogen, cyano, nitro, —OH, —SH, —SCN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, wherein one or more CH2 groups of the aforementioned radicals may be replaced by a C═O group, and/or the aliphatic and cycloaliphatic moieties of the aforementioned radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy;
C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylthio, —ORa, —NRcRd, —S(O)nRa, —S(O)nNRcRd, —C(═O)Ra, —C(═O)NRcRd, —C(═O)ORb, —C(═S)Ra, —C(═S)NRcRd, —C(═S)ORb, —C(═S)SRb, —C(═NRc)Rb, and —C(═NRc)NRcRd;
k is 0 or 1;
n is 0, 1 or 2;
or a stereoisomer, salt, tautomer or N-oxide thereof.

### Claim 28 (depends on 27)

The compound of claim 27, wherein R1 is selected from the group consisting of chlorine and bromine.

### Claim 29 (depends on 27)

The compound of claim 27, wherein R2 is selected from the group consisting of cyano, trifluoromethyl, chlorine and bromine.

### Claim 30 (depends on 27)

The compound of claim 27, wherein R3 is hydrogen.

### Claim 31 (depends on 27)

The compound of claim 27, wherein R4 is selected from the group consisting of chlorine and bromine.

### Claim 32 (depends on 27)

The compound of claim 27, wherein R5 and R6 are selected independently of one another from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the aforementioned radicals may be substituted with 1 to 10 substituents Re, and phenyl, which is unsubstituted or carries 1 to 4 radicals Rf, or R5 and R6 together represent a C3-C7-alkylene chain forming together with the sulfur atom to which they are attached a 4-, 5-, 6-, 7- or 8-membered saturated ring, wherein 1 or 2 of the CH2 groups in the C3-C7-alkylene chain may be replaced by 1 or 2 groups independently selected from the group consisting of C═O, C═S, O, S, N, NO, SO, SO2 and NH, and wherein the carbon and/or nitrogen atoms in the C3-C7-alkylene chain may be substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, C1-C2-alkyl, and C1-C2-haloalkyl, said substituents being identical or different from one another if more than one substituent is present.

### Claim 33 (depends on 27)

The compound of claim 27, wherein R5 and R6 are selected independently of one another from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the aforementioned radicals may be substituted with 1 to 4 substituents selected from the group consisting of halogen, cyano, C1-C6-alkyl and C3-C6-cycloalkyl; and phenyl, which is unsubstituted or carries 1, 2 or 3 radical selected from the group consisting of halogen, cyano, methyl, methoxy, trifluoromethyl and difluoromethyl, or R5 together with R6 form a bivalent moiety (CH2)m where m is from 3 to 7 and wherein one CH2 moiety may be replaced by S, SO or SO2.

### Claim 34 (depends on 27)

The compound of claim 27, wherein R5 and R6 are selected independently of one another from the group consisting of CH3, CH2CH3, CH═CH2, CH2CH2CH3, CH(CH3)2, CH2CH2CH2CH3, C(CH3)3, CH2CH(CH3)2, CH(CH3)CH2CH3, CH2CH2CH2CH2CH3, CH2CH2CH2CH2CH2CH3, CH2CH2CH(CH3)2, CH(CH3)CH(CH3)2, CH2CH2OH, CH2CH═CH2, CH2C≡CH, CH(CH3)CH═CH2, CHF2, CH2Cl, CH2CH2CN, CH2CH2Cl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl and phenyl,
or R5 together with R6 form a bivalent moiety selected from the group consisting of (CH2)4 and CH2SCH2CH2.

### Claim 35 (depends on 27)

The compound of claim 27, wherein k is 0.

### Claim 36 (depends on 27)

The compound of claim 27 having formula (I-a)

### Claim 37 (depends on 36)

The compound of claim 36, wherein R1, R2, R5 and R6 have one of the meanings given in any one of rows 1 to 58 of the following table:
row
R1
R2
R5
R6
1
Cl
Cl
CH3
CH3
2
Cl
CN
CH3
CH3
3
Br
Cl
CH3
CH3
4
Br
Br
CH3
CH3
5
CF3
Cl
CH3
CH3
6
CF3
Br
CH3
CH3
7
Cl
Cl
CH2CH2CH2CH2
8
Cl
CN
CH2CH2CH2CH2
9
Br
Cl
CH2CH2CH2CH2
10
Br
Br
CH2CH2CH2CH2
11
CF3
Cl
CH2CH2CH2CH2
12
CF3
Br
CH2CH2CH2CH2
13
Cl
Cl
C2H5
C2H5
14
Cl
Cl
CH(CH3)2
CH(CH3)2
15
Br
Cl
C2H5
C2H5
16
Br
Cl
CH(CH3)2
CH(CH3)2
17
Br
Br
C2H5
C2H5
18
Br
Br
CH(CH3)2
CH(CH3)2
19
CF3
Cl
C2H5
C2H5
20
CF3
Cl
CH(CH3)2
CH(CH3)2
21
CF3
Br
C2H5
C2H5
22
CF3
Br
CH(CH3)2
CH(CH3)2
23
Br
CF3
C2H5
C2H5
24
Br
CF3
CH(CH3)2
CH(CH3)2
25
Cl
CF3
C2H5
C2H5
26
Cl
CF3
CH(CH3)2
CH(CH3)2
27
Cl
CN
C2H5
C2H5
28
Cl
CN
CH(CH3)2
CH(CH3)2
29
Cl
Cl
CH2CH(CH3)2
CH2CH(CH3)2
30
Cl
CN
CH2CH(CH3)2
CH2CH(CH3)2
31
Br
Cl
CH2CH(CH3)2
CH2CH(CH3)2
32
Br
Br
CH2CH(CH3)2
CH2CH(CH3)2
33
CF3
Cl
CH2CH(CH3)2
CH2CH(CH3)2
34
CF3
Br
CH2CH(CH3)2
CH2CH(CH3)2
35
Cl
Cl
CH(CH3)2
C2H5
36
Cl
CN
CH(CH3)2
C2H5
37
Br
Cl
CH(CH3)2
C2H5
38
Br
Br
CH(CH3)2
C2H5
39
CF3
Cl
CH(CH3)2
C2H5
40
CF3
Br
CH(CH3)2
C2H5
41
Cl
Cl
cyclopropyl
C2H5
42
Cl
CN
cyclopropyl
C2H5
43
Br
Cl
cyclopropyl
C2H5
44
Br
Br
cyclopropyl
C2H5
45
CF3
Cl
cyclopropyl
C2H5
46
CF3
Br
cyclopropyl
C2H5
47
Cl
Cl
cyclopropyl
CH(CH3)2
48
Cl
CN
cyclopropyl
CH(CH3)2
49
Br
Cl
cyclopropyl
CH(CH3)2
50
Br
Br
cyclopropyl
CH(CH3)2
51
CF3
Cl
cyclopropyl
CH(CH3)2
52
CF3
Br
cyclopropyl
CH(CH3)2
53
Cl
Cl
—CH2—S—CH2—CH2—
54
Cl
CN
—CH2—S—CH2—CH2—
55
Br
Cl
—CH2—S—CH2—CH2—
56
Br
Br
—CH2—S—CH2—CH2—
57
CF3
Cl
—CH2—S—CH2—CH2—
58
CF3
Br
—CH2—S—CH2—CH2—

### Claim 38 (depends on 36)

The compound of claim 36, wherein R1, R2, R5 and R6 have one of the meanings given in any one of rows 1 to 27 of the following table:
row
R1
R2
R5
R6
1
Cl
Cl
CH2-cyclopropyl
CH2-cyclopropyl
2
Cl
Cl
CH2-cyclopropyl
C2H5
3
Cl
Cl
CH2CH2CH3
CH2CH2CH3
4
Cl
Br
CH(CH3)2
CH(CH3)2
5
Cl
Cl
CH2-cyclopropyl
i-Pr
6
Cl
Br
C2H5
C2H5
7
Cl
Cl
CH(CH3)2
CH(CH3)CH(CH3)2
8
Cl
Cl
CH(CH3)2
CH(CH3)—c-Pr
9
Cl
Cl
CH(CH3)CH(CH3)2
CH(CH3)CH(CH3)2
10
Cl
Cl
CH(CH3)CH(CH3)2
C2H5
11
Cl
CN
CH2-cyclopropyl
CH2-cyclopropyl
12
Cl
CN
CH2-cyclopropyl
C2H5
13
Cl
CN
CH2-cyclopropyl
CH(CH3)2
14
Cl
Cl
CH2(CH2)3CH3
CH2(CH2)3CH3
15
Cl
Cl
CH2CH2CH(CH3)2
CH2CH2CH(CH3)2
16
Cl
Cl
CH2-cyclobutyl
CH2-cyclobutyl
17
Cl
Cl
C2H5
CH2-cyclobutyl
18
Cl
Cl
CH2(CH2)4CH3
CH2(CH2)4CH3
19
Cl
Cl
CH2CH(C2H5)(CH2)3CH3
CH2CH(C2H5)(CH2)3CH3
20
Cl
Cl
CH2CH2OH
CH2CH2OH
21
Cl
Cl
CH2CH2-cyclopropyl
CH2CH2-cyclopropyl
22
Cl
Cl
CH2CH2-cyclopropyl
i-Pr
23
Cl
Cl
CH2CH2-cyclopropyl
C2H5
24
Cl
Cl
CH2-cyclobutyl
CH(CH3)2
25
Cl
Cl
CH2-cyclopentyl
CH2-cyclopentyl
26
Cl
Cl
CH2-cyclopentyl
C2H5
27
Cl
Cl
CH2-cyclopentyl
CH(CH3)2

### Claim 39 (depends on 27)

The compound of claim 27 which is 2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(diethyl-λ4-sulfanylidene)carbamoyl]phenyl]-5-(trifluoromethyl)pyrazole-3-carboxamide.

### Claim 40 (depends on 39)

A crystalline form of the compound of claim 39, which in an X-ray powder diffractogram at 25° C. and Cu-Kα radiation, shows at least four of the following reflexes, given as 2θ values: 8.07, 9.53, 11.00, 12.40, 14.31, 16.65, 18.97, 21.14, 21.48, 22.48.

### Claim 41 (depends on 27)

A pesticidal combination comprising at least one compound of claim 27 and at least one active compound selected from the group consisting of insecticides, acaricides, fungicides, herbicides, plant growth regulators, safeners and nematicides.

### Claim 42 (depends on 27)

An agricultural or veterinary composition comprising at least one compound of claim 27.

### Claim 43 (depends on 41)

An agricultural or veterinary composition comprising the pesticidal combination of claim 41.

### Claim 44 (depends on 27)

A method for combating or controlling invertebrate pests, comprising contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound of claim 27 except for a method performed on humans.

### Claim 45 (depends on 41)

A method for combating or controlling invertebrate pests, comprising contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of the pesticidal combination of claim 41, except for a method performed on humans.

### Claim 46 (depends on 42)

A method for combating or controlling invertebrate pests, comprising contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of the composition of claim 42, except for a method performed on humans.

### Claim 47 (depends on 27)

A method for protecting growing plants from attack or infestation by invertebrate pests, comprising contacting a plant, or soil or water in which the plant is growing or may grow, with a pesticidally effective amount of at least one compound of claim 27.

### Claim 48 (depends on 41)

A method for protecting growing plants from attack or infestation by invertebrate pests, comprising contacting a plant, or soil or water in which the plant is growing or may grow, with a pesticidally effective amount of the pesticidal compound of claim 41.

### Claim 49 (depends on 42)

A method for protecting growing plants from attack or infestation by invertebrate pests, comprising contacting a plant, or soil or water in which the plant is growing or may grow, with a pesticidally effective amount of the composition of claim 42.

### Claim 50 (depends on 27)

A method for the protection of seeds from soil insects and of the seedlings' roots and shoots from invertebrate pests comprising contacting the seeds before sowing and/or after pregermination with at least one compound of claim 27.

### Claim 51 (depends on 41)

A method for the protection of seeds from soil insects and of the seedlings' roots and shoots from invertebrate pests comprising contacting the seeds before sowing and/or after pregermination with the pesticidal combination of claim 41.

### Claim 52 (depends on 42)

A method for the protection of seeds from soil insects and of the seedlings' roots and shoots from invertebrate pests comprising contacting the seeds before sowing and/or after pregermination with the composition of claim 42.

### Claim 53 (depends on 27)

A seed trated with the compound of claim 27 in an amount of from 0.1 g to 10 kg per 100 kg of the plant propagation material.

### Claim 54 (depends on 41)

A seed treated with the pesticidal combination of claim 41 in an amount of from 0.1 g to 10 kg per 100 kg of the plant propagation material.

### Claim 55 (depends on 27)

A method for treating a non-human animal infested or infected by parasites or for preventing a non-human animal from getting infested or infected by parasites or for protecting a non-human animal against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the non-human animal a parasitically effective amount of the compound of claim 27.

### Claim 56 (depends on 41)

A method for treating a non-human animal infested or infected by parasites or for preventing a non-human animal from getting infested or infected by parasites or for protecting a non-human animal against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the non-human animal a parasitically effective amount of the pesticidal combination of claim 41.

### Claim 57 (depends on 42)

A method for treating a non-human animal infested or infected by parasites or for preventing a non-human animal from getting infested or infected by parasites or for protecting a non-human animal against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the non-human animal a parasitically effective amount of the composition of claim 42.