DESCRIPTION OF THE PRIOR ART 
German Offen. No. 2,033,908 of Pyne et al [Chem. Abs. 76 99501t(1972)] and 
German Offen. No. 2,039,215 of D'Amico et al [Chem. Abs. 74-99859z (1971)] 
disclose herbicidal pyrrolidinyl carboxanilides and thiocarboxanilides. 
U.S. Pat. No. 3,639,608 of Pyne et al discloses fungicidal pyrrolidinyl 
carboxanilides and thiocarboxanilides. 
DESCRIPTION OF THE INVENTION 
The herbicidal compounds of the invention are represented by the formula 
##STR2## 
wherein X is hydrogen, fluoro, chloro, bromo, iodo, trifluoromethyl, 
trichloromethyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon 
atoms or cyano and n is 1, 2 or 3. When n is 2 or 3, the substituents 
represented by X may be the same or different. 
Preferred compounds of the invention are those wherein X is hydrogen, 
fluoro, chloro, trifluoromethyl or alkyl of 1 to 4 carbons and n is 1 to 
2. Most preferred compounds of the invention are those wherein X is fluoro 
or chloro. 
The compounds of formula I can exist as the levo or dextro enantiomers or 
as mixtures thereof, and the present invention relates to any or all of 
these forms. 
Representative compounds of the invention include: 
1-(2-hydroxymethylpyrrolidinyl)carboxanilide, 
1-(2-hydroxymethylpyrrolidinyl)-p-bromocarboxanilide 
1-(2-hydroxymethylpyrrolidinyl)-o-trichloromethylcarboxanilide 
1-(2-hydroxymethylpyrrolidinyl)-m-cyanocarboxanilide, 
1-(2-hydroxymethylpyrrolidinyl)-p-methoxycarboxanilide, 
1-(2-hydroxymethylpyrrolidinyl)-o-iodo-p-methylcarboxanilide, 
1-(2-hydroxymethylpyrrolidinyl)-o-chloro-p-bromocarboxanilide. 
The compounds of the invention are prepared by reacting 
2-hydroxymethylpyrrolidine and a phenyl isocyanate represented by the 
formula 
##STR3## 
wherein X and n are as previously defined. Generally, the reaction is 
conducted by reacting substantially equimolar amounts of the pyrrolidine 
and the isocyanate in an inert organic diluent at a temperature of about 
0.degree. C to 100.degree. C. The reaction is generally complete within 1 
to 24 hours. The carboxanilide product is recovered and purified by 
conventional procedures such as extraction, crystallization and 
chromatography.

EXAMPLE 1 
Preparation of 1-(2-hydroxymethylpyrrolidinyl)-o-fluorocarboxanilide 
A solution of 4.1 (0.03 mol) o-fluorophenyl isocyanate in 10 ml 
dimethoxyethane was added dropwise to a solution of 3 g (0.1 mol) 
2-hydroxymethylpyrrolidine (levo-enantiomer) in 50 ml dimethoxymethane. 
The resulting reaction mixture was stirred for about 16 hours at 
25.degree. C. Evaporation of the dimethoxyethane under reduced pressure 
gave an oil which solidified on standing. The solid was stirred in ethyl 
ether, filtered and dried to give 4.9g product, as a white solid, m.p. 
127.5.degree.-129.degree. C. 
The compounds tabulated in Table I were prepared by a procedure similar to 
that described above. The structure of the compounds were vertified by 
quantitative elemental analysis, and by infrared spectroscopy and/or 
nuclear magnetic resonance analysis. Compounds Nos. 1-11 are the 
levo-enantiomers (prepared from levo-(2-hydroxymethylpyrrolidine)) and the 
compounds Nos. 12-14 are a racemic mixture of d,l-enantiomers (prepared 
from d,l-(2-hydroxymethylpyrrolidine)). 
EXAMPLE 2 
Herbicidal Tests 
The compounds of the present invention are, in general, herbicidal in both 
pre- and post-emergent applications. For pre-emergent control of 
undesirable vegetation, the herbicidal compounds will be applied in 
herbicidally effective amounts to the locus or growth medium of the 
vegetation, e.g., soil infested with seeds and/or seedlings of such 
vegetation. Such application will inhibit the growth of or kill the seeds, 
germinating seeds and seedlings. For post-emergent applications, the 
herbicidal compounds will be applied directly to the foliage and other 
plant parts. Generally, the herbicidal compounds of the invention are 
effective against weed grasses as well as broadleaved weeds. Some may be 
selective with respect to the type of application and/or type of weed. 
The compounds of the present invention can be used alone as herbicides. 
However, it is generally desirable to apply the compounds in herbicidal 
compositions comprising one or more of the herbicidal compounds intimately 
admixed with a biologically inert carrier. The carrier may be a liquid 
diluent or a solid, e.g., in the form of dust powder or granules. In the 
herbicidal composition, the active herbicidal compounds can be from about 
0.01 to 95% by weight of the entire composition. 
Suitable liquid diluent carriers include water and organic solvents, e.g., 
hydrocarbons such as benzene, toluene, kerosene, diesel oil, fuel oil, and 
petroleum naphtha. Suitable solid carriers are natural clays such as 
kaolinite, atalpulgite, and montmorillonite. In addition, talcs, 
pyrophillite, diatomaceous silica, synthetic fine silicas, calcium 
aluminosilicate and tricalcium phosphate are suitable carriers. Organic 
materials such as walnut-shell flour, cottonseed hulls, wheat flour, wood 
flour or redwood-bark flour may also be used as solid carriers. 
The herbicidal composition will also usually contain a minor amount of a 
surface-active agent. Such surface agents are those commonly known as 
wetting agents, dispersing agents and emulsifying agents, and can be 
anionic, cationic or nonionic in character. The herbicidal compositions 
may also contain other pesticides, adjuvants, stabilizers, conditioners, 
fillers, and the like. 
The amount of herbicidal compound or composition administered will vary 
with the particular plant part or plant growth medium which is to be 
contacted, the general location of application -- i.e., sheltered areas 
such as greenhouses, as compared to exposed areas such as fields -- as 
well as the desired type of control. Generally for both pre- and 
post-emergent control, the herbicidal compounds of the invention are 
applied at rates of 0.2 to 60 kg/ha, and the preferred rate is in the 
range 0.5 to 40 kg/ha. 
Pre- and post-emergent herbicidal tests on representative compounds of the 
invention were made using the following methods: 
Pre-Emergent Test 
An acetone solution of the test compound was prepared by mixing 750 mg of 
the compound, 220 mg of a nonionic surfactant and 25 ml of acetone. This 
solution was added to approximately 125 ml of water containing 156 mg of 
surfactant. 
Seeds of the test vegetation were planted in a pot of soil and the test 
solution was sprayed uniformly onto the soil surface at a dose of 33 
microgram/cm.sup.2. The pot was watered and placed in a greenhouse. The 
pot was watered intermittently and was observed for seedling emergence, 
health of emerging seedlings, etc., for a 3-week period. At the end of 
this period, the herbicidal effectiveness of the compound was rated based 
on the physiological observations. A 0-to-100 scale was used, 0 
representing no phytotoxicity, 100 representing complete kill. The results 
of these tests appear in Table II. 
Post-Emergent Test 
The test compound was formulated in the same manner as described above for 
the pre-emergent test. The concentration of the test compound in this 
formulation was 5000 ppm. This formulation was uniformly sprayed on 2 
similar pots of 24-day-old plants (approximately 15 to 25 plants per pot) 
at a dose of 33 microgram/cm.sup.2. After the plants had dried, they were 
placed in a greenhouse and then watered intermittently at their bases, as 
needed. The plants were observed periodically for phytotoxic effects and 
physiological and morphological responses to the treatment. After 3 weeks, 
the herbicidal effectiveness of the compound was rated based on these 
observations. A 0-to-100 scale was used, 0 representing no phytotoxicity 
and 100 representing complete kill. The results of these tests appear in 
Table I. 
EXAMPLE 3 
Herbicidal Test 
By a procedure similar to that of Example 2 
1-(2-hydroxymethylpyrrolidinyl)-o-fluorocarboxanilide (A) and 
1-(2-methylpyrrolidinyl)-o-fluorocarboxanilide (B) were tested for the 
control of several broadleaf weeds. The weeds tested, test concentration 
and results are tabulated in Table II. 
TABLE II 
______________________________________ 
Herbicidal Effectiveness 
Compound 
Lbs/Acre Lambsquarter 
Mustard Pigsweed 
______________________________________ 
A 2.5 99 100 100 
0.98 98 98 100 
0.39 96 95 100 
0.16 97 37 100 
B 2.5 99 100 100 
0.98 100 89 100 
0.39 80 30 57 
0.16 40 10 17 
______________________________________ 
table 
__________________________________________________________________________ 
structure Melting Point and Herbicidal Effectiveness of 
1-(2-hydroxymethylpyrrolidinyl)carboxanilide 
##STR4## 
Melting 
Herbicidal Effectiveness: Pre/Post 
No. 
Xn Point, .degree. C 
0 W C L M P 
__________________________________________________________________________ 
1 4-Cl 112-115 
0/25 
50/50 
25/35 
93/100 
40/70 
45/100 
2 H 108-110 
30/0 40/25 
0/20 
85/90 
88/90 
88/75 
3 2-F 127-129 
90/40 
95/90 
55/50 
100/100 
98/95 
98/100 
4 3,4-Cl.sub.2 
156-157 
0/0 0/0 0/0 100/0 
20/0 100/0 
5 2-Cl 140-141 
10/0 30/20 
30/10 
98/70 
90/15 
100/80 
6 2-CH.sub.2 
124-125 
30/0 50/0 10/10 
95/60 
85/45 
98/90 
7 4-F 101-106 
45/10 
50/40 
60/30 
98/100 
98/60 
100/95 
8 3-F 111-112 
50/0 80/50 
70/25 
100/100 
100/.gamma. 
100/100 
9 3-CF.sub.3 
113 35/0 25/0 20/0 98/98 
70/65 
98/100 
10 3-CH.sub.3 
121-125 
10/25 
70/70 
60/25 
100/100 
100/60 
100/100 
11 4-CH.sub.3 
129-130 
20/0 20/0 20/0 98/93 
20/30 
65/95 
12* 
2-F 112-113 
95/65 
98/100 
88/75 
93/100 
100/95 
98/100 
13* 
C-CF.sub.3 
101-102 
60/15 
65/15 
65/15 
100/100 
100/80 
95/100 
14* 
3-F 101-102 
93/25 
98/100 
95/68 
98/95 
100/60 
100/100 
__________________________________________________________________________ 
*d,l-enantiomers- 
O = Wild Oats (Avena fatua) 
W = Watergrass (Echinochloa crusgalli) 
C = Crabgrass (Digitaria sanguinalis) 
L = Mustard (Brassica arvensis) 
M = Pigweed (Amaranthus retroflexus) 
P = Lambsquarter (Chenopodium album)