# US 4,394,379 A · Amide phosphorothiolate derivatives and their use as pesticides

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- Number: US 4,394,379 A
- Document ID: US4394379A
- Status: Granted
- Kind: A
- Application number: 06/113,133
- Filed: 1980-01-17
- Granted: 1983-07-19
- Earliest claimed: 1978-07-21
- Assignees: Sumitomo Chemical Company, Limited
- Inventors: Osamu Kirino; Masachika Hirano; Hisami Takeda; Toshiro Kato
- Web page: https://patentgrep.com/patent/US4394379A

## CPC

- C07F 9/1651: {with hydroxyalkyl compounds with further substituents on alkyl}
- A01N 57/14: containing aromatic radicals
- A01N 57/30: containing aromatic radicals
- C07F 9/2408: {of hydroxyalkyl 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)
- 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

Amide phosphorothiolate derivatives of the formula, ##STR1## wherein X is an oxygen or sulfur atom, Y is an oxygen or sulfur atom or imino group, R.sub.1 and R.sub.2, which may be the same or different, are each a C.sub.1 -C.sub.3 alkyl group, R.sub.3 is a C.sub.1 -C.sub.4 alkyl group, R.sub.4 is a hydrogen atom or methyl group, R.sub.5 is a C.sub.1 -C.sub.3 alkyl, methoxy or ethoxy group, Z is a hydrogen atom, a methyl group or chlorine atom and n is 1 or 2, a process for producing said derivatives characterized by reacting the salt of thiophosphoric ester represented by the formula, ##STR2## wherein X, Y, R.sub.1 and R.sub.2 are as defined above and M is a sodium or potassium atom or ammonium group, with a haloacetamide derivative of the formula, ##STR3## wherein R.sub.3, R.sub.4, R.sub.5, Z and n are as defined above and W is a halogen atom, and a combined insecticide, acaricide, nematocide and/or fungicide containing said derivatives as an active ingredient.

## Claims

### Claim 1

A compound of the formula ##STR12## wherein X is an oxygen or sulfur atom, Y is an oxygen or sulfur atom or imino group, R.sub.1 and R.sub.2, which may be the same or different, are each a C.sub.1 -C.sub.3 alkyl group, R.sub.3 is a C.sub.1 -C.sub.4 alkyl group, R.sub.4 is a hydrogen atom or methyl group, R.sub.5 is a C.sub.1 -C.sub.3 alkyl, methoxy or ethoxy group, Z is a hydrogen atom, a methyl group or chlorine atom and n is 1 or 2.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein X is a sulfur atom, R.sub.1, R.sub.2 and R.sub.3, which may be the same or different, are each a C.sub.1 -C.sub.3 alkyl group, R.sub.4 is a hydrogen atom or methyl group, R.sub.5 is a C.sub.1 -C.sub.3 alkyl, methoxy or ethoxy group, Z is a methyl group or chlorine atom in the ortho-position on the phenyl ring, and n is 1.

### Claim 3 (depends on 1)

A compound according to claim 1, wherein X is a sulfur atom, R.sub.1, R.sub.2 and R.sub.3, which may be the same or different, are each a C.sub.1 -C.sub.3 alkyl group, R.sub.4 is a hydrogen atom or methyl group, R.sub.5 is a C.sub.1 -C.sub.3 alkyl, methoxy or ethoxy group, Z is a methyl group or chlorine atom, and n is 1 or 2, with the proviso that there is a Z group in the ortho-position on the phenyl ring.

### Claim 4 (depends on 1)

A compound according to claim 1, wherein X is a sulfur atom, Y is an oxygen atom, R.sub.1 and R.sub.2, which may be the same or different, are each a methyl or ethyl group, R.sub.3 is a methyl or ethyl group, R.sub.4 is a hydrogen atom or methyl group, R.sub.5 is a methyl, ethyl, methoxy or ethoxy group, Z is a hydrogen atom or a methyl group and n is 1 or 2.

### Claim 5 (depends on 1)

The compound according to claim 1, which is ##STR13##

### Claim 6 (depends on 1)

The compound according to claim 1, which is ##STR14##

### Claim 7 (depends on 1)

The comound according to claim 1, which is ##STR15##

### Claim 8 (depends on 1)

The compound according to claim 1, which is ##STR16##

### Claim 9 (depends on 1)

The compound according to claim 1, which is ##STR17##

### Claim 10 (depends on 1)

A method for controlling insects, mites, nematodes and/or fungi which comprises contacting the insects, mites, nematodes and/or fungi with an insecticidally, miticidally, nematocidally and/or fungicidally effective amount of at least one amide phosphorothiolate derivative as defined in claim 1.

### Claim 11 (depends on 1)

A method for controlling rice stem borers, houseflies and mites which comprises contacting the rice stem borers, houseflies and mites with an insecticidally and miticidally effective amount of at least one amide phosphorothiolate derivative as defined in claim 1.

### Claim 12 (depends on 1)

A method for controlling diseases caused by Phycomycetes which comprises contacting the Phycomycetes with a fungicidally effective amount of at least one amide phosphorothiolate derivative as defined in claim 1.

### Claim 13 (depends on 1)

An insecticidal, acaricidal, nematocidal and/or fungicidal composition comprising an inert carrier or diluent and at least one amide phosphorothiolate derivative as defined in claim 1 as an active ingredient in an insecticidally, acaricidally, nematocidally and/or fungicidally effective amount.