# US 4,400,197 A · N-(Optionally substituted 1,3-dioxolan- or dioxan-2-ylmethyl)-N-alkyl, alkenyl, or alkynyl-2,2-dichloroacetamides

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- Number: US 4,400,197 A
- Document ID: US4400197A
- Status: Granted
- Kind: A
- Application number: 06/276,309
- Filed: 1981-06-22
- Granted: 1983-08-23
- Earliest claimed: 1979-12-26
- Assignees: PPG Industries, Inc.
- Inventors: Jay K. Rinehart
- Web page: https://patentgrep.com/patent/US4400197A

## CPC

- C07D 319/06: not condensed with other rings
- A01N 25/32: Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
- C07D 317/28: Radicals substituted by nitrogen atoms (nitro radicals C07D317/16)
- 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

Disclosed are antidotal compounds for use with active thiocarbamate and/or chloroacetanilide herbicides to control weeds without affecting crops such as corn and soybeans. Compositions of the antidote and the active thiocarbamates and/or chloroacetanilides are also disclosed.

## Claims

### Claim 1

A composition containing:
(a) a herbicidally effective amount of N-dialkyl thiocarbamate; and
(b) an antidotally effective amount of a compound represented by the formula: ##STR10## wherein: R is ethyl, propyl, 1-methylethyl, 2-propenyl, butenyl, 2-methyl-2-propenyl, 2-propynyl or 1,1-dimethyl-2-propynyl;
R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently hydrogen or methyl; and
n is 0 or 1.

### Claim 2 (depends on 1)

The composition of claim 1 wherein N-dialkyl thiocarbamate herbicide is selected from S-ethyl dipropylthiocarbamate, S-ethyl diisobutylthiocarbamate, S-propyl dipropylthiocarbamate or S-ethyl diethylthiocarbamate.

### Claim 3 (depends on 1)

The composition of claim 1 wherein the weight ratio of N-dialkyl thiocarbamate herbicide to antidotal compound ranges from 18:1 to 6:1.

### Claim 4 (depends on 1)

The composition of claim 1 wherein the antidotal compound is N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)-2,2-dichloroacetamide.

### Claim 5

In a method of controlling weed growth among crops wherein a herbicidally effective amount of N-dialkyl thiocarbamate herbicide is used to control said weeds, the improvement residing in controlling said
weeds with said S-alkyl thiocarbamate herbicide in the presence of an antidotally effective amount of an antidotal compound represented by the formula: ##STR11## wherein: R is ethyl, propyl, 1-methylethyl, 2-propenyl, 2-butenyl, 2-methyl-2-propenyl, 2-propynyl or 1,1-dimethyl-2-propynyl;
R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently hydrogen or methyl; and
n is 0 or 1
to reduce the phytotoxic effect of the S-alkyl thiocarbamate on said crops.

### Claim 6 (depends on 5)

The improvement of claim 5 wherein the weight ratio of N-dialkyl thiocarbamate herbicide to antidotal compound ranges from 18:1 to 6:1.

### Claim 7 (depends on 5)

The improvement of claim 5 wherein the N-dialkyl thiocarbamate herbicide is selected from S-ethyl dipropylthiocarbamate, S-ethyl diisobutylthiocarbamate, S-propyl dipropylthiocarbamate or S-ethyl diethylthiocarbamate.

### Claim 8 (depends on 5)

The improvement of claim 5 wherein the antidotal compound is N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)-2,2-dichloroacetamide.

### Claim 9

A composition containing a herbicidally effective amount of S-ethyl diisopropyl thiocarbamate herbicide and an antidotally effective amount of N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)-2,2-dichloroacetamide.

### Claim 10

In a method of controlling weed growth in a corn crop wherein a herbicidally effective amount of S-ethyl diisopropyl thiocarbamate herbicide is used to control the weed growth, the improvement residing in controlling said weed growth with said S-ethyl diisopropyl thiocarbamate in the presence of an antidotally effective amount of N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)-2,2-dichloroacetamide to reduce the phytotoxic effect of the S-ethyl diisopropyl thiocarbamate on the corn.